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Amphiphile

An amphiphile is a chemical compound possessing both hydrophilic (water-loving, polar) and lipophilic (fat-loving, non-polar) properties, typically consisting of a polar head group and a non-polar hydrocarbon tail.^[1] These dual characteristics enable amphiphiles to orient themselves at interfaces, reducing surface tension and stabilizing emulsions or dispersions in heterogeneous systems.^[2] Due to the hydrophobic effect in aqueous environments, amphiphiles spontaneously self-assemble above a critical concentration to form organized structures such as micelles, vesicles, bilayers, and nanotubes, which minimize unfavorable interactions between hydrophobic tails and water.^[3] Common examples include surfactants like soaps and detergents, phospholipids in cell membranes, and synthetic block copolymers designed for specific functionalities.^[2] Many lipids exhibit amphiphilic behavior, playing essential roles in biological membranes and compartmentalization.^[4] Amphiphiles have diverse applications across chemistry, biology, and materials science, including as emulsifiers in consumer products, carriers in drug delivery systems for targeted therapeutics, and scaffolds in tissue engineering for regenerative medicine.^[5] In nanotechnology, peptide amphiphiles self-assemble into nanofibers that mimic extracellular matrices, supporting cell adhesion and proliferation.^[6] Their ability to form biomimetic structures also extends to programmable bioengineering, such as nucleic acid amphiphiles for gene delivery and sensing applications.^[7]

Definition and Classification

Definition

An amphiphile is a term derived from the Greek roots "amphi," meaning both or double, and "philos," meaning loving or affinity, thus describing a substance with dual affinity for water and oil; the word was coined by Paul Winsor in 1948.^[8] At its core, an amphiphile is a molecule or chemical compound featuring both hydrophilic regions, which are polar and attract water, and hydrophobic regions, which are nonpolar and repel water, resulting in distinctive behavior at interfaces between polar and nonpolar environments.^[1] This dual nature enables amphiphiles to reduce surface tension and facilitate interactions in heterogeneous systems, such as emulsions or biological membranes.^[4] The terms amphiphile and amphipathic are often used synonymously to describe entities with hydrophilic and hydrophobic moieties, though amphiphile typically refers specifically to molecular compounds, whereas amphipathic can apply more broadly to any surface or structure exhibiting dual affinity properties.^[9] A key concept in characterizing amphiphiles is the hydrophilic-lipophilic balance (HLB), which quantifies the relative extent of hydrophilic and lipophilic character within the molecule on a scale from 0 (highly lipophilic, favoring oil solubility) to 20 (highly hydrophilic, favoring water solubility).^[10] HLB values guide the prediction of an amphiphile's behavior in formulations, such as its role in stabilizing emulsions. One common method to calculate HLB, particularly for ionic surfactants, is the Davies approach, which assigns numerical contributions to specific functional groups: the hydrophilic increments (H_i) for polar groups like sulfates (+38.7) or esters (+2.4), and the lipophilic decrements (C_i) for hydrocarbon chains like -CH_2 (-0.475) or -CH_3 (-0.475). The formula is given by

\text{HLB} = 7 + \sum H_i + \sum C_i

where the neutral value of 7 represents a balanced point, and the sums account for all relevant group contributions in the molecule.^[10] This method allows for empirical estimation based on molecular structure without experimental measurement.

Types of Amphiphiles

Amphiphiles are primarily classified based on the number of hydrophobic tails attached to the hydrophilic head group, which significantly influences their packing efficiency and self-assembly tendencies. Single-chain amphiphiles, such as the surfactant sodium dodecyl sulfate (SDS), feature one hydrophobic alkyl chain, enabling them to form spherical micelles at lower concentrations due to looser packing. In contrast, double-chain amphiphiles, exemplified by phospholipids like phosphatidylcholine, possess two hydrophobic tails, promoting tighter packing and the formation of more stable bilayer structures such as vesicles. This distinction arises from the geometric constraints imposed by the tail architecture, where double chains increase the hydrophobic volume relative to the head area.^[2]^[3] A key classification scheme divides amphiphiles according to the nature of their hydrophilic head group, particularly whether it is charged or uncharged, which affects interactions with solvents and counterions. Ionic amphiphiles bear charged head groups and are subdivided into anionic types (e.g., those with sulfate heads like SDS), cationic types (e.g., quaternary ammonium compounds such as cetyltrimethylammonium bromide), and zwitterionic types (e.g., betaines with both positive and negative charges in the head). Non-ionic amphiphiles, on the other hand, feature uncharged polar heads, such as polyether chains in compounds like polysorbate 80 (Tween 80), leading to milder interactions and better compatibility in sensitive formulations. Ionic amphiphiles often exhibit hydrophilic-lipophilic balance (HLB) values greater than 10, enhancing their water solubility compared to non-ionic counterparts.^[11] Specialized amphiphiles extend these classifications with unique architectures tailored for advanced functionalities. Bolaphiles (bolaamphiphiles) consist of two hydrophilic heads connected by a long hydrophobic chain, allowing for enhanced surface activity and lower critical micelle concentrations than conventional single-chain types.^[12] Peptide amphiphiles integrate bioactive peptide sequences as the hydrophilic component with alkyl chains as tails, enabling pH- or enzyme-responsive self-assembly into nanofibers. Nucleic acid amphiphiles, such as DNA-lipid conjugates, combine oligonucleotide sequences with hydrophobic lipid moieties and have emerged prominently since the 2010s for programmable nanostructures in biomedical contexts. Macrocyclic amphiphiles, including calixarenes modified with hydrophobic cavities and polar rims, form host-guest complexes due to their cyclic topology, facilitating selective encapsulation.^[13]^[7]^[14] The foundational understanding of amphiphile types traces back to Irving Langmuir's 1917 studies on monolayers at the air-water interface, where he first systematically classified amphiphilic behaviors based on molecular orientation and surface pressure, laying the groundwork for modern classifications.^[15]

Molecular Structure and Properties

Structural Components

Amphiphiles are characterized by a molecular architecture that features distinct structural components: a hydrophilic head group, a hydrophobic tail, and often a linker region connecting them. These elements confer the dual affinity for polar and nonpolar environments, enabling the molecule's amphiphilic behavior.^[1] The hydrophilic head group consists of polar or charged moieties that interact favorably with water. Common examples include uncharged groups such as hydroxyl (-OH) or thiol (-SH), as well as charged groups like carboxylate (-COOH or -COO^-), sulfate (-SO4^-), phosphate (-PO4^3- or derivatives), and ammonium (-NH3^+). In phospholipids, the phosphate group serves as a key example of a charged head that enhances water solubility through ionic interactions and hydrogen bonding.^[1]^[16] The hydrophobic tail is typically composed of nonpolar alkyl chains, ranging from C8 to C18 hydrocarbons in length, which provide the oil-soluble portion of the molecule. These chains can be saturated, such as straight-chain alkanes, or unsaturated with cis double bonds that introduce kinks, affecting molecular packing density. Branching in the alkyl chains, such as short alkyl substituents, can disrupt tight packing and influence stability in assemblies, while fluorination of the tail—replacing hydrogen with fluorine atoms—creates a more rigid, lipophobic interior due to the strong electronegativity and low polarizability of fluorine, altering hydrophobic interactions.^[17]^[18]^[19] Linker regions between the head and tail provide flexibility to the overall structure. In natural lipids, glycerol often serves as a flexible spacer, forming ester or ether bonds that connect the polar head to the lipid tails. Non-ionic synthetic amphiphiles may employ ether bonds as linkers, which offer stability and conformational freedom compared to ester linkages.^[20] A general representation of amphiphile structure is given by the formula R-(CH_2)_n-X, where R denotes the hydrophobic tail (often an alkyl group), X is the hydrophilic head, and n typically ranges from 8 to 18 carbons to achieve optimal amphiphilicity. Longer tails in this formula tend to lower the hydrophile-lipophile balance (HLB), increasing overall hydrophobicity.^[21]^[18] In biological amphiphiles, such as peptide-based ones, stereochemistry plays a crucial role, with chirality at carbon centers determining molecular recognition and interactions. For instance, L-amino acids predominate in natural peptides, imparting a specific handedness that influences conformational preferences and biocompatibility.^[22]

Key Physical Properties

Amphiphiles display limited aqueous solubility owing to their amphipathic structure, reaching a monolayer solubility limit prior to the onset of self-assembly processes.^[23] For ionic amphiphiles, the Krafft point represents the critical temperature at which solubility sharply increases and equals the critical micelle concentration (CMC), influenced by factors such as hydrocarbon chain length, with longer chains yielding higher Krafft points.^[24] Below this point, solubility is governed by the crystalline energy and hydration heat of the surfactant.^[25] A hallmark property of amphiphiles is their ability to adsorb at the water-air interface, significantly reducing surface tension from approximately 72 mN/m for pure water to values as low as 22 mN/m.^[26] This reduction arises from the orientation of hydrophilic heads toward water and hydrophobic tails away from it, stabilizing the interface.^[27] The extent of adsorption is quantified by the Gibbs adsorption isotherm:

\Gamma = -\frac{1}{RT} \frac{d\gamma}{d \ln C}

where \Gamma is the surface excess concentration, \gamma is the surface tension, C is the bulk concentration, R is the gas constant, and T is the temperature.^[28] Non-ionic amphiphiles tend to elevate the viscosity of aqueous solutions compared to ionic counterparts, with longer hydrophobic or polyoxyethylene chain lengths contributing to higher relative viscosities through enhanced molecular interactions.^[29] This viscosity increase, often amplified by electrolytes, impacts solution flow and stability.^[30] Additionally, non-ionic types excel in generating and stabilizing foams by lowering surface tension and forming viscoelastic films at air-water interfaces.^[31] The thermal stability of amphiphiles, particularly their melting points, is dictated by hydrophobic tail packing efficiency; even-numbered carbon chains generally pack more uniformly in crystals, resulting in higher melting points than odd-numbered chains, akin to alkane behavior.^[32] Ionic amphiphiles' properties, including solubility and surface activity, vary with pH and salinity due to counterion specificity, as described by the Hofmeister series, where chaotropic ions (e.g., I⁻) promote greater solubility and interfacial adsorption than kosmotropic ones (e.g., SO₄²⁻).^[33] These behaviors establish key thresholds for self-assembly, such as the CMC.^[23]

Self-Assembly Behaviors

Mechanisms of Self-Assembly

The self-assembly of amphiphiles in aqueous environments is primarily driven by thermodynamic forces that minimize the free energy of the system. The hydrophobic effect is the dominant contributor, arising from the entropy gain when structured water molecules surrounding the hydrophobic tails are released upon aggregation, allowing these tails to cluster together and reduce the solvent-exposed hydrophobic surface area. This entropic stabilization is complemented by enthalpic contributions from van der Waals attractions between the alkyl chains in the core of the aggregate, which further lower the energy state. Balancing these attractive forces are repulsive interactions among the hydrophilic head groups, including electrostatic repulsion for ionic amphiphiles and steric hindrance for nonionic ones, which dictate the aggregate size and curvature by preventing excessive packing.^[3] A key thermodynamic parameter governing self-assembly is the critical micelle concentration (CMC), defined as the minimum amphiphile concentration above which stable aggregates form spontaneously. The standard free energy of micellization, \Delta G_{\text{mic}}, is related to the CMC by the equation \Delta G_{\text{mic}} = RT \ln \text{[CMC](/page/CMC)}, where R is the gas constant and T is the absolute temperature; this reflects the equilibrium between monomers and aggregates.^[34] The CMC exhibits a logarithmic dependence on the hydrophobic chain length, typically decreasing exponentially with increasing number of carbon atoms n in the tail, as described by approximations such as \log \text{[CMC](/page/CMC)} \approx A - B n, where A and B are constants reflecting head group and chain contributions, respectively; for example, each additional methylene group reduces the CMC by a factor of about 10 for many surfactants. Kinetic aspects of self-assembly involve overcoming nucleation barriers, where small clusters of amphiphiles form unstable intermediates before growing into stable aggregates; these barriers arise from the energy penalty of exposing edges or interfaces during initial clustering.^[35] Relaxation times for reaching equilibrium can span from milliseconds for simple micelles to hours for complex structures, influenced by factors such as temperature, which accelerates diffusion and fusion rates, and additives like salts that modulate electrostatic barriers.^[36] Phase behavior of amphiphile solutions is captured in temperature-concentration phase diagrams, which delineate regions of isotropic micellar solutions, hexagonal or cubic phases, viscoelastic gels, and lamellar phases as functions of amphiphile concentration and temperature.^[37] At low concentrations and higher temperatures, spherical micelles predominate in the dilute L1 phase; increasing concentration or lowering temperature shifts the system toward ordered lyotropic phases like hexagonal (H1) or lamellar (Lα), driven by packing parameter changes and reduced thermal motion.^[38] Recent advances highlight ion-specific effects on self-assembly, governed by the Hofmeister series, where kosmotropic ions (e.g., SO₄²⁻) enhance structuring of water and promote tighter aggregate formation by strengthening hydrophobic interactions and lowering the CMC, while chaotropic ions (e.g., SCN⁻) disrupt water structure and raise the CMC by favoring monomer solvation or aggregate disruption.^[33] Studies as of 2025 have shown these effects modulate aggregate stability in colloidal and biological mimicry systems, with applications in tuning phase transitions via ion choice.^[39]^[40]

Common Aggregate Structures

Amphiphiles self-assemble into a variety of supramolecular structures in solution, with the hydrophobic effect primarily stabilizing the sequestered hydrophobic regions within these aggregates. One of the most prevalent structures is the micelle, typically spherical in aqueous environments where hydrophilic head groups face outward toward the solvent, forming a shell around a hydrophobic core of aggregated tails. This core-shell architecture solubilizes hydrophobic molecules and has a typical hydrodynamic radius of 2–10 nm, depending on the amphiphile chain length and aggregation number.^[41] In nonpolar solvents, reverse micelles form instead, inverting the geometry so that polar heads cluster inward to encapsulate water or polar guests, while hydrophobic tails extend into the surrounding medium.^[42] Vesicles, also known as liposomes, represent another key architecture, consisting of closed bilayer spheres that enclose an aqueous compartment. These can be unilamellar, with a single bilayer, or multilamellar, featuring concentric bilayers, and range in size from 20 nm for small unilamellar vesicles to several microns for larger or multilamellar forms, enabling entrapment of both hydrophilic and hydrophobic species.^[43] Beyond spherical micelles and vesicles, amphiphiles form diverse elongated or periodic structures such as cylindrical micelles, which are rod-like aggregates; planar bilayers, flat sheets of two opposed monolayers; hexagonal phases, arrays of packed cylindrical micelles arranged in a hexagonal lattice; and cubic phases, intricate three-dimensional networks that can be micelle-based or bicontinuous. The preferred geometry of these aggregates is largely governed by the molecular packing parameter P = \frac{v}{a l}, where v is the volume of the hydrophobic tail, a is the effective area per head group at the interface, and l is the extended length of the tail; spherical micelles predominate for P < \frac{1}{3}, cylindrical micelles for \frac{1}{3} \leq P \leq \frac{1}{2}, and bilayers or vesicles for \frac{1}{2} \leq P \leq 1.^[44]^[45] The specific aggregate structure is influenced by factors including the hydrophilic-lipophilic balance (HLB) value, which quantifies the relative affinity for water versus oil; amphiphile concentration, where higher levels favor elongated or higher-curvature forms; and salinity, as added electrolytes screen electrostatic repulsions between charged heads, often promoting tighter packing. These parameters can induce transitions between structures, such as from spherical micelles to vesicles upon increasing ionic strength or adjusting HLB.^[46]^[47]^[48] Recent advancements have expanded the repertoire of amphiphile aggregates, including peptide amphiphile nanofibers, which self-assemble into stable, high-aspect-ratio cylindrical structures for biomedical scaffolding, leveraging peptide sequences to tune rigidity and bioactivity. Additionally, toroidal micelles, doughnut-shaped rings with persistent curvature, have emerged in systems of amphiphilic block copolymers, offering unique topologies for encapsulation and responsive disassembly. Emerging dynamic structures include self-reproducing polymeric vesicles formed from nonamphiphilic precursors without biochemical components, mimicking primitive cellular replication, and ATP-regulated transient superstructures from peptide amphiphiles that enable responsive assembly/disassembly.^[49]^[50]^[51]^[52]

Biological Roles

Role in Cell Membranes

Amphiphiles, particularly phospholipids, form the fundamental structure of cell membranes through self-assembly into lipid bilayers driven by the hydrophobic effect.^[53] In eukaryotic cells, these bilayers exhibit striking asymmetry, with phosphatidylcholine predominantly located in the outer leaflet and phosphatidylethanolamine and phosphatidylserine enriched in the inner leaflet, a distribution maintained by ATP-dependent flippases, floppases, and scramblases.^[54] This asymmetry imparts distinct biophysical properties to each membrane leaflet, influencing protein function, membrane curvature, and signaling processes.^[55] The fluidity of these phospholipid bilayers is crucial for membrane integrity and function, modulated by the degree of unsaturation in the fatty acid tails; unsaturated chains introduce kinks that prevent tight packing, thereby increasing fluidity and enabling dynamic processes like protein mobility and vesicle trafficking.^[53] Cone-shaped amphiphiles, such as lysophospholipids with a single acyl chain, promote positive membrane curvature, facilitating specific vesicle budding processes such as COPII-mediated transport in the secretory pathway.^[56] Cell membranes act as selective barriers due to the hydrophobic core of the bilayer, which restricts the passage of polar molecules while allowing lipid-soluble substances to diffuse; cholesterol integrates into the bilayer to modulate packing density, increasing order in the liquid-ordered phase and reducing fluidity to enhance barrier stability without inducing rigidity.^[57] In evolutionary terms, amphiphilic molecules likely played a pivotal role in prebiotic protocell formation, where simple fatty acids self-assembled into vesicles under early Earth conditions, encapsulating reactive components and facilitating the transition to compartmentalized life.^[58] Certain amphiphilic molecules disrupt membrane integrity for defensive purposes; antimicrobial peptides (AMPs), which are amphiphilic and cationic, form pores through mechanisms like the carpet model—where they cover the membrane surface leading to detergent-like solubilization—or the toroidal pore model, in which they induce membrane bending to create water-filled channels lined by peptide and lipid headgroups, ultimately causing cell lysis.^[59]

Additional Biological Functions

Amphiphiles play diverse roles in cellular signaling beyond structural contributions, particularly through phosphoinositides that act as key regulators in second messenger pathways. Phosphatidylinositol 4,5-bisphosphate (PIP2), a prominent membrane-embedded amphiphile, undergoes hydrolysis by phospholipase C (PLC) enzymes in response to extracellular signals from G-protein-coupled receptors or receptor tyrosine kinases, yielding diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). DAG remains associated with the membrane to activate protein kinase C, while IP3 diffuses to trigger calcium release from intracellular stores, thereby amplifying signaling cascades essential for processes like neurotransmission and immune responses.^[60]^[61] In protein localization, glycosylphosphatidylinositol (GPI) anchors serve as amphiphilic tethers that covalently link proteins to the outer leaflet of cell membranes, facilitating their targeted delivery and function. These glycolipid structures, synthesized in the endoplasmic reticulum and attached post-translationally to the C-terminus of proteins, enable rapid lateral mobility within lipid rafts and protect proteins from proteolytic degradation. Examples include decay-accelerating factor in complement regulation and prion protein in neuronal signaling, where GPI anchoring ensures precise membrane association without transmembrane domains.^[62]^[63] Certain amphiphiles exhibit antimicrobial properties by exploiting their cationic and amphiphilic nature to disrupt bacterial membranes. Cationic antimicrobial peptides, such as magainins derived from frog skin, adopt α-helical conformations upon binding to negatively charged phospholipid bilayers of bacterial cells, forming pores that lead to membrane permeabilization and cell lysis. This mechanism contributes to innate immunity by selectively targeting prokaryotic membranes over eukaryotic ones due to differences in lipid composition and charge.^[64]^[65]^[66] Bile salts, steroidal amphiphiles produced in the liver, are crucial for lipid transport and digestion in the intestines by emulsifying dietary fats into micelles. These facially amphiphilic molecules, with hydrophilic α-faces and hydrophobic β-faces, solubilize cholesterol and triglycerides, enhancing the accessibility of lipases and promoting efficient absorption of lipid-derived nutrients in the small intestine. Their detergent-like action prevents fat precipitation and supports enterohepatic recirculation for reuse.^[67]^[68]^[69] Aberrant amphiphilic assemblies underlie pathological conditions, notably in Alzheimer's disease where amyloid-β (Aβ) peptides form toxic aggregates. The amphiphilic sequence of Aβ, featuring hydrophobic C-terminal regions and hydrophilic N-terminal segments, drives self-assembly into oligomers and fibrils that insert into neuronal membranes, disrupting ion homeostasis and synaptic function. These aggregates, a hallmark of the disease, promote neuroinflammation and cell death through aberrant membrane interactions.^[70]^[71]

Applications

Industrial Applications

Amphiphiles, particularly anionic surfactants such as linear alkylbenzene sulfonates (LAS), play a central role in the detergent industry by facilitating soil removal through the reduction of surface tension at interfaces, which enables the wetting, emulsification, and dispersion of oils and greases from fabrics and surfaces.^[72] This mechanism allows soils to be suspended in wash water and easily rinsed away, making LAS a staple in household and industrial cleaning formulations. The global market for surfactants specifically used in detergents is estimated at $25 billion in 2025, reflecting their widespread adoption driven by demand for effective cleaning agents.^[73] In the food and cosmetics sectors, amphiphiles function as emulsifiers to stabilize oil-in-water mixtures, preventing phase separation and ensuring product consistency. For instance, lecithin, a natural amphiphile derived from soy or eggs, is commonly added to mayonnaise to form stable emulsions by adsorbing at the oil-water interface and reducing interfacial tension.^[74] Similarly, in cosmetics, amphiphilic emulsifiers like those based on fatty alcohols or polysorbates are incorporated into creams to create smooth, homogeneous textures by bridging hydrophobic oils and aqueous phases. This emulsification relies briefly on self-assembly behaviors, such as micelle formation, which encapsulate oils and enhance stability during storage and application.^[75] Amphiphiles are also employed in enhanced oil recovery (EOR) processes within the petroleum industry, where they significantly lower the interfacial tension between crude oil and injected water or brine in reservoir rocks, thereby mobilizing trapped oil and improving extraction efficiency. Surfactant flooding techniques, often involving anionic or amphoteric amphiphiles, can reduce this tension to ultralow levels (e.g., below 0.01 mN/m), enabling oil droplets to deform and flow through narrow pore spaces.^[76] In materials science, amphiphilic block copolymers serve as compatibilizers in polymer blends, where their dual hydrophilic and hydrophobic segments localize at interfaces between immiscible phases, reducing interfacial energy and enhancing mechanical properties like toughness and adhesion. For example, copolymers such as polystyrene-block-polybutadiene are added to blends of polyolefins and engineering plastics to suppress phase coarsening and improve processability during melt blending.^[77] Environmental considerations have driven the shift toward biodegradable biosurfactants as sustainable alternatives to traditional synthetic amphiphiles, with rhamnolipids—glycolipid-based molecules produced by bacteria like Pseudomonas aeruginosa—gaining prominence for their high biodegradability (e.g., up to 92% over 30 days under aerobic conditions) and lower ecotoxicity compared to petroleum-derived surfactants.^[78] These biosurfactants are increasingly integrated into industrial formulations for detergents and EOR to minimize persistent environmental residues and comply with regulations like the EU's REACH framework.^[79]

Biomedical Applications

Amphiphiles play a pivotal role in biomedical applications, particularly in drug delivery systems where their self-assembling properties enable the encapsulation and targeted release of therapeutic agents. Liposomes, formed by amphiphilic phospholipids, serve as versatile carriers that protect drugs from degradation and enhance their bioavailability. A seminal example is Doxil, a PEGylated liposomal formulation of doxorubicin approved by the FDA in 1995 for treating Kaposi's sarcoma, ovarian cancer, and multiple myeloma, which reduces cardiotoxicity compared to free doxorubicin while maintaining efficacy through prolonged circulation and tumor accumulation.^[80]^[81] pH-sensitive amphiphiles further advance drug delivery by responding to the acidic microenvironment of tumors or endosomes, triggering controlled release. These systems often incorporate ionizable groups in lipid or polymer structures that protonate at low pH, destabilizing aggregates and facilitating payload delivery. For instance, pH-responsive liposomes have demonstrated improved intracellular uptake of anticancer drugs like doxorubicin in preclinical models, enhancing therapeutic indices by minimizing off-target effects.^[82]^[83] In gene therapy, cationic lipid nanoparticles—amphiphilic assemblies with positively charged headgroups—enable efficient delivery of nucleic acids by condensing them into stable complexes that cross cellular barriers. These nanoparticles were instrumental in the mRNA vaccines for COVID-19, such as the Pfizer-BioNTech and Moderna formulations authorized in 2020, where ionizable cationic lipids like ALC-0315 facilitate endosomal escape and cytosolic release of mRNA encoding the SARS-CoV-2 spike protein, eliciting robust immune responses with high efficacy rates exceeding 90% in clinical trials.^[84]^[85] Emerging nucleic acid amphiphiles, such as DNA or RNA conjugates with hydrophobic moieties like cholesterol or alkyl chains, enable programmable self-assembly into nanostructures for precise therapeutic control. These conjugates form micelles or vesicles that incorporate therapeutic oligonucleotides, allowing stimuli-responsive disassembly for targeted gene silencing or editing; recent advancements since 2023 highlight their use in siRNA delivery without cationic helpers, reducing toxicity while achieving high transfection efficiency in cell cultures.^[86]^[87] Amphiphilic contrast agents enhance magnetic resonance imaging (MRI) by integrating gadolinium chelates with hydrophobic tails that self-assemble into nanoparticles, improving relaxivity and tissue specificity. For example, amphiphilic Gd-DOTA derivatives form micelles that exhibit significantly higher r1 relaxivity (e.g., up to 11-fold compared to free Gd-DOTA complexes) due to water exchange optimization at the nanoparticle-water interface, enabling clearer visualization of tumors in preclinical MRI studies.^[88]^[89] Amphiphile-based nanoparticles also combat antimicrobial resistance by disrupting bacterial membranes or delivering antibiotics selectively. Antimicrobial peptides, inherently amphiphilic with hydrophobic and cationic domains, self-assemble into nanoparticles that penetrate Gram-negative biofilms, showing synergistic effects with conventional antibiotics and minimal resistance development in 2024-2025 studies on multidrug-resistant strains, demonstrating efficacy against multidrug-resistant bacteria in preclinical models.^[90]^[91]

Examples

Synthetic Examples

Synthetic amphiphiles are engineered molecules with tailored hydrophilic and hydrophobic moieties to enable controlled self-assembly and functionality in various applications. One prominent example is sodium dodecyl sulfate (SDS), a single-chain anionic surfactant with the chemical formula C_{12}H_{25}SO_{4}Na, commonly employed in laboratory protocols to denature proteins by disrupting their native structures through electrostatic and hydrophobic interactions.^[92]^[93] Another key synthetic amphiphile is cetyltrimethylammonium bromide (CTAB), a cationic surfactant featuring a long C16 alkyl chain attached to a trimethylammonium headgroup, utilized in DNA extraction processes to lyse cells and precipitate nucleic acids, as well as in templating the growth of nanoparticles like gold nanorods due to its ability to stabilize anisotropic structures.^[94]^[95] Tween 80, also known as polysorbate 80, represents a non-ionic synthetic amphiphile composed of polyoxyethylene sorbitan monooleate, where a sorbitan backbone is esterified with oleic acid and ethoxylated, serving as a stabilizer and solubilizer in pharmaceutical formulations, including vaccines, to prevent protein aggregation and enhance bioavailability.^[96]^[97] Gemini surfactants constitute a class of dimeric synthetic amphiphiles, featuring two hydrophobic tails linked by a hydrophilic spacer; for instance, the 12-2-12 variant consists of two C12 alkyl chains connected by an ethylene spacer to quaternary ammonium headgroups, exhibiting a significantly lower critical micelle concentration (CMC) compared to monomeric counterparts, which enhances their efficiency in micelle formation and surface activity.^[98] Fluorinated amphiphiles, such as those incorporating perfluoroalkyl chains, are designed with fluorocarbon segments to impart high gas solubility; perfluoroalkyl types, often emulsified for stability, are explored for oxygen delivery in artificial blood substitutes due to their capacity to dissolve and transport large volumes of O2 without toxicity in biomedical contexts.^[99]^[100]

Natural Examples

Phosphatidylcholine, commonly known as lecithin, is a naturally occurring zwitterionic phospholipid characterized by a hydrophilic choline head group attached to a hydrophobic diacylglycerol tail. It is primarily sourced from egg yolks, where it constitutes a significant portion of the phospholipid content, and from soybeans, which serve as a major commercial source for extraction.^[101]^[102] Sodium taurocholate is a bile salt produced in the liver from cholesterol, featuring a steroidal structure that renders it amphiphilic with a conjugated taurine group enhancing its polarity. As a key component of bile, it originates endogenously in mammals and facilitates fat emulsification in the digestive process.^[103]^[104] Rhamnolipids represent a class of anionic glycolipid biosurfactants synthesized by the bacterium Pseudomonas aeruginosa, consisting of rhamnose sugar moieties linked to β-hydroxy fatty acid chains. These microbial products are secreted extracellularly during bacterial growth, particularly under nutrient-limited conditions.^[105]^[106] Saponins are triterpenoid glycosides abundant in various plants, including quinoa (Chenopodium quinoa), where they are concentrated in the outer seed coat as a natural defense mechanism. These amphiphilic compounds exhibit strong foaming properties due to their aglycone sapogenin core attached to one or more sugar chains, making them effective natural surfactants.^[107]^[108] Sphingolipids encompass a diverse family of lipids derived from ceramide backbones, with glycosphingolipids featuring polar sugar head groups such as glucose or galactose. They are prominently found in neural tissues, particularly within the myelin sheaths that insulate nerve fibers in the central nervous system.^[109]^[110]

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Jun 22, 2021 · This mini-review focuses on the regulatory effects of chirality alteration on the structure and bioactivity of linear and cyclic peptide assemblies.
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Sugar-Based Surfactants: Effects of Structural Features on the ... - NIH
May 16, 2024 · To characterize the water solubility of most amphiphile molecules, especially the ionic surfactants, the Krafft point (Tk) is often used, ...2.2. Solubility · 3. Materials And Methods · 3.4. Physicochemical...
[24]
Krafft Point - an overview | ScienceDirect Topics
The Krafft point of the ionic surfactant is directly related to its hydrocarbon chain length: a higher Krafft point has a longer hydrocarbon chain.
[25]
Krafft temperature – Knowledge and References - Taylor & Francis
Below the Krafft point, the solubility of the surfactant is determined by the crystalline energy and heat of hydration of the system, in other words, it is a ...
[26]
Culture Medium Development for Microbial-Derived Surfactants ...
For example, biosurfactants can greatly reduce the surface tension of water from 72 mN/m to 22 mN/m [10]. Owing to these properties, biosurfactants can solve ...
[27]
Surfactant - an overview | ScienceDirect Topics
... surface and the surface tension is reduced. For example, a good surfactant can lower the surface tension of water from 72 to 35 mN/m and the interfacial tension ...
[28]
Tensiometric determination of Gibbs surface excess and micelle point
Aug 6, 2025 · Amphiphile adsorption at the air/water interface lowers the surface tension (γ) of the solution. After a critical surfactant concentration ...
[29]
Viscosities of anionic—nonionic mixed surfactant systems
The mixed systems having longer alkyl and/or polyoxyethylene chain lengths in the nonionic surfactant have a larger relative viscosity at any mixed ratio.
[30]
[PDF] Effect of Polyoxyethylene Chain Length and Electrolyte on the ...
Jan 1, 2003 · In the single systems, the relative viscosity of nonionic surfactant is greater than that of SDS, and increases with the increasing level of ...
[31]
From Individual Liquid Films to Macroscopic Foam Dynamics
Aug 23, 2022 · Solutions of amphiphilic polymers provide a great foam stabilizing effect even at relatively low concentrations where neither aggregation nor ...
[32]
Understanding the structure and dynamics of cationic surfactants ...
Sep 25, 2019 · The odd–even alternation in melting that is well-known for alkanes is also observed in these materials. Although for CnTAB, some solid ...
[33]
Hofmeister Series: Insights of Ion Specificity from Amphiphilic ...
Mar 20, 2020 · This review is aimed to supply a fresh and comprehensive understanding of Hofmiester phenomena in surfactants, polymers, colloids, and interface science.
[34]
Surfactant Self-Assembling and Critical Micelle Concentration
May 6, 2020 · Critical micelle concentration (CMC) is the main chemical–physical parameter to be determined for pure surfactants for their ...
[35]
Premicellar aggregation of amphiphilic molecules - AIP Publishing
Corresponding to the increase in the free-energy barrier, the aggregate lifetime increases from milliseconds at the lower bound of the premicellar region to ...<|control11|><|separator|>
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Self-Assembly Kinetics of Amphiphilic Dendritic Copolymers
The self-assembly occurs via a fast step and a slow step with different relaxation times. At the critical micelle concentration (CMC), the fusion of small ...
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3 Phase Diagrams Of Lyotropic Mixtures - Oxford Academic
The phase diagram is usually represented in an isobaric surface of temperature versus relative concentration of the amphiphile, as shown in Fig. 3.7. Other ...
[38]
[PDF] 1 Chapter 42 – PHASE DIAGRAMS FOR MICELLAR SYSTEMS A ...
A tie line is the line in the temperature-concentration phase diagram along which phase separation proceeds. The final product is a 2-phase mixture. Page 16. 16.
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Hofmeister Effects Shine in Nanoscience - 2023 - Wiley Online Library
May 21, 2023 · Hofmeister effects play a crucial role in nanoscience by affecting the physicochemical and biochemical processes.
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A Review of Polymeric Micelles and Their Applications - PMC
Jun 20, 2022 · The size of the micelles is in the range of 10 to 100 nm, and different shapes of micelles have been developed for applications.
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Self – assembly of model surfactants as reverse micelles in nonpolar ...
Opposed to micelles the phenomenon of self-assembly of amphiphilic molecules in nonpolar solvents gives rise to the emergence of aggregates known as reverse ...
[42]
Liposomes: structure, composition, types, and clinical applications
May 13, 2022 · Liposomes are spherical lipid vesicles (usually 50–500 nm in diameter particle size) ... multilamellar vesicle (MLV), and multivesicular vesicles ...
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Theory of self-assembly of hydrocarbon amphiphiles into micelles ...
Theory of self-assembly of hydrocarbon amphiphiles into micelles and bilayers. Jacob N. Israelachvili, D. John Mitchell and Barry W. Ninham ...Missing: packing | Show results with:packing
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Cubic and Hexagonal Liquid Crystals as Drug Delivery Systems - PMC
May 22, 2014 · The hexagonal phase is composed of cylindrical micelles packed in a hexagonal pattern (Figure 1(b)). In contrast to the cubic phase, the ...
[45]
Influence of the HLB parameter of surfactants on the dispersion ...
The objective of this study was to investigate the effect of HLB on the dispersion properties of brine in residue.
[46]
Effects of Salt and Surfactant on Interfacial Characteristics of Water ...
Based on Figure 11, the presence of salt (and increasing its concentration) lowers the repulsion between surfactant headgroups and causes the surfactant ...
[47]
Micelle-to-Vesicle Transition: A Time-Resolved Structural Study
Mar 29, 1999 · Amphiphilic molecules spontaneously self-assemble in solution into a variety of microstructures. While their equilibrium properties are well ...
[48]
Multifunctional peptide nanofiber coatings enhance bone ... - Nature
Aug 27, 2025 · Functionalization of conventional bone grafts with a tailored peptide amphiphile nanofiber mixture improves cellular response, osteogenic ...
[49]
Nanotoroids Self-Assembled from Bottlebrush Copolymers
Aug 6, 2025 · In conclusion, we design amphiphilic bottlebrush copolypeptoids, which spontaneously self-assemble into uniform toroidal micelles in aqueous ...
[50]
Cell Membranes - The Cell - NCBI Bookshelf - NIH
Lipids containing unsaturated fatty acids similarly increase membrane fluidity because the presence of double bonds introduces kinks in the fatty acid chains, ...
[51]
The ins and outs of phospholipid asymmetry in the plasma membrane
Lipid asymmetry provides the two sides of the plasma membrane with different biophysical properties and influences numerous cellular functions.
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Lipid asymmetry and membrane trafficking: Transbilayer distribution ...
The distribution and rearrangement of phospholipids (PLs) within the bilayer are tightly regulated, influencing membrane curvature, tension, and organization.
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Phospholipases and Membrane Curvature: What Is Happening at ...
Feb 3, 2023 · LysoPC has a bulky head group and a small hydrophobic portion, which results in an average cone shape and a P~0.4 [23]. On the other hand, the ...
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Cholesterol provides nonsacrificial protection of membrane lipids ...
Mar 5, 2018 · Cholesterol plays vital biophysical roles in monolayer and bilayer membranes. It increases the lipid-packing density and maintains high membrane fluidity.
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From Self-Assembled Vesicles to Protocells - PMC - PubMed Central
In this article, we first review some fundamentals of self-assembly and focus on important features of vesicles made from single chain amphiphiles. For further ...
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Latest developments on the mechanism of action of membrane ...
In the toroidal pore mechanism, AMP insertion into the membrane lead to asymmetric tension that forms pores by induced surface bending in membrane leaflets ...
[57]
Phosphoinositide-specific phospholipase C in health and disease
PIP2, which is located within the plasma membrane, is cleaved by PI-PLC enzymes, generating the two well-known second messengers, DAG and IP3. DAG remains bound ...
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Phosphatidylinositol(4,5)bisphosphate: diverse functions at the ...
Aug 26, 2020 · PLC hydrolyses PI(4,5)P2 resulting in the formation of the second messengers, IP3 and DAG. DAG is phosphorylated to PA at the plasma membrane by ...
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Glycosylphosphatidylinositol (GPI) Anchors: Biochemistry and Cell ...
The GPI anchor represents a posttranslational modification of proteins with a glycolipid and is used ubiquitously in eukaryotes and most likely in some Archaea, ...
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Intracellular transport of GPI‐anchored proteins | The EMBO Journal
In eukaryotic cells, a subset of proteins are attached to the external leaflet of the plasma membrane by a glycosylphosphatidylinositol (GPI) anchor.Gpi‐anchored Proteins Can... · Sorting Of Gpi‐anchored... · Additional Requirements For...
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Cationic Amphiphiles, a New Generation of Antimicrobials Inspired ...
Increasing the positive charge of an AMP by adding arginine, lysine, or histidine residues to the peptide sequence can also increase antibacterial activity. The ...
[62]
Magainin 2 in Action: Distinct Modes of Membrane Permeabilization ...
Antimicrobial peptides (AMPs) are short cationic peptides with an amphiphilic nature. They play an important role in the innate immunity of host organisms, ...
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Revealing the Mechanisms of Synergistic Action of Two Magainin ...
This review focuses on cationic amphipathic peptides of the magainin family which were studied extensively by biophysical approaches.Magainins Form Membrane... · Magainin Structural... · Figure 1<|separator|>
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Bile salts in digestion and transport of lipids - ScienceDirect.com
Because of their unusual chemical structure, bile salts (BS) play a fundamental role in intestinal lipid digestion and transport.
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Physiology, Bile Acids - StatPearls - NCBI Bookshelf
May 1, 2023 · The three main functions of bile acids are to (1) emulsify fat, (2) excrete cholesterol, and (3) have an antimicrobial effect.
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Interaction of Bile Salts with Model Membranes Mimicking the ...
Aug 4, 2015 · Bile salts (BS) are biosurfactants synthesized in the liver and secreted into the intestinal lumen where they solubilize cholesterol and ...
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Amyloid-β Peptide Interactions with Amphiphilic Surfactants
Apr 23, 2018 · The amphiphilic nature of the amyloid-β (Aβ) peptide associated with Alzheimer's disease facilitates various interactions with biomolecules ...
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Recent progress in understanding Alzheimer's β-amyloid structures
The formation of amyloid fibrils, protofibrils and oligomers from the β-amyloid (Aβ) peptide represents a hallmark of Alzheimer's disease.
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[PDF] Linear alkylbenzene sulfonate - American Cleaning Institute
LAS is an anionic surfactant that lowers the surface ten- sion of water, enabling soils and stains to loosen and release from fabrics and surfaces. LAS provides ...
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Surfactants for Detergents XX CAGR Growth Analysis 2025-2033
Rating 4.8 (1,980) Jul 8, 2025 · The market, estimated at $25 billion in 2025, is projected to maintain a healthy Compound Annual Growth Rate (CAGR) of approximately 5% from ...
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Emulsions: making oil and water mix - AOCS
Sep 27, 2024 · Egg yolk, the traditional emulsifier for mayonnaise and sauces, also contains lecithin. ... Surfactants are amphiphilic, meaning that they ...
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Emulsifier for Cosmetic - Types, Uses , Benefits & Limitations
Jul 18, 2025 · Amphoteric emulsifiers are emulsifiers that can exhibit both anionic and cationic properties. This depends on the pH of the surrounding ...
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Comprehensive Review on the Role of Surfactants in the Chemical ...
Jan 3, 2022 · Surfactants used in cEOR are instrumental in reducing interfacial tension (IFT) and altering the wettability of rock, which leads to additional oil recovery.
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Amphiphilic block copolymers of PtBA‐b‐PMMA as compatibilizers ...
Jul 21, 2006 · PET and PMMA were blended at various weight fractions. These blends were compatibilized by employing amphiphilic block copolymers of ...
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Microbial production of rhamnolipids: opportunities, challenges and ...
Aug 5, 2017 · Therefore, biosurfactants produced by microbial fermentation can be used to replace synthetic surfactants as environmental friendly alternatives ...
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Review Doxil® — The first FDA-approved nano-drug: Lessons learned
Doxil, the first FDA-approved nano-drug (1995), is based on three unrelated principles: (i) prolonged drug circulation time and avoidance of the RES due to the ...
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Liposomes: Biomedical Applications - Chonnam Medical Journal
Jan 25, 2021 · A PEGylated liposomal formulation of doxorubicin (Doxil) was the first FDA-approved nanosized anti-cancer drug delivery system. After the ...
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pH-Sensitive Biomaterials for Drug Delivery - PMC - PubMed Central
In this review, we will summarize some pH-sensitive drug delivery system for medical application, mainly focusing on the pH-sensitive linkage bonds and pH- ...
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A review of mechanistic insight and application of pH-sensitive ...
Feb 13, 2014 · The concept of pH-sensitive liposomes tremendously improves the intracellular delivery of various materials such as anti-tumor drugs, toxins, ...
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Lipid nanoparticles for mRNA delivery | Nature Reviews Materials
Aug 10, 2021 · In this Review, we discuss the design of lipid nanoparticles for mRNA delivery and examine physiological barriers and possible administration routes.
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mRNA-lipid nanoparticle COVID-19 vaccines: Structure and stability
In this review we discuss proposed structures of mRNA-LNPs, factors that impact mRNA-LNP stability and strategies to optimize mRNA-LNP product stability.
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Nucleic acid amphiphiles: Synthesis, properties, and applications
Nucleic acid amphiphiles, referring to nucleic acids modified with large hydrophobic groups, have been widely used in programmable bioengineering.
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Synthesis of RNA-Amphiphiles via Atom Transfer Radical ... - NIH
May 31, 2023 · RNA-amphiphiles are synthesized using a photoinduced ATRP of hydrophobic monomers from an organic-phase-soluble RNA macroinitiator, using a " ...
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PEGylated Amphiphilic Gd-DOTA Backboned-Bound Branched ...
Nov 9, 2023 · MRI contrast agents with high kinetic stability and relaxivity are the key objectives in the field. We previously reported that Gd-DOTA ...
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HP-DO3A-based amphiphilic MRI contrast agents and relaxation ...
Relaxation studies of the amphiphilic Gd(III) complexes revealed that long alkyl chains facilitated the formation of micelles in an aqueous solution and ...
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Antimicrobial peptide biological activity, delivery systems and ...
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https://pmc.ncbi.nlm.nih.gov/articles/PMC10389804/
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Denaturation of proteins by surfactants studied by the Taylor ... - NIH
Apr 20, 2017 · We applied TDA to study denaturation of β-lactoglobulin, transferrin, and human insulin by anionic surfactant sodium dodecyl sulfate (SDS).
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[PDF] Sodium Dodecyl Sulfate Page
Sodium Dodecyl Sulfate (SDS) is an anionic surfactant ... laboratory ... This unique structure allows SDS to act effectively as a surfactant, reducing.
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A Critical Review of the Use of Surfactant-Coated Nanoparticles in ...
Jun 9, 2021 · By this mechanism, cationic surfactants such as cetyltrimethylammonium bromide (CTAB) and didodecyldimethylammonium bromide (DDAB) are used ...
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[PDF] Self-assembly and alignment of semiconductor nanoparticles on ...
Apr 8, 2011 · The use of a cationic surfactant, cetyltrimethylammonium bromide (CTAB), was critical for the synthesis of well-defined semiconductor.
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Safety of Polysorbate 80 in the Oncology Setting - PMC
Polysorbate 80, also known as Tween 80, is a synthetic nonionic surfactant commonly used in food, cosmetics, and drug formulations as a solubilizer, stabilizer, ...
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API | polysorbate 80 - Clinical Drug Experience Knowledgebase
Polysorbate 80 is also used as an excipient in some European and Canadian influenza vaccines. Influenza vaccines contain 25 μg of polysorbate 80 per dose.
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Structure Activity Relationships in Alkylammonium C12-Gemini ... - NIH
Aug 20, 2013 · The studies with caffeine and ketoprofen revealed that the most effective gemini surfactant was the one with the shorter spacer, G12-2-12. The ...
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Semifluorinated Alkanes as New Drug Carriers—An Overview of ...
Apr 11, 2023 · The potential clinical applications for oxygen transport by SFAs as pure fluids into the lungs or as intravenous applications of SFA emulsions ...Missing: types | Show results with:types
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oxygen carriers perfluorocarbon: Topics by Science.gov
The aim of this study was to prove whether albumin-derived perfluorocarbon-based nanoparticles (capsules) can operate as a novel artificial oxygen carrier in a ...
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Perspectives on lecithin from egg yolk: Extraction, physicochemical ...
Egg yolk lecithin is a natural phospholipid mixture extracted and refined from egg yolk, and is an amphiphilic molecule. According to different types of ...
[98]
Choline | Linus Pauling Institute | Oregon State University
Although the term "lecithin" is synonymous with phosphatidylcholine when used in chemistry, commercial lecithins are usually prepared from soybean, sunflower, ...
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Absorption-Enhancing Effects of Bile Salts - PMC - NIH
Bile salts are amphipathic steroidal bio-surfactants that are derived from cholesterol in the liver [1,2,3]. The synthesis of bile salts is the major route for ...
[100]
Structural basis of sodium-dependent bile salt uptake into the liver
May 11, 2022 · The liver takes up bile salts from blood to generate bile, enabling absorption of lipophilic nutrients and excretion of metabolites and drugs.
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Rhamnolipid the Glycolipid Biosurfactant: Emerging trends and ...
Jan 4, 2021 · Rhamnolipids (RLs) are surface-active compounds and belong to the class of glycolipid biosurfactants, mainly produced from Pseudomonas aeruginosa.
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Rhamnolipids: diversity of structures, microbial origins and roles - NIH
Rhamnolipids are glycolipidic biosurfactants produced by various bacterial species, initially found as exoproducts of Pseudomonas aeruginosa.
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An Insight into Saponins from Quinoa (Chenopodium quinoa Willd)
Feb 27, 2020 · Saponins are an important group found in Chenopodium quinoa. They represent an obstacle for the use of quinoa as food for humans and animal feeds.
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Perspectives on Saponins: Food Functionality and Applications - NIH
In the context of food applications, saponins are utilized as natural emulsifiers, foaming agents, and stabilizers. They contribute to texture and stability in ...
[105]
Sphingolipids and Membrane Biology as Determined from Genetic ...
Glycosphingolipids (GSL) are complex sphingolipids that are synthesized from ceramides. They are extended by the sequential addition of sugar moieties and, in ...
[106]
Role of Sphingolipid Metabolism in Neurodegeneration - PMC
Sphingolipids are major components of oligodendrocytes and the myelin sheath. Abnormalities in sphingolipid metabolism have been described in MS (Vidaurre et al ...