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Journal articles on the topic 'Synthetic Amphiphiles'

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Published: 18 May 2024

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1

Lombardo, Domenico, Mikhail A. Kiselev, Salvatore Magazù, and Pietro Calandra. "Amphiphiles Self-Assembly: Basic Concepts and Future Perspectives of Supramolecular Approaches." Advances in Condensed Matter Physics 2015 (2015): 1–22. http://dx.doi.org/10.1155/2015/151683.

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Amphiphiles are synthetic or natural molecules with the ability to self-assemble into a wide variety of structures including micelles, vesicles, nanotubes, nanofibers, and lamellae. Self-assembly processes of amphiphiles have been widely used to mimic biological systems, such as assembly of lipids and proteins, while their integrated actions allow the performance of highly specific cellular functions which has paved a way for bottom-up bionanotechnology. While amphiphiles self-assembly has attracted considerable attention for decades due to their extensive applications in material science, drug and gene delivery, recent developments in nanoscience stimulated the combination of the simple approaches of amphiphile assembly with the advanced concept of supramolecular self-assembly for the development of more complex, hierarchical nanostructures. Introduction of stimulus responsive supramolecular amphiphile assembly-disassembly processes provides particularly novel approaches for impacting bionanotechnology applications. Leading examples of these novel self-assembly processes can be found, in fact, in biosystems where assemblies of different amphiphilic macrocomponents and their integrated actions allow the performance of highly specific biological functions. In this perspective, we summarize in this tutorial review the basic concept and recent research on self-assembly of traditional amphiphilic molecules (such as surfactants, amphiphile-like polymers, or lipids) and more recent concepts of supramolecular amphiphiles assembly which have become increasingly important in emerging nanotechnology.

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2

RICO-LATTES, ISABELLE, MURIEL BLANZAT, EMILE PEREZ, ELODIE SOUSSAN, and CRISTINA STEFANIU. "CATANIONIC SUGAR DERIVED AMPHIPHILES: FROM MOLECULES TO TARGETED BIOMIMETIC SYSTEMS." Biophysical Reviews and Letters 01, no. 04 (October 2006): 423–31. http://dx.doi.org/10.1142/s179304800600029x.

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In the course of our investigations of routes for general and convenient synthesis of amphiphiles derived from sugars, we reported new synthetic ways to prepare catanionic surfactants, polymers and dendrimers using unprotected lactose or lactobionic acid. Moreover we developed amphiphilic dendrimers bearing sugar polar heads. These compounds are of interest for their biological applications (mimics of natural ligands of proteins (e.g. gp 120 of HIV), encapsulation, vectorisation).

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3

Yu, Chunsong, Myunggi An, Meng Li, Charles Manke, and Haipeng Liu. "Structure-Dependent Stability of Lipid-Based Polymer Amphiphiles Inserted on Erythrocytes." Membranes 11, no. 8 (July 29, 2021): 572. http://dx.doi.org/10.3390/membranes11080572.

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Cell-based therapies have the potential to transform the treatment of many diseases. One of the key challenges relating to cell therapies is to modify the cell surface with molecules to modulate cell functions such as targeting, adhesion, migration, and cell–cell interactions, or to deliver drug cargos. Noncovalent insertion of lipid-based amphiphilic molecules on the cell surface is a rapid and nontoxic approach for modifying cells with a variety of bioactive molecules without affecting the cellular functions and viability. A wide variety of lipid amphiphiles, including proteins/peptides, carbohydrates, oligonucleotides, drugs, and synthetic polymers have been designed to spontaneously anchor on the plasma membranes. These molecules typically contain a functional component, a spacer, and a long chain diacyl lipid. Though these molecular constructs appeared to be stably tethered on cell surfaces both in vitro and in vivo under static situations, their stability under mechanical stress (e.g., in the blood flow) remains unclear. Using diacyl lipid-polyethylene glycol (lipo-PEG) conjugates as model amphiphiles, here we report the effect of molecular structures on the amphiphile stability on cell surface under mechanical stress. We analyzed the retention kinetics of lipo-PEGs on erythrocytes in vitro and in vivo and found that under mechanical stress, both the molecular structures of lipid and the PEG spacer have a profound effect on the membrane retention of membrane-anchored amphiphiles. Our findings highlight the importance of molecular design on the dynamic stability of membrane-anchored amphiphiles.

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4

Engberts, Jan B. F. N., and Dick Hoekstra. "Vesicle-forming synthetic amphiphiles." Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes 1241, no. 3 (December 1995): 323–40. http://dx.doi.org/10.1016/0304-4157(95)00008-9.

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5

Gokel, George W., and Saeedeh Negin. "Synthetic membrane active amphiphiles." Advanced Drug Delivery Reviews 64, no. 9 (June 2012): 784–96. http://dx.doi.org/10.1016/j.addr.2012.01.011.

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6

Verboni, Michele, Diego Romano Perinelli, Alessandro Buono, Raffaella Campana, Maurizio Sisti, Andrea Duranti, and Simone Lucarini. "Sugar-Based Monoester Surfactants: Synthetic Methodologies, Properties, and Biological Activities." Antibiotics 12, no. 10 (September 30, 2023): 1500. http://dx.doi.org/10.3390/antibiotics12101500.

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Glycolipids are biocompatible and biodegradable amphiphilic compounds characterized by a great scientific interest for their potential applications in various technological areas, including pharmaceuticals, cosmetics, agriculture, and food production. This report summarizes the available synthetic methodologies, physicochemical properties, and biological activity of sugar fatty acid ester surfactants, with a particular focus on 6-O-glucose, 6-O-mannose, 6-O-sucrose, and 6′-O-lactose ones. In detail, the synthetic approaches to this class of compounds, such as enzymatic lipase-catalyzed and traditional chemical (e.g., acyl chloride, Steglich, Mitsunobu) esterifications, are reported. Moreover, aspects related to the surface activity of these amphiphiles, such as their ability to decrease surface tension, critical micelle concentration, and emulsifying and foaming ability, are described. Biological applications with a focus on the permeability-enhancing effect across the skin or mucosa, antimicrobial and antifungal activities, as well as antibiofilm properties, are also presented. The information reported here on sugar-based ester surfactants is helpful to broaden the interest and the possible innovative applications of this class of amphiphiles in different technological fields in the future.

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7

Barthélémy, Philippe, and Michel Camplo. "Functional Amphiphiles for Gene Delivery." MRS Bulletin 30, no. 9 (September 2005): 647–53. http://dx.doi.org/10.1557/mrs2005.191.

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AbstractThe design of safe and efficient gene transfer vectors remains one of the key challenges in gene therapy. Despite their remarkable transfection efficiency, viral vectors suffer from known safety issues. Consequently, significant research activity has been undertaken to develop nonviral approaches to gene transfer during the last decade. Numerous academic and industrial research groups are investigating synthetic cationic vectors, such as cationic amphiphiles, with the objective of increasing the gene transfection activity. Within this area, the development of functional synthetic vectors that respond to local environmental effects have met with success. These synthetic vectors are based on mechanistic principles and represent a significant departure from earlier systems. Many of these systems for gene delivery in vitro and in vivo are discussed in this article.

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8

Shimizu, Toshimi, and Masakatsu Hato. "Aggregation morphology of synthetic peptidic amphiphiles." Thin Solid Films 180, no. 1-2 (November 1989): 179–83. http://dx.doi.org/10.1016/0040-6090(89)90070-9.

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9

Bellairs, Joseph, Ravand Samaeekia, Handan Acar, Matthew Tirrell, and James LaBelle. "Cathepsin-Cleavable BIM BH3 Peptide Amphiphiles Are Potent Inducers of Cellular Apoptosis." Blood 126, no. 23 (December 3, 2015): 4438. http://dx.doi.org/10.1182/blood.v126.23.4438.4438.

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Abstract The BCL-2 family of proteins forms a complex interaction network that regulates cellular life and death decisions and contributes to cancer development, maintenance, and chemoresistance. BH3 only member proteins (e.g. BIM) serve as cellular stress sentinels and, when triggered, signal irreversible activation of apoptosis through their α-helical BH3 death domains. These pro-apoptotic signals are normally held in check by the multidomain anti-apoptotic proteins (e.g. BCL-XL, MCL-1) but when they are unable to do so the multidomain pro-apoptotic proteins BAX and BAK induce cell death through pore formation in the mitochondrial outer membrane. Therapeutic manipulation of the BCL-2 family with BH3 mimetics (including small molecules and synthetic peptides) is an emerging paradigm in cancer treatment and immune modulation. The design of next-generation therapeutics based on the BIM BH3 helix offers the unique advantage of recapitulating BIM's natural capacity to directly target the full complement of anti- and pro-apoptotic BCL-2 proteins. Here, we utilize the highly active BH3 domain of BIM as part of a peptide amphiphile nanostructure designed to overcome malignant cell death blockade. Peptide amphiphiles consist of bioactive peptides linked to hydrophobic lipid-like tail groups. In aqueous solutions, amphiphiles spontaneously assemble into micelles. Micelle-based peptide delivery provides several advantages: single micelles deliver high concentration of peptides into cells, they stabilize peptide secondary structure(s), and they have the potential for combinatorial synthesis using multiple bioactive moieties targeting non-redundant cell death escape pathways. While the exact mechanism behind cellular uptake of peptide amphiphiles remains controversial, recent work has shown that peptide amphiphiles intracellularly traffic through lysosomes and endosomes. In order to prevent the bioactive peptides from being sequestered within these structures, a system of escape is needed. Lysosomes contain many well-characterized proteases, and cathepsin B has previously been utilized to release chemotherapeutics in the context of targetable antibody-based treatments. Here, we generate peptide amphiphiles with BIM BH3 peptides and show that these nanostructures are able to specifically bind recombinant BCL-2 proteins, are stable at physiologic temperatures and pH, quickly enter into cells, and induce dose-responsive apoptosis in malignant hematologic cancers as measured by viability and caspase 3/7 activation. We further demonstrate that incorporating a cathepsin B-cleavable linker between the BIM BH3 peptide and the hydrophobic tail within individual amphiphiles results in increased binding to recombinant BCL-2 proteins while also allowing for increased cellular uptake and mitochondrial localization leading to faster and more potent dose-dependent cytotoxicity and caspase activation in malignant cells. Thus, we have developed a modular and potentially targetable nanostructure that represents a new promising strategy for BCL-2 family modulation and apoptosis induction in cancer. Disclosures No relevant conflicts of interest to declare.

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10

Akhmedov, Alan A., Dmitriy N. Shurpik, Pavel L. Padnya, Alena I. Khadieva, Rustem R. Gamirov, Yulia V. Panina, Asiya F. Gazizova, Denis Yu Grishaev, Vitaliy V. Plemenkov, and Ivan I. Stoikov. "Supramolecular Amphiphiles Based on Pillar[5]arene and Meroterpenoids: Synthesis, Self-Association and Interaction with Floxuridine." International Journal of Molecular Sciences 22, no. 15 (July 26, 2021): 7950. http://dx.doi.org/10.3390/ijms22157950.

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In recent years, meroterpenoids have found wide biomedical application due to their synthetic availability, low toxicity, and biocompatibility. However, these compounds are not used in targeted drug delivery systems due to their high affinity for cell membranes, both healthy and in cancer cells. Using the approach of creating supramolecular amphiphiles, we have developed self-assembling systems based on water-soluble pillar[5]arene and synthetic meroterpenoids containing geraniol, myrtenol, farnesol, and phytol fragments. The resulting systems can be used as universal drug delivery systems. It was shown by turbidimetry that the obtained pillar[5]arene/synthetic meroterpenoid systems do not interact with the model cell membrane at pH = 7.4, but the associates are destroyed at pH = 4.1. In this case, the synthetic meroterpenoid is incorporated into the lipid bilayer of the model membrane. The characteristics of supramolecular self-assembly, association constants and stoichiometry of the most stable pillar[5]arene/synthetic meroterpenoid complexes were established by UV-vis spectroscopy and dynamic light scattering (DLS). It was shown that supramolecular amphiphiles based on pillar[5]arene/synthetic meroterpenoid systems form monodisperse associates in a wide range of concentrations. The inclusion of the antitumor drug 5-fluoro-2′-deoxyuridine (floxuridine) into the structure of the supramolecular associate was demonstrated by DLS, 19F, 2D DOSY NMR spectroscopy.

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11

TOYOTA, Taro, and Satoshi HONDA. "Construction of Pseudo Cellular System by Synthetic Amphiphiles." Seibutsu Butsuri 56, no. 3 (2016): 165–67. http://dx.doi.org/10.2142/biophys.56.165.

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12

Kunjappu, Joy T., and P. Somasundaran. "Recent trends in bilayer formation of synthetic amphiphiles." Colloids and Surfaces A: Physicochemical and Engineering Aspects 117, no. 1-2 (October 1996): 1–5. http://dx.doi.org/10.1016/0927-7757(96)03636-9.

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13

Schrettl, Stephen, Emmanuel Contal, Tobias N. Hoheisel, Martin Fritzsche, Sandor Balog, Ruth Szilluweit, and Holger Frauenrath. "Facile synthesis of oligoyne amphiphiles and their rotaxanes." Chemical Science 6, no. 1 (2015): 564–74. http://dx.doi.org/10.1039/c4sc03154g.

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Carbon-rich organic compounds containing a series of conjugated triple bonds (oligoynes) are relevant synthetic targets, but an improved access to oligoynes bearing functional groups would be desirable.

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14

Kong, Lingling, Kadi Liis Saar, Raphael Jacquat, Liu Hong, Aviad Levin, Hongze Gang, Ruqiang Ye, Bozhong Mu, and Tuomas P. J. Knowles. "Mechanism of biosurfactant adsorption to oil/water interfaces from millisecond scale tensiometry measurements." Interface Focus 7, no. 6 (October 20, 2017): 20170013. http://dx.doi.org/10.1098/rsfs.2017.0013.

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Many biological molecules are by their nature amphiphilic and have the ability to act as surfactants, stabilizing interfaces between aqueous and immiscible oil phases. In this paper, we explore the adsorption kinetics of surfactin, a naturally occurring cyclic lipopeptide, at hexadecane/water interfaces and compare and contrast its adsorption behaviour with that of synthetic alkyl benzene sulfonate isomers, through direct measurements of changes in interfacial tension upon surfactant adsorption. We access millisecond time resolution in kinetic measurements by making use of droplet microfluidics to probe the interfacial tension of hexadecane droplets dispersed in a continuous water phase through monitoring their deformation when the droplets are exposed to shear flows in a microfluidic channel with regular corrugations. Our results reveal that surfactin rapidly adsorbs to the interface, thus the interfacial tension equilibrates within 300 ms, while the synthetic surfactants used undergo adsorption processes at an approximately one order of magnitude longer timescale. The approach presented may provide opportunities for understanding and modulating the adsorption mechanism of amphiphiles on a variety of interfaces in the context of life sciences and industrial applications.

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15

Everaars, Marcel D., Antonius T. M. Marcelis, and Ernst J. R. Sudhölter. "Monolayer formation of synthetic ammonium amphiphiles carrying cyanobiphenyloxy mesogens." Thin Solid Films 242, no. 1-2 (April 1994): 78–82. http://dx.doi.org/10.1016/0040-6090(94)90505-3.

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16

Yadavalli, Srujana S., Qi Xiao, Samuel E. Sherman, William D. Hasley, Michael L. Klein, Mark Goulian, and Virgil Percec. "Bioactive cell-like hybrids from dendrimersomes with a human cell membrane and its components." Proceedings of the National Academy of Sciences 116, no. 3 (December 27, 2018): 744–52. http://dx.doi.org/10.1073/pnas.1811307116.

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Cell-like hybrids from natural and synthetic amphiphiles provide a platform to engineer functions of synthetic cells and protocells. Cell membranes and vesicles prepared from human cell membranes are relatively unstable in vitro and therefore are difficult to study. The thicknesses of biological membranes and vesicles self-assembled from amphiphilic Janus dendrimers, known as dendrimersomes, are comparable. This feature facilitated the coassembly of functional cell-like hybrid vesicles from giant dendrimersomes and bacterial membrane vesicles generated from the very stable bacterial Escherichia coli cell after enzymatic degradation of its outer membrane. Human cells are fragile and require only mild centrifugation to be dismantled and subsequently reconstituted into vesicles. Here we report the coassembly of human membrane vesicles with dendrimersomes. The resulting giant hybrid vesicles containing human cell membranes, their components, and Janus dendrimers are stable for at least 1 y. To demonstrate the utility of cell-like hybrid vesicles, hybrids from dendrimersomes and bacterial membrane vesicles containing YadA, a bacterial adhesin protein, were prepared. The latter cell-like hybrids were recognized by human cells, allowing for adhesion and entry of the hybrid bacterial vesicles into human cells in vitro.

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17

Mahadevegowda, Surendra H., and Mihaiela C. Stuparu. "Amphiphilic Corannulene Derivatives: Synthetic Access and Development of a Structure/Property Relationship in Thermoresponsive Buckybowl Amphiphiles." ACS Omega 2, no. 8 (August 25, 2017): 4964–71. http://dx.doi.org/10.1021/acsomega.7b00807.

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18

Berchel, M., O. Lozach, W. Berthe, S. Hernot, H. Couthon-Gourvès, A. Mottais, T. Le Gall, P. Midoux, T. Montier, and P. A. Jaffrès. "Synthetic phospholipids and phospho-bola-amphiphiles for nucleic acid delivery." Phosphorus, Sulfur, and Silicon and the Related Elements 191, no. 11-12 (July 22, 2016): 1485–87. http://dx.doi.org/10.1080/10426507.2016.1212049.

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19

Behr, Jean-Paul. "Gene Transfer with Synthetic Cationic Amphiphiles: Prospects for Gene Therapy." Bioconjugate Chemistry 5, no. 5 (September 1994): 382–89. http://dx.doi.org/10.1021/bc00029a002.

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20

Brandenburg, K., L. Hawkins, P. Garidel, J. Andrä, M. Müller, H. Heine, M. H. J. Koch, and U. Seydel. "Structural Polymorphism and Endotoxic Activity of Synthetic Phospholipid-like Amphiphiles†." Biochemistry 43, no. 13 (April 2004): 4039–46. http://dx.doi.org/10.1021/bi0361158.

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21

Okuyama, Kenji, Kenji Hoso, Nobuyuki Maki, and Hiromi Hamatsu. "Liquid crystal structures of bilayer-forming synthetic amphiphiles, dialkyldimethylammonium bromides." Thin Solid Films 203, no. 1 (August 1991): 161–71. http://dx.doi.org/10.1016/0040-6090(91)90526-4.

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22

SZOENYI, S., A. CAMBON, and H. J. WATZKE. "ChemInform Abstract: New Synthetic Strategy to Vesicle-Forming Perfluoroalkylated Amphiphiles." ChemInform 26, no. 5 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199505109.

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23

Brahmachari, Sayanti, Sisir Debnath, Sounak Dutta, and Prasanta Kumar Das. "Pyridinium based amphiphilic hydrogelators as potential antibacterial agents." Beilstein Journal of Organic Chemistry 6 (September 21, 2010): 859–68. http://dx.doi.org/10.3762/bjoc.6.101.

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The numerous applications of hydrogelators have led to rapid expansion of this field. In the present work we report the facile synthesis of amphiphilic hydrogelators having a quaternary pyridinium unit coupled to a hydrophobic long alkyl chain through an amide bond. Different amphiphiles with various hydrophobic chain length and polar head groups were rationally designed and synthesized to develop a structure-property relation. A judicious combination of hydrophilic and hydrophobic segments led to the development of pyridinium based amphiphilic hydrogelators having a minimum gelation concentration of 1.7%, w/v. Field emission scanning electronic microscopy (FESEM), atomic force microscopy (AFM), photoluminescence, FTIR studies, X-ray diffraction (XRD) and 2D NOESY experiments were carried out to elucidate the different non-covalent interactions responsible for the self-assembled gelation. The formation of three-dimensional supramolecular aggregates originates from the interdigitated bilayer packing of the amphiphile leading to the development of an efficient hydrogel. Interestingly, the presence of the pyridinium scaffold along with the long alkyl chain render these amphiphiles inherently antibacterial. The amphiphilic hydrogelators exhibited high antibacterial activity against both Gram-positive and Gram-negative bacteria with minimum inhibitory concentration (MIC) values as low as 0.4 μg/mL. Cytotoxicity tests using MTT assay showed 50% NIH3T3 cell viability with hydrogelating amphiphile 2 up to 100 μg/mL.

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24

Albanese, Paola, Simone Cataldini, Chloe Z. J. Ren, Nadia Valletti, Jlenia Brunetti, Jack L. Y. Chen, and Federico Rossi. "Light-Switchable Membrane Permeability in Giant Unilamellar Vesicles." Pharmaceutics 14, no. 12 (December 12, 2022): 2777. http://dx.doi.org/10.3390/pharmaceutics14122777.

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In this work, giant unilamellar vesicles (GUVs) were synthesized by blending the natural phospholipid 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) with a photoswitchable amphiphile (1) that undergoes photoisomerization upon irradiation with UV-A (E to Z) and blue (Z to E) light. The mixed vesicles showed marked changes in behavior in response to UV light, including changes in morphology and the opening of pores. The fine control of membrane permeability with consequent cargo release could be attained by modulating either the UV irradiation intensity or the membrane composition. As a proof of concept, the photocontrolled release of sucrose from mixed GUVs is demonstrated using microscopy (phase contrast) and confocal studies. The permeability of the GUVs to sucrose could be increased to ~4 × 10–2 μm/s when the system was illuminated by UV light. With respect to previously reported systems (entirely composed of synthetic amphiphiles), our findings demonstrate the potential of photosensitive GUVs that are mainly composed of natural lipids to be used in medical and biomedical applications, such as targeted drug delivery and localized topical treatments.

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25

Park, Kyeng Min. "Self‐sorted Compartmentalization by Simultaneous Use of Natural and Synthetic Amphiphiles." Chemistry – An Asian Journal 16, no. 22 (October 14, 2021): 3645–48. http://dx.doi.org/10.1002/asia.202100977.

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26

GOTO, Rensuke, Hiroyuki KUBO, and Shoji OKADA. "Liposomes prepared from synthetic amphiphiles. I. Their technetium labeling and stability." CHEMICAL & PHARMACEUTICAL BULLETIN 37, no. 5 (1989): 1351–54. http://dx.doi.org/10.1248/cpb.37.1351.

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27

Pakalns, T. "Cellular recognition of synthetic peptide amphiphiles in self-assembled monolayer films." Biomaterials 20, no. 23-24 (December 1999): 2265–79. http://dx.doi.org/10.1016/s0142-9612(99)00157-x.

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28

Wu, Hong, Zhan Yuin Ong, Shaoqiong Liu, Yan Li, Nikken Wiradharma, Yi Yan Yang, and Jackie Y. Ying. "Synthetic β-sheet forming peptide amphiphiles for treatment of fungal keratitis." Biomaterials 43 (March 2015): 44–49. http://dx.doi.org/10.1016/j.biomaterials.2014.11.052.

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29

Schuur, Boelo, Anno Wagenaar, André Heeres, and Erik H. J. Heeres. "A synthetic strategy for novel nonsymmetrical bola amphiphiles based on carbohydrates." Carbohydrate Research 339, no. 6 (April 2004): 1147–53. http://dx.doi.org/10.1016/j.carres.2004.01.021.

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30

Giustini, Mauro, Anna Maria Giuliani, and Giuseppe Gennaro. "Natural or synthetic nucleic acids encapsulated in a closed cavity of amphiphiles." RSC Advances 3, no. 23 (2013): 8618. http://dx.doi.org/10.1039/c3ra23208e.

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31

Lock, Lye Lin, Michelle LaComb, Kelly Schwarz, Andrew G. Cheetham, Yi-an Lin, Pengcheng Zhang, and Honggang Cui. "Self-assembly of natural and synthetic drug amphiphiles into discrete supramolecular nanostructures." Faraday Discussions 166 (2013): 285. http://dx.doi.org/10.1039/c3fd00099k.

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32

Cuccovia, Iolanda Midea, Eloi Feitosa, Hernan Chaimovich, Luis Sepulveda, and Wayne Reed. "Size, electrophoretic mobility, and ion dissociation of vesicles prepared with synthetic amphiphiles." Journal of Physical Chemistry 94, no. 9 (May 1990): 3722–25. http://dx.doi.org/10.1021/j100372a067.

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33

BEHR, J. P. "ChemInform Abstract: Gene Transfer with Synthetic Cationic Amphiphiles: Prospects for Gene Therapy." ChemInform 26, no. 2 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199502306.

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34

Kashapov, Ruslan, Gulnara Gaynanova, Dinar Gabdrakhmanov, Denis Kuznetsov, Rais Pavlov, Konstantin Petrov, Lucia Zakharova, and Oleg Sinyashin. "Self-Assembly of Amphiphilic Compounds as a Versatile Tool for Construction of Nanoscale Drug Carriers." International Journal of Molecular Sciences 21, no. 18 (September 22, 2020): 6961. http://dx.doi.org/10.3390/ijms21186961.

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This review focuses on synthetic and natural amphiphilic systems prepared from straight-chain and macrocyclic compounds capable of self-assembly with the formation of nanoscale aggregates of different morphology and their application as drug carriers. Since numerous biological species (lipid membrane, bacterial cell wall, mucous membrane, corneal epithelium, biopolymers, e.g., proteins, nucleic acids) bear negatively charged fragments, much attention is paid to cationic carriers providing high affinity for encapsulated drugs to targeted cells. First part of the review is devoted to self-assembling and functional properties of surfactant systems, with special attention focusing on cationic amphiphiles, including those bearing natural or cleavable fragments. Further, lipid formulations, especially liposomes, are discussed in terms of their fabrication and application for intracellular drug delivery. This section highlights several features of these carriers, including noncovalent modification of lipid formulations by cationic surfactants, pH-responsive properties, endosomal escape, etc. Third part of the review deals with nanocarriers based on macrocyclic compounds, with such important characteristics as mucoadhesive properties emphasized. In this section, different combinations of cyclodextrin platform conjugated with polymers is considered as drug delivery systems with synergetic effect that improves solubility, targeting and biocompatibility of formulations.

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35

Bhattacharya, Santanu, and S. N. Ghanashyam Acharya. "Vesicle and Tubular Microstructure Formation from Synthetic Sugar-Linked Amphiphiles. Evidence of Vesicle Formation from Single-Chain Amphiphiles Bearing a Disaccharide Headgroup†." Langmuir 16, no. 1 (January 2000): 87–97. http://dx.doi.org/10.1021/la990468j.

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36

Bock, H., R. C. Advincula, E. F. Aust, J. Käshammer, W. H. Meyer, S. Mittler-Neher, C. Fiorini, J. M. Nunzi, and W. Knoll. "Supramolecular Assemblies for Second Order Nonlinear Optics Stabilized by Electrostatic Interaction." Journal of Nonlinear Optical Physics & Materials 07, no. 03 (September 1998): 385–95. http://dx.doi.org/10.1142/s0218863598000296.

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Electrostatic interactions are being used instead of covalent linkage to stabilize orientational order in novel materials for second order nonlinear optics. In complex supramolecular architectures, this simplifies the variation of chromophores or polymeric backbones. Other molecules can readily be inserted into the system in order to tune optical or thermodynamic properties without synthetic effort. Noncentrosymmetric ultrathin films consisting of highly ordered "active-passive" AB-Y-type multilayers of NLO active ionic amphiphiles and an ionic polymeric buffer material have been obtained by the Langmuir-Blodgett-Kuhn (LBK) technique. Combination with self-assembly by adsorption from solution is demonstrated.

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37

Ortega-Arroyo, Jaime, Andrew J. Bissette, Philipp Kukura, and Stephen P. Fletcher. "Visualization of the spontaneous emergence of a complex, dynamic, and autocatalytic system." Proceedings of the National Academy of Sciences 113, no. 40 (September 16, 2016): 11122–26. http://dx.doi.org/10.1073/pnas.1602363113.

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Autocatalytic chemical reactions are widely studied as models of biological processes and to better understand the origins of life on Earth. Minimal self-reproducing amphiphiles have been developed in this context and as an approach to de novo “bottom–up” synthetic protocells. How chemicals come together to produce living systems, however, remains poorly understood, despite much experimentation and speculation. Here, we use ultrasensitive label-free optical microscopy to visualize the spontaneous emergence of an autocatalytic system from an aqueous mixture of two chemicals. Quantitative, in situ nanoscale imaging reveals heterogeneous self-reproducing aggregates and enables the real-time visualization of the synthesis of new aggregates at the reactive interface. The aggregates and reactivity patterns observed vary together with differences in the respective environment. This work demonstrates how imaging of chemistry at the nanoscale can provide direct insight into the dynamic evolution of nonequilibrium systems across molecular to microscopic length scales.

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Sharma, Komal, Shams Aaghaz, Indresh K. Maurya, Shivaprakash M. Rudramurthy, Shreya Singh, Vinod Kumar, Kulbhushan Tikoo, and Rahul Jain. "Antifungal evaluation and mechanistic investigations of membrane active short synthetic peptides-based amphiphiles." Bioorganic Chemistry 127 (October 2022): 106002. http://dx.doi.org/10.1016/j.bioorg.2022.106002.

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Thauvin, Cédric, Aurélia Perino, Emmanuel Contal, Emmanuelle Morin, Patrick Schultz, Stéphane Meunier, and Alain Wagner. "Programmed Dispersions of MWNTs in Aqueous Media by Coating with Photopolymerizable Synthetic Amphiphiles." Journal of Physical Chemistry C 115, no. 15 (March 29, 2011): 7319–22. http://dx.doi.org/10.1021/jp2000464.

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Akao, Tetsuyuki, Tetsurou Osaki, Jun-ya Mitoma, Akio Ito, and Toyoki Kunitake. "The Effect of Physico-Chemical Characteristics of Synthetic Cationic Amphiphiles on DNA Transfection." Chemistry Letters 20, no. 2 (February 1991): 311–14. http://dx.doi.org/10.1246/cl.1991.311.

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van Leeuwen, E. B. M., A. Y. van der Veen, D. Hoekstra, J. B. F. N. Engberts, M. R. Halie, J. van der Meer, and M. H. J. Ruiters. "Transfection of Small Numbers of Human Endothelial Cells by Electroporation and Synthetic Amphiphiles." European Journal of Vascular and Endovascular Surgery 17, no. 1 (January 1999): 9–14. http://dx.doi.org/10.1053/ejvs.1998.0677.

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Goto, Rensuke, and Yuko (Daicho) Ibuki. "Tissue distribution of liposomes prepared from synthetic amphiphiles after intraperitoneal injection into mice." Applied Radiation and Isotopes 45, no. 1 (January 1994): 57–62. http://dx.doi.org/10.1016/0969-8043(94)90148-1.

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Akao, Tetsuyuki, Tetsurou Osaki, Jun-ya Mitoma, Akio Ito, and Toyoki Kunitake. "Correlation between Physicochemical Characteristics of Synthetic Cationic Amphiphiles and Their DNA Transfection Ability." Bulletin of the Chemical Society of Japan 64, no. 12 (December 1991): 3677–81. http://dx.doi.org/10.1246/bcsj.64.3677.

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Wu, Hong, Shaoqiong Liu, Nikken Wiradharma, Zhan Yuin Ong, Yan Li, Yi Yan Yang, and Jackie Y. Ying. "Short Synthetic α-Helical-Forming Peptide Amphiphiles for Fungal Keratitis Treatment In Vivo." Advanced Healthcare Materials 6, no. 6 (January 12, 2017): 1600777. http://dx.doi.org/10.1002/adhm.201600777.

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Elliott, Elizabeth K, Megan M Daschbach, and George W Gokel. "Aggregation Behavior and Dynamics of Synthetic Amphiphiles That Self‐Assemble to Anion Transporters." Chemistry - A European Journal 14, no. 19 (June 27, 2008): 5871–79. http://dx.doi.org/10.1002/chem.200800148.

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Wu, Fang-Yi, and Hsin-Chieh Lin. "Synthesis, Self-Assembly, and Cell Responses of Aromatic IKVAV Peptide Amphiphiles." Molecules 27, no. 13 (June 27, 2022): 4115. http://dx.doi.org/10.3390/molecules27134115.

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Synthetic bioactive aromatic peptide amphiphiles have been recognized as key elements of emerging biomedical strategies due to their biocompatibility, design flexibility, and functionality. Inspired by natural proteins, we synthesized two supramolecular materials of phenyl-capped Ile-Lys-Val-Ala-Val (Ben-IKVAV) and perfluorophenyl-capped Ile-Lys-Val-Ala-Val (PFB-IKVAV). We employed UV-vis absorption, fluorescence, circular dichroism, and Fourier-transform infrared spectroscopy to examine the driving force in the self-assembly of the newly discovered materials. It was found that both compounds exhibited ordered π-π interactions and secondary structures, especially PFB-IKVAV. The cytotoxicity of human mesenchymal stem cells (hMSCs) and cell differentiation studies was also performed. In addition, the immunofluorescent staining for neuronal-specific markers of MAP2 was 4.6 times (neural induction medium in the presence of PFB-IKVAV) that of the neural induction medium (control) on day 7. From analyzing the expression of neuronal-specific markers in hMSCs, it can be concluded that PFB-IKVAV may be a potential supramolecular biomaterial for biomedical applications.

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Goto, Rensuke. "Tissue distribution of 99mic-labeled liposomes prepared from synthetic amphiphiles containing amino acid residues." Journal of Liposome Research 4, no. 2 (January 1994): 877–905. http://dx.doi.org/10.3109/08982109409018607.

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Baccile, Niki, Ghazi Ben Messaoud, Patrick Le Griel, Nathan Cowieson, Javier Perez, Robin Geys, Marilyn De Graeve, Sophie L. K. W. Roelants, and Wim Soetaert. "Palmitic acid sophorolipid biosurfactant: from self-assembled fibrillar network (SAFiN) to hydrogels with fast recovery." Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences 379, no. 2206 (August 2, 2021): 20200343. http://dx.doi.org/10.1098/rsta.2020.0343.

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Nanofibres are an interesting phase into which amphiphilic molecules can self-assemble. Described for a large number of synthetic lipids, they were seldom reported for natural lipids like microbial amphiphiles, known as biosurfactants. In this work, we show that the palmitic acid congener of sophorolipids (SLC16:0), one of the most studied families of biosurfactants, spontaneously forms a self-assembled fibre network (SAFiN) at pH below 6 through a pH jump process. pH-resolved in situ small-angle X-ray scattering (SAXS) shows a continuous micelle-to-fibre transition, characterized by an enhanced core–shell contrast between pH 9 and pH 7 and micellar fusion into a flat membrane between pH 7 and pH 6, approximately. Below pH 6, homogeneous, infinitely long nanofibres form by peeling off the membranes. Eventually, the nanofibre network spontaneously forms a thixotropic hydrogel with fast recovery rates after applying an oscillatory strain amplitude out of the linear viscoelastic regime: after being submitted to strain amplitudes during 5 min, the hydrogel recovers about 80% and 100% of its initial elastic modulus after, respectively, 20 s and 10 min. Finally, the strength of the hydrogel depends on the medium's final pH, with an elastic modulus fivefold higher at pH 3 than at pH 6. This article is part of the theme issue ‘Bio-derived and bioinspired sustainable advanced materials for emerging technologies (part 1)’.

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Liu, Tao, Chunyan Bao, Haiyan Wang, Linbo Fei, Rongyan Yang, Yitao Long, and Linyong Zhu. "Self-assembly of crown ether-based amphiphiles for constructing synthetic ion channels: the relationship between structure and transport activity." New J. Chem. 38, no. 8 (2014): 3507–13. http://dx.doi.org/10.1039/c4nj00297k.

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Lang, Erin N., and Shelley A. Claridge. "Cow-to-cow variation in nanocrystal synthesis: learning from technical-grade oleylamine." Nanotechnology 33, no. 8 (December 2, 2021): 082501. http://dx.doi.org/10.1088/1361-6528/ac39cb.

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Abstract Many technical-grade reagents, including oleylamine, are broadly used as ligands in nanocrystal synthesis, allowing for cost-effective, and more environmentally friendly, preparation of materials in useful quantities. Impurities can represent 30% or more of these reagent blends, and have frequently emerged as substantial drivers of nanocrystal morphology, assembly, or other physical properties, making it important to understand their composition. Some functional alkyl reagents are derived from natural sources (e.g. often beef tallow, in the case of oleylamine), introducing alkyl chain structures very different than those that might be expected as side products of synthesis from pure feedstocks. Additionally, impurities can exhibit variations based on biological factors (e.g. species, diet, season). In biology, blends of alkyl chains allow for surprisingly sophisticated function of amphiphiles in the cell membrane, pointing to the possibility of similar control in synthetic materials if reagent composition were either better controlled or better understood. Here, we provide brief context on the breadth of roles technical-grade impurities have played in nanocrystal materials, followed by a perspective on oleylamine impurities, their physical properties, and their potential contributions to nanomaterial function.

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