Applications of functional surfactants

Recent studies have reported the introduction of a range of new chemical and biochemical functionalities into the structures of amphiphilic molecules. Assemblies spontaneously formed by these amphiphiles are in many cases highly complex and possess properties not found in systems formed from amphiphiles with simpler structures. In particular, the incorporation of peptides and oligopeptides into the hydrophilic domains of amphiphiles has led to new classes of surfactants that self-assemble into structures that mimic a variety of the functions of natural materials (including organic scaffolds of bone; inhibitors of proteins involved in viral infection; chiral polymeric amphiphiles; materials that promote adhesion of cells to surfaces). Amphiphiles functionalized with a range of carbohydrates have also been reported. These amphiphiles assemble into aggregate morphologies that depend strongly on the stereochemistry of the carbohydrate. These assemblies offer the basis of promising approaches for the design of polyvalent (potent) carbohydrate-based drugs. Finally, the introduction of redox-active and polymerizable functional groups into the structures of amphiphiles has provided the basis of a class of novel tunable solvents with potential applications in separations technologies as well as new materials that exhibit controlled release and catalytic properties.

[1]  B. Schade,et al.  Odd−Even Effects in Supramolecular Assemblies of Diamide Bolaamphiphiles† , 2000 .

[2]  Craig A. Rosslee,et al.  Active control of interfacial properties , 2000 .

[3]  Gray,et al.  Heterogeneous Catalysis with Cross-Linked Lyotropic Liquid Crystal Assemblies: Organic Analogues to Zeolites and Mesoporous Sieves. , 1999, Angewandte Chemie.

[4]  R. Zutshi,et al.  Targeting the dimerization interface for irreversible inhibition of HIV-1 protease. , 2000, Bioorganic & medicinal chemistry letters.

[5]  M. Shultz,et al.  Small‐Molecule Inhibitors of HIV‐1 Protease Dimerization Derived from Cross‐Linked Interfacial Peptides , 2000 .

[6]  M. Abe,et al.  Reversible Release Control of an Oily Substance Using Photoresponsive Micelles , 2001 .

[7]  E. Kaler,et al.  The Phase Behavior and Microstructure of Efficient Cationic–Nonionic Microemulsions , 2001 .

[8]  Raymond A. Dwek,et al.  Glycobiology: Toward Understanding the Function of Sugars. , 1996, Chemical reviews.

[9]  Shah,et al.  Electrochemical principles for active control of liquids on submillimeter scales , 1999, Science.

[10]  B. Bondurant,et al.  PHOTOINDUCED DESTABILIZATION OF STERICALLY STABILIZED LIPOSOMES , 1998 .

[11]  N. Abbott,et al.  Using Light to Control Dynamic Surface Tensions of Aqueous Solutions of Water Soluble Surfactants , 1999 .

[12]  S. Saavedra,et al.  Quantitative Studies of Binding between Synthetic Galactosyl Ceramide Analogues and HIV-1 Gp120 at Planar Membrane Surfaces. , 2001, Angewandte Chemie.

[13]  Y. Sanai,et al.  Involvement of Lipid Raft Signaling in Ganglioside-Mediated Neural Function , 2001 .

[14]  Principles for microscale separations based on redox-active surfactants and electrochemical methods. , 2001, Analytical chemistry.

[15]  Samuel I Stupp,et al.  Peptide-amphiphile nanofibers: A versatile scaffold for the preparation of self-assembling materials , 2002, Proceedings of the National Academy of Sciences of the United States of America.

[16]  N. Abbott,et al.  Reassessment of the surface activity of ferrocenyldimethylammonium surfactants , 2002 .

[17]  Shultz,et al.  Small-Molecule Inhibitors of HIV-1 Protease Dimerization Derived from Cross-Linked Interfacial Peptides This work was supported by NIH (GM52739) and NSF (9457372-CHE). , 2000, Angewandte Chemie.

[18]  M. Goto,et al.  Remarkably enhanced inhibitory effects of three-component hybrid liposomes including sugar surfactants on the growth of lung carcinoma cells. , 2002, Chemical & pharmaceutical bulletin.

[19]  Guangtao Li,et al.  Recognition Processes with Amphiphilic Carbohydrates in Water , 2002 .

[20]  Y Matsumoto,et al.  Highly specific inhibitory effect of three-component hybrid liposomes including sugar surfactants on the growth of glioma cells. , 2000, Bioorganic & medicinal chemistry letters.

[21]  K. Kjaer,et al.  Chiral Amplification of Oligopeptides in Two-Dimensional Crystalline Self-Assemblies on Water , 2002, Science.

[22]  H. Lodish.  Molecular Cell Biology , 1986 .

[23]  L. Kiessling,et al.  Strength in numbers: non-natural polyvalent carbohydrate derivatives. , 1996, Chemistry & biology.

[24]  C. Drummond,et al.  Polymerisation of liquid crystalline phases in binary surfactant/water systems , 1996 .

[25]  K. McGrath.  Polymerisation of liquid crystalline phases in binary surfactant/water systems , 1996 .

[26]  S. Raghavan,et al.  Microstructure and Dynamics of Wormlike Micellar Solutions Formed by Mixing Cationic and Anionic Surfactants , 2000 .

[27]  S. Friberg,et al.  Changed Lyotropic Liquid Crystalline Structure Due to Polymerization of the Amphiphilic Component , 1979, Science.

[28]  H. Sakai,et al.  Electrochemical Control of Vesicle Formation with a Double-Tailed Cationic Surfactant Bearing Ferrocenyl Moieties , 2001 .

[29]  Eric W. Kaler,et al.  Templating hollow polymeric spheres from catanionic equilibrium vesicles: Synthesis and characterization , 2000 .

[30]  Jason E. Gestwicki,et al.  Inter-receptor communication through arrays of bacterial chemoreceptors , 2002, Nature.

[31]  J. Behr,et al.  Dimerizable cationic detergents with a low cmc condense plasmid DNA into nanometric particles and transfect cells in culture. , 2001, Journal of the American Chemical Society.

[32]  Tushar H. Gore,et al.  Self-Assembly of Model Collagen Peptide Amphiphiles , 2001 .

[33]  A. Mueller,et al.  Photoinitiated destabilization of sterically stabilized liposomes. , 2001, Biochimica et biophysica acta.

[34]  G. Ourisson,et al.  Formation of giant vesicles from diacylmannosylerythritols, and their binding to concanavalin A , 2000 .

[35]  George M Whitesides,et al.  Polyvalent Interactions in Biological Systems: Implications for Design and Use of Multivalent Ligands and Inhibitors. , 1998, Angewandte Chemie.

[36]  Anja Mueller,et al.  Supramolecular materials via polymerization of mesophases of hydrated amphiphiles. , 2002, Chemical reviews.

[37]  D L Gin,et al.  Polymerization of a phosphonium diene amphiphile in the regular hexagonal phase with retention of mesostructure. , 2001, Journal of the American Chemical Society.

[38]  I. Rico-Lattes,et al.  First Example of Helices and Tubules in Aqueous Solution of a New Fluorescent Catanionic Sugar Surfactant , 2001 .

[39]  Rate-Dependent Lowering of Surface Tension during Transformations of Water-Soluble Surfactants from Bolaform to Monomeric Structures , 1998 .