Model membranes: Developments in functional micelles and vesicles

Current Opinion in Chemical Biology

Volumn 3, Issue 6, 1999, Pages 730-735

  Scrimin, Paolo ^a   Tecilla, Paolo ^b  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOPHILE;

CELL VACUOLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DELIVERY SYSTEM; LIPID BILAYER; MEMBRANE MODEL; MEMBRANE PERMEABILITY; MICELLE; REVIEW;

EID: 0032705164     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(99)90031-5     Document Type: Review

References (41)

1. Scrimin P. Control of reactivity in aggregates of amphiphilic molecules. Hamilton A.D. Supramolecular Control of Structure and Reactivity. 1996;101-153 Wiley, Chichester.
2. Fuhrhop J.H., Köning J. Membranes and molecular assemblies: the synkinetic approach. 1994;The Royal Society of Chemistry, Cambridge.
3. Lasic D.D. Novel applications of liposomes. Trends Biotechnol. 16:1998;307-321.
4. Miller A.D. Cationic liposomes for gene therapy. Angew Chem Int Ed. 37:1998;1768-1785.
5. Rädler J.O., Koltover I., Salditt T., Safinya C.R. Structure of DNA-cation liposome complexes: DNA intercalation in multilamellar membranes in distinct interhelical packing regimes. Science. 275:1997;810-814.
6. Rui Y., Wang S., Low P.S., Thompson D.H. Diplasmenylcholine-folate liposomes: an efficient vehicle for intracellular drug delivery. J Am Chem Soc. 120:1998;11213-11218. Vesicles of acid-labile lipids release their content in biological fluids when the local pH decreases from neutral to ~5. Intracellular drug delivery is thus successfully achieved.
7. Bondurant B., O'Brien D.F. Photoinduced destabilization of sterically stabilized liposomes. J Am Chem Soc. 120:1998;13541-13542. Sterically stabilized liposomes containing a photopolymerizable lipid release their content upon photoirradiation. This could allow the problem of drug release from PEG-functionalized liposomes.
8. Armitage B.A., Bennett D.E., Lamparski H.G., O'Brien D.F. Polymerization and domain formation in lipid assemblies. Adv Polym Sci. 126:1996;53-84.
9. Scrimin P., Caruso S., Paggiarin N., Tecilla P.: Ln(III)-catalyzed cleavage of phosphate-functionalized synthetic lipids: real time monitoring of vesicle decapsulation. Langmuir 1999, in press. Vesicles of synthetic phospholipids are cleaved by addition of Ln(III) ions. The system allows the contemporaneous monitoring of the cleavage process as well as the release of the vesicle content.
10. Pak C.C., Ali S., Janoff A.S., Meers P. Triggerable liposomal fusion by enzyme cleavage of a novel peptide-lipid conjugate. Biochim Biophys Acta. 1372:1998;13-27. The covalent binding of a fusogenic peptide to a lipid inhibits its activity. Enzymatic cleavage of the covalent bond restores the activity leading to vesicle fusion and release of the liposome content.
11. Menger F.M., Keiper J.S. Digitonin as a chemical trigger for the selective transformation of giant vesicles. Angw Chem Int Ed. 37:1998;3433-3435. Addition of digitonin to solutions of giant liposomes (10-100 μm in diameter) results in the disruption of the aggregates. The process is monitored in real time by phase-contrast microscopy.
12. Menger F.M., Angelova M.I. Giant vesicles: imitating the cytological processes of cell membranes. Acc Chem Res. 31:1998;789-797.
13. Bucher P., Fischer A., Luisi P.L., Oberholzer T., Walde P. Giant vesicles as biochemical compartments: the use of microinjection techniques. Langmuir. 14:1998;2712-2721.
14. + channel is reported at 3.2 Å resolution. A turning point for molecular neurobiology as key structural features are, at last, provided.
15. de Mendoza J., Cuevas F., Prados P., Meadows E.S., Gokel G.W. A synthetic cation-transporting calix [4]arene derivative active in phospholipid bilayers. Angew Chem Int Ed. 37:1998;1534-1537.
16. Tedesco M.M., Ghebremariam B., Sakai N., Matile S. Modeling the selectivity of potassium channels with synthetic, ligand-assembled π slides. Angew Chem Int Ed. 38:1999;540-543. By controlling their clustering in a vesicular membrane via metal ion coordination to a proper lipid matrix, it is demonstrated that polyarene molecular rods provide very effective potassium channels.
17. Kumpf R.A., Dougherty D.A. A mechanism for ion selectivity in potassium channels: computational studies of cation-pi interactions. Science. 261:1993;1708-1710.
18. Sakai N., Majumdar N., Matile S. Self-assembled rigid-rod ionophores. J Am Chem Soc. 121:1999;4294-4295. Rigid rods of polyarenes interact via hydrogen-bonding in vesicular membranes leading to the formation of ion channels. By properly selecting the hydrogen-bonding subunits it should be possible to tune the formation of the channels.
19. Li C., Budge L.P., Driscoll C.D., Willardson B.M., Allman G.W., Savage P.B. Incremental conversion of outer-membrane permeabilizers into potent antibiotics for Gram-negative bacteria. J Am Chem Soc. 121:1999;931-940. By controlling the balance between electrostatic and hydrophobic interactions, amphiphilic cholic acid derivatives can be turned into potent antibiotics. The ability of the molecule to move from the exterior to the interior of the membrane is critical.
20. Kreimayer A., André F., Gouyette C., Huynh-Dinh T. Transmembrane transport of adenosine 5′-triphosphate using a lipophilic cholesteryl derivative. Angew Chem Int Ed. 37:1998;2853-2855. ATP is transported into liposomes by its covalent linkage to a cholesteryl derivative thus masking its hydrophilicity. Hydrolysis of the conjugate then leads to ATP release into the liposome. The technique can be potentially applied to other hydrophilic molecules or drugs.
21. Scrimin P., Veronese A., Tecilla P., Tonellato U., Monaco V., Formaggio F., Crisma M., Toniolo C. Metal ion modulation of membrane permeability induced by a polypeptide template. J Am Chem Soc. 118:1996;2505-2506.
22. Béven L., Duval D., Rebuffat S., Riddell F.G., Bodo B., Wróblewski H. Membrane permeabilization and antimycoplasmic activity of the 18-residue peptaibols, trichorzins PA. Biochim Biophys Acta. 1372:1998;78-90.
23. Duval D., Cosette P., Rebuffat S., Duclohier H., Bodo B., Molle G. Alamethicin-like behavior of new 18-residue peptaibols, trichorzins PA. Role of the C-terminal amino-alcohol in the ion channel forming activity. Biochim Biophys Acta. 1369:1998;309-319.
24. 35Cl-NMR study. Biochim Biophys Acta. 1372:1998;370-378.
25. de Silva P.A., Gunaratne H.Q.N., Gunnalaugsson T., Huxley A.J.M., McCoy C.P., Rademacher J.T., Rice T.E. Signaling recognition events with fluorescent sensors and switches. Chem Rev. 97:1997;1515-1566.
26. 2+ providing that the single components are self-assembled in a micellar matrix. The strategy allows the optimization of the system combinatorially, with very little synthetic effort.
27. Sasaki D.Y., Shnek D.R., Pack D.W., Arnold F.H. Metal-induced dispersion of lipid aggregates: a simple, selective, and sensitive fluorescent metal ion sensor. Angew Chem Int Ed. 34:1995;905-907.
28. 2+ is described. It does not rely on the intrinsic properties of the metal ion, rather on the control of pyrene clustering in a vesicular membrane. This is a further elaboration of a system described in [27].
29. Jonas U., Shah K., Norvez S., Charych D.H. Reversible color switching and unusual solution polymerization of hydrazide-modified diacetylene lipids. J Am Chem Soc. 121:1999;4580-4588. For the first time, a system has been devised where vesicles composed of diacetylene lipids respond reversibly to external stimuli (pH) by changing their colour. The system could find practical application in material science.
30. Okada S.Y., Peng S., Spevak W., Charych D.H. Color chromism of polydiacetylene vesicles. Acc Chem Res. 31:1998;229-239.
31. 2 lysis allows the easy monitoring of the activity of inhibitors of the enzyme using standard analysis wells.
32. 2. Anal Biochem \10. 232:1995;7-23.
33. Chiu D.T., Wilson C.F., Ryttsén F., Strömberg A., Farre C., Karlsson A., Nordholm S., Gaggar A., Modi B.P., Moscho A.et al. Chemical transformations in individual ultrasmall biomimetic containers. Science. 283:1999;1892-1895. The paper illustrates methodologies for the measurement of rates of chemical reactions within giant vesicles.
34. Wong K.K.W., Mann S. Small-scale structures in biomineralization and biomimetic materials chemistry. Curr Opin Coll Int Sci. 3:1998;63-68.
35. Ozin G.A., Chomski E., Khushalani D., MacLachlan M.J. Mesochemistry. Curr Opin Coll Int Sci. 3:1998;181-193.
36. Einaga Y., Sato O., Iyoda T., Fujishima A., Hashimoto K. Photofunctional vesicles containing Prussian blue and azobenzene. J Am Chem Soc. 121:1999;3745-3750. The intercalation of Prussian blue into vesicular bilayers composed of azobenzene-functionalized lipids allows one to control by irradiation the magnetic properties of the new material.
37. 2+ to the surface of vesicles containing a cholesterol derivative functionalized with a ligand subunit. LDH activity is inhibited by the metal ions.
38. Kikuchi J., Ogata T., Inada M., Murakami Y. Circular dichroism of an aromatic guest induced by a chiral steroid cyclophane in aqueous solution and synthetic bilayer membrane. Chem Lett. 1996:1996;71-772.
39. Lahiri J., Fate D.G., Ungashe S.B., Groves J.T. Multi-heme self-assembly in phospholipid vesicles. J Am Chem Soc. 118:1996;2347-2358.
40. van Esch J.H., Hoffman M.A.M., Nolte R.J.M. Reduction of nicotinamides, flavins, and manganese porphyrins by formate, catalyzed by membrane-bound rhodium complexes. J Org Chem. 60:1995;1599-1610.
41. 2. For the first time, high turnover numbers (comparable with those of the natural system) have been observed.