Bilayer membranes and transporter models

Current Opinion in Chemical Biology

Volumn 1, Issue 4, 1997, Pages 497-505

  Fyles, Thomas M ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ION CHANNEL; PEPTIDE;

CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; LIPID BILAYER; MEMBRANE FUSION; PHYSIOLOGY; REVIEW; TRANSPORT AT THE CELLULAR LEVEL;

BIOLOGICAL TRANSPORT; ION CHANNELS; LIPID BILAYERS; MEMBRANE FUSION; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES;

EID: 0031317726     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(97)80044-0     Document Type: Article

References (55)

1. Gokel GW, Murillo O: Synthetic organic chemical models for transmembrane channels. Accounts Chem Res 1996, 29:425-432. A recent review of nonpeptide ion channel models which provides an excellent summary of the field up to early 1996.
2. Fyles TM, Van Straaten-Nijenhuis WF: Ion channel models. In Comprehensive Supramolecular Chemistry, vol 10. Edited by Reinhoudt DN, Oxford: Pergammon; 1996:53-77. A review of channel-forming systems in solid, liquid crystalline, and membrane states. The review is comprehensively covers advances up to mid-1995.
3. Bechinger B: Structure and functions of channel-forming peptides: magainins, cecropins, melittin, and alamethicin. J Membrane Biol 1997, 31563:197-211.
4. Koeppe III RE, Andersen OS: Engineering the gramicidin channel. Ann Rev Biomol Struct 1996, 25:231-258.
5. Molle G, Dugast J-Y, Spach G, Duclohier H: Ion channel stabilization of synthetic alamethicin analogs by rings of interhelix H-bonds. Biophysical J 1996, 70:1669-1675.
6. Lien L, Jaikaran DCJ, Zhang Z, Woolley GW: Photomodulated blocking of gramicidin ion channels. J Am Chem Soc 1996, 118:12222-12223. Gramicidin, derivatised with an azobenzene-alkylammonium tail linked to the carboxyl terminus via a carbamate linkage, shows channel blockage as a function of the cis-trans photoisomerisation of the azobenzene. This system reveals a potential mechanism for enhance channel regulation, by using two switches in series.
7. You S, Peng S, Lien L, Breed J, Sansom MSP, Woolley GA: Engineering stabilized ion channels: covalent dimers of alamethicin. Biochemistry 1996, 35:6225-6232. Alamethicin, dimerized via the carboxyl terminus using two flexible spans, gives alamethicin-like conductance states with specific stablization of some levels. These results are on the route to covalent clusters of peptides which might act in a protein-like fashion.
8. Åkerfeldt KS, Kienker PK, Lear JD, DeGrado WF: Structure and conduction mechanisms of minimalist ion channels. In Comprehensive Supramolecular Chemistry, vol 10. Edited by Reinhoudt DN, Oxford: Pergammon; 1996:659-686.
9. Lear JD, Schneider JP, Kienker PK, DeGrado WF: Electrostatic effects on ion selectivity and rectification in designed ion channel peptides. J Am Chem Soc 1997, 119:3212-2317. Amphipathic helical peptides bearing cationic, anionic, or neutral amino termini demonstrate that the head groups control ion selectivity electrostatically. The cationic derivative additionally shows current rectification.
10. 2H termini.
11. Das S, Lengweiler UD, Seebach D, Reusch RN: Proof for a non-proteinaceous calcium-selective channel in Escherichia coli by total synthesis from (R)-3-hydroxybutanoic acid and inorganic polyphosphate. Proc Natl Acad Sci USA 1997, 94: 9075-9079. Synthetic poly[(R)-3-hydroxybutanoate] oligomers (128 units) plus calcium polyphosphate (65 units) form channels which are functionally indistinguishable from naturally derived materials of the same composition. This is a remarkable structural proof carried out in the best traditions of natural products chemistry.
12. Meillon J-C, Voyer N: A synthetic transmembrane channel active in lipid bilayers. Angew Chem Int Ed 1997, 36:967-969,
13. Wagner H, Harms K, Koert U, Meder S, Boheim: Oligo-THF peptides: synthesis, membrane insertion, and studies of ion channel activity. Angew Chem Int Ed Engl 1996, 35:2643-2646.
14. Dubowchik GM, Firestone RA: A lipophilic polyamino-bolaamphiphile to dissipate pH gradients across a bilayer membrane: synthesis and proton transport Tetrahedron Lett 1996, 37:6465-6468.
15. Deng G, Dewa T, Regen SL: A synthetic ionophore that recognizes negatively charged phospholipid membranes. J Am Chem Soc 1996, 118:8975-8976.
16. Deng G, Merritt M, Yamashita K, Janout V, Sadownik A, Regen SL: Kinetic evidence for duplicity in ion transport J Am Chem Soc 1996, 118:3307-3308.
17. + transport through phospholipid bilayer membrane by a synthetic calix[4]arene carrier. Langmuir 1996, 12:2684-2689.
18. a values by NMR. J Org Chem 1996, 61:4676-4684.
19. Westmark PR, Gardiner SJ, Smith BD: Selective monosaccharide transport through lipid bilayers using boronic acid carriers. J Am Chem Soc 1996, 118:11093-11100.
20. Murillo O, Suzuki I, Abel E, Gokel GW: Sodium cation transport in synthetic channels obeys the Hammett relationship in a phospholipid bilayer membrane. J Am Chem Soc 1996, 118:7628-7629.
21. 3- NMR and bilayer clamp techniques.
22. Murillo O, Abel E, Maguire GEM, Gokel GW: A tris(macrocycle) that exhibits H-bond-induced blockage of the cation channel function in a phospholipid bilayer. Chem Commun 1996, 119:2147-2148. An indole terminated tris-macrocycle channel is inactive and molecular mechanics calculations suggest the channel portal is blocked by the head group.
23. Abel E, Maguire GEM, Meadows ES, Murillo O, Jin T, Gokel GW: Planar bilayer conductance and fluorescence syudies confirm the function and location of a synthetic, sodium-ion-conduction channel in a phospholipid bilayer membrane. J Am Chem Soc 1997, 119:9061-9062. Dansyl and N-methylindole terminated tris-macrocycle channels are active transporters (NMR technique). The solvent-dependent fluorescence and fluorescence quenching by doxyl lipids is consistent with an interfacial location of the head groups.
24. Fyles TM, Loock D, van Straaten-Nijenhuis WF, Zhou X: Pores formed by bis-macrocyclic Lola-amphiphiles in vesicle and planar bilayer membranes. J Org Chem 1996, 61:8866-8874. Bis-macrocyclic bolaamphiphiles induce cation selective transport via multiple copies of a single aggregate (probably a dimer) in planar and vesicle bilayer membranes.
25. Zhou X: Towards voltage-gated ion channels, molecular diodes. [PhD thesis]. Victoria: University of Victoria; 1997
26. Shinoda W, Namiki N, Okazaki, S: Molecular dynamics study of lipid bilayer: convergence, structure, and long-time dynamics. J Chem Phys 1997, 106:5721-5743.
27. Wilson MA, Pohorille A: Mechanism of unassisted ion transport across membrane bilayers. J Am Chem Soc 1996, 118:6580-6587.
28. Israelachvili JN: Intermolecular and surface forces. London: Academic press; 1985:251.
29. Kimizuka N, Wakiyama T, Miyauchi H, Yoshimi T, Tokuhiro M, Kunitake T: Formation of stable bilayer membranes in binary aqueous-organic media from a dialkyl amphiphile with a highly dipolar head group. J Am Chem Soc 1996, 118:5808-5809.
30. Bhattacharya S, De S: Modulation of vesicular properties by variation of shapes of bolaform counter ions in hybrid-ion paired surfactants. Chem Commun 1996, 1283-1284.
31. Nakano A, Hernandez JC, Dewall SL, Wang K, Berger DR, Gokel GW: Steroidal aza-lariat ethers: syntheses and aggregation behaviour. Supramol Chem 1997, 8:213-223.
32. Menger FM, Ding J: Spiro-surfactants and -phospholipids: synthesis and properties. Angew Chem Int Ed 1996, 35:2137-2139. The surfactant properties of corner-fused cyclobutane oligomer amphiphiles were impaired by the rigid chains. The rigid chains were expected to inhibit formation of micelles, and no clear critical micelle concentration was reached. A related phospholipid did form globular aggregates, contrary to the predictions of the packing parameter.
33. Menger FM, Wong Y-L: Synthesis of defective phospholipids. J Org Chem 1996, 61:7382-7390.
34. Pérez L, Torres JL, Manresa A, Solans C, Infante MR: Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compound from arginine, bis(Arg). Langmuir 1996, 12:5296-5301.
35. Muñoz S, Abel E, Want K, Gokel GW: Control of vesicle formation by chemical switching. Tetrahedron 1995, 51:423-434.
36. Sommerdijk NAJM, Lambermon MHL, Feiters MC, Nolte RJM, Zwaneneburg B: Boomerang shaped aggregates from a histidine surfactant Chem Commun 1997, 455-456.
37. Lu X, Zhang Z, Liang Y: Complexed bilayer membranes with novel structural features formed by single-chain amphiphiles. Langmuir 1997, 13:533-538.
38. Wang K, Muñoz S, Zhang L, Castro R, Kaifer AE, Gokel GW: Organometallic amphiphiles: oxidized ferrocene as headgroup for redox-switched bilayer and monolayer membranes. J Am Chem Soc 1996, 118:6707-6715. Mono and bis-ferrocene surfactants form redox-dependent aggregates. Bis-ferrocene amphiphiles do not form stable vesicles, but aggregate to monolayer bounded vesicles when oxidized to the bis-ferricinium form. This is one of the few examples where this process is reversible.
39. Muñoz S, Gokel GW: Organometallic amphiphiles: novel mechanisms for redox chemical control of aggregation behavior. Inorg Chim Acta 1996, 250:59-67.
40. Schmitt L, Tampé R: ATP-Lipids - protein anchor and energy sources in two dimensions. J Am Chem Soc 1996, 118:5532-5543.
41. Walker SA, Kennedy MT, Zasadzinski JA: Encapsulation of bilayer vesicle by self-assembly. Nature 1997, 387:61-64.
42. 4.
43. Tyson JC, Moore JL, Hughes KD, Collard DM: Amphiphilic cup-shaped [(4-alkylphenyl)azo]-substituted calixarenes: self-assembly and host-guest chemistry at the air-water interface. Langmuir 1997, 13:2068-2073.
44. Cha X, Ariga K, Kunitake T: Molecular recognition of aqueous dipeptides at multiple hydrogen-bonding sites of mixed peptide monolayers. J Am Chem Soc 1996, 118:9545-9551. Oligopeptide amphiphiles at the air-water interface recognize dipeptides in the subphase via hydrogen bonding interactions. Ternary complexes form with added amphiphilic benzoic acids. Ternary complexes involving insertion of amphiphilic benzoic acids between adjacent lipids also form as the dipeptide opens gaps in the monomer spacing within the monolayer.
45. Ebara Y, Itakura K, Okahata Y: Kinetic studies of molecular recognition based on hydrogen bonding at the air-water interface by using a highly sensitive quartz-crystal microbalance. Langmuir 1996, 12:5156-5170. Cyanurate lipids as a monolayer on a quartz crystal microbalance are able to recognize melamine and other hydrogen bonding guests in adjacent aqueous solution. The interaction energies correlate to the number and complementarity of the hydrogen bond donors and acceptors. The interfacial environment appears remarkably similar to homogeneous organic solution!
46. Fyles TM, Zeng B: Molecular recognition-controlled membrane disruption by a bis(crown ether) bola-amphiphile. Chem Commun 1996, 2295-2296.
47. Zeng B: Flexible ditopic receptors. [PhD thesis]. Victoria: University of Victoria; 1997.
48. Morigaki K, Dallavalle S, Walde P, Colonna S, Luisi PL: Autopoietic self-reproduction of chiral fatty acid vesicles. J Am Chem Soc 1997, 119:292-301. Enantiomerically pure 2-methyldodecanoic anhydride undergoes biphasic hydrolysis catalysed by vesicles of chiral and racemic forms of the acid in this work. Homochiral vesicles hydrolyse either enantiomer at the same rate. Racemic vesicles undergo phase separation whereas homochiral systems continue to self-reproduce.
49. Menger FM, Gabrielson K: Chemically-induced birthing and foraging in vesicles systems. J Am Chem Soc 1994, 116:1567-1568.
50. Magome N, Takemura T, Yoshikawa K: Spontaneous formation for giant liposomes from neutral phospholipids. Chem Lett 1997, 205-206.
51. Menger FM, Lee SJ, Keiper JS: Differentiating unilamellar, multilamellar, and oligovesicular vesicles using a fluorescent dye. Langmuir 1996, 12:4479-4480.
52. 2+. Cation binding decreases head group area and induces fusion for the R,R/S,S pair whereas head group area and fission are observed for the R,S isomer.
53. Marchi-Artzner V, Jullien L, Gulik-Krzywicki T, Lehn J-M: Molecular recognition induced aggregation and fusion between vesicles containing lipids bearing complementary hydrogen bonding head-groups. Chem Commun 1997, 117-118. Vesicles of barbiturate and triaminopyrimidine lipids were stable by dynamic light scattering, but turbid aggregates formed for mixtures of vesicles. Electron microscopy showed dense collections of intact vesicles which evolved to contain very large vesicles.
54. Cornell BA, Braach-Maksvytis VLB, King LG, Osman PDJ, Raguse B, Wieczorek L, Pace RJ: A biosensor that uses ion-channel switches. Nature 1997, 387:580-583. The authors report on a tethered bilayer-based biosensor that contains a gramicidin channel as the current carrying component. The recognition event involves gramicidin-biotin conjugate, streptavidin, and an antibody for the biotinylated streptavidin. Current is regulated by disruptions of the gramicidin channel due to complex formation. This is a remarkable system which combines transport, aggregation control, membrane dynamics, and interfacial recognition to produce a macroscopic signal from molecular events.
55. Sackmann E: Supported membranes: scientific and practical applications. Science 1996, 271:43-48. An overview of the current strategies and challenges in the areas of supported membranes and phantom cells.