Lipid binding and membrane penetration of polymyxin B derivatives studied in a biomimetic vesicle system

Biochemical Journal

Volumn 375, Issue 2, 2003, Pages 405-413

  Katz, Marina ^a   Tsubery, Haim ^b   Kolusheva, Sofiya ^a   Shames, Alex ^a   Fridkin, Mati ^b   Jelinek, Raz ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Antibacterial peptides; Fluorescence quenching; Membranes; Polydiacetylene; Polymyxin B

Indexed keywords

BACTERIA; CELL MEMBRANES; ELECTRON SPIN RESONANCE SPECTROSCOPY; FLUORESCENCE; LIPIDS; POLYPEPTIDES; QUENCHING;

MEMBRANE ASSOCIATION;

BIOCHEMISTRY;

ALKYL GROUP; AMINO ACID; ANTIBIOTIC AGENT; CYCLOPEPTIDE; LIPOPOLYSACCHARIDE; POLYMYXIN B;

ANTIBACTERIAL ACTIVITY; ARTICLE; BIOMIMETICS; CALORIMETRY; CELL MEMBRANE PERMEABILITY; CYCLIZATION; DIASTEREOISOMER; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG TRANSPORT; ELECTRON SPIN RESONANCE; FLUORESCENCE; HYDROPHOBICITY; LIPID VESICLE; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE;

BINDING, COMPETITIVE; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROPHOBICITY; LIPID BILAYERS; LIPIDS; LIPOPOLYSACCHARIDES; MOLECULAR STRUCTURE; POLYMYXIN B; SPECTROMETRY, FLUORESCENCE;

BACTERIA (MICROORGANISMS); INSERTION SEQUENCES; NEGIBACTERIA;

EID: 0142169531     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20030784     Document Type: Article

References (38)

1. Nikaido, H. and Vaara, M. (1987) Outer membrane. In Escherichia coli and Salmonella typhimurium (Neidhardt, F. C., ed.), pp. 7-22, American Society for Microbiology, Washington, DC
2. Cronan, J. E., Gennis, R. B. and Maloy, S. M. (1987) Cytoplasmic Membrane. In Escherichia coli and Salmonella typhimurium (Neidhardt, F. C., ed.), pp. 31-55, American Society for Microbiology, Washington, DC
3. Brandenburg, K., Kusumoto, S. and Seydel, U. (1997) Conformational studies of synthetic lipid A analogs and partial structures by infrared spectroscopy. Biochem. Biophys. Acta 1329, 183-201
4. Snyder, S., Kim, D. and McIntosh T. J. (1999) Lipopolysaccharide bilayer structure: effect of chemotype, core mutations, divalent cations, and temperature. Biochemistry 38, 10758-10767
5. Danner, R. L., Joiner, K. A., Rubin M., Patterson, W. H., Johnson, N., Ayers, K. M. and Parrillo, J. E. (1989) Purification, toxicity, and antiendotoxin activity of polymyxin B nonapeptide. Antimicrob. Agents Chemother. 33, 1428-1434
6. Moore, R. A., Bates, N. C. and Hancock, R. E. (1986) Interaction of polycationic antibiotics with Pseudomonas aeruginosa lipopolysaccharide and lipid A studied by using dansyl-polymyxin. Antimicrob. Agents Chemother. 9, 496-500
7. Chihara, S., Ito, A., Yahata, M., Tobita, T. and Koyama, Y. (1973) Colistin nonapeptide derivatives. I. Chemical synthesis and characterization of α-N-octanoyl and other α-N-acyl colistin nonapeptide derivatives. Agric. Biol. Chem. 37, 2709
8. Chihara, S., Ito, A., Yahata, M., Tobita, T. and Koyama, Y. (1974) Colistin nonapeptide derivatives. II. Chemical synthesis, isolation, and characterization of α-N-fattyacyl colistin nonapeptide with special reference to the correlation between antimicrobial activity and carbon number of fattyacyl moiety. Agric. Biol. Chem. 38, 521-529
9. Duwe, A. K., Rupar, C. A., Horsman, G. B. and Vas, S. I. (1986) In vitro cytotoxicity and antibiotic activity of polymyxin B nonapeptide. Antimicrob, Agents Chemother. 30, 340-341
10. Chihara, S., Ito, A., Yahata, M., Tobita, T. and Koyama, Y. (1973) Enzymatic degradation of colistin. Isolation and identification of α-N-acyl α,γ-diaminobutyric acid and colistin nonapeptide. Agric. Biol. Chem. 37, 2455-2463
11. Vaara, M. and Vaara, T. (1983) Sensitization of Gram-negative bacteria to antibiotics and complement by a nontoxic oligopeptide. Nature (London) 303, 526-528
12. Tsubery, H., Ofek, I., Cohen, S. and Fridkin, M. (2000) Structure-function studies of polymyxin B nonapeptide: implications to sensitization of gram-negative bacteria. J. Med. Chem. 43, 3085-3092
13. Tsubery, H., Ofek, I., Cohen, S. and Fridkin, M. (2000) The functional association of polymyxin B with bacterial lipopolysaccharide is stereospecific: studies on polymyxin B nonapeptide. Biochemistry 39, 11837-11844
14. Tsubery, H., Ofek, I., Cohen, S. and Fridkin, M. (2001) N-terminal modifications of polymyxin B nonapeptide and their effect on antibacterial activity Peptides 22, 1675-1681
15. Kolusheva, S., Shahal, T. and Jelinek, R. (2000) Peptide-membrane interactions studied by a new phospholipid/polydiacetylene colorimetric vesicle assay. Biochemistry 39, 15851-15859
16. Kolusheva, S., Boyer, L. and Jelinek, R. (2000) A colorimetric assay for rapid screening of antimicrobial peptides. Nat. Biotechnol. 18, 225-227
17. Kolusheva, S., Kafri, R., Katz, M. and Jelinek, R. (2001) Rapid colorimetric detection of antibody-epitope recognition at a biomimetic membrane interface. J. Am. Chem. Soc. 123, 417-422
18. Evrard, D., Touitou, E., Kolusheva, S., Fishov, Y. and Jelinek, R. (2001) A new colorimetric assay for studying and rapid screening of membrane penetration enhancers. Pharm. Res. 18, 943-949
19. Gaboriaud, F., Golan, R., Volinsky, R., Berman, A. and Jelinek, R. (2001) Organization and structural properties of Langmuir films composed of conjugated polydiacetylene and phospholipids. Langmuir 17, 3651-3657
20. Volinsky, R., Gaboriaud, F., Berman, A. and Jelinek R. (2002) Morphology and organization of phospholipid/diacetylene Langmuir films studied by Brewster angle microscopy and fluorescence microscopy. J. Phys. Chem. 106, 9231-9236
21. Kolusheva, S., Wachtel, E. and Jelinek, R. (2003) Biomimetic lipid/polymer colorimetric membranes: molecular and cooperative properties. J. Lipid Res. 44, 65-71
22. Satchell, D. P., Sheynis, T., Shirafuji, Y., Kolusheva, S., Ouellette, A. and Jelinek, R. (2003) Interactions of mouse paneth cell α-defensins with membranes studied by a biomimetic lipid/polymer colorimetric assay. J. Biol. Chem, 278, 13838-13847
23. Lowry, O. H., Rosebrough, N. J., Farr, A. L. and Randall, R. J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275
24. Okada, S., Peng, S., Spevak, W. and Charych, D. (1998) Color and chromism of polydiacetylene vesicles. Acc. Chem. Res. 31, 229-239
25. Vaara, M. and Viljanen, P. (1985) Binding of polymyxin B nonapeptide to Gram-negative Bacteria. Antimicrob. Agents Chemother. 27, 548-554
26. Ofek, J., Cohen, S., Rahmani, R., Kabha, K., Tamarkin, D., Herzig, Y and Rubinstein, E. (1994) Antibacterial synergism of polymyxin B nonapeptide and hydrophobic antibiotics in experimental gram-negative infections in mice. Antimicrob. Agents Chemother. 38, 374-377
27. Li, C., Budge, L. P., Driscoll, C. D., Willardson, B. M., Allman, G. W., and Savage, P. B. (1999) Incremental conversion of outer-membrane permeabilizers into potent antibiotics for Gram-negative Bacteria. J. Am. Chem, Soc. 121, 931-940
28. Ringsdorf, H., Schlarb, B. and Venzmer, J. (1988) Molecular architecture and function of polymeric oriented systems: models for the study of organization, surface recognition, and dynamics of biomembranes, Angew. Chem. Int. Edn. Engl. 27, 113-158
29. Charych, D. H., Nagy, J. O., Spevak, W. and Bednarsky, M. D. (1993) Direct colorimetric detection of a receptor-ligand interaction by a polymerized bilayer assembly. Science 261, 585-588
30. Latorre, R. and Alvarez, O. (1981) Voltage-dependent channels in planar lipid bilayer membranes. Physiol. Rev. 61, 77-150
31. Fidai, S., Farmer, S. W. and Hancock, R. E. W. (1997) Interaction of cationic peptides with bacterial membranes. Methods Mol. Biol. 78, 187-204
32. Oren, Z. and Shai, Y. (1997) Selective lysis of bacteria but not mammalian cells by diastereomers of melittin: structure-function study. Biochemistry 36, 1826-1835
33. Chattopadhyay, A. and London, E. (1987) Parallax method for direct measurement of membrane penetration depth utilizing fluorescence quenching by spin-labeled phospholipids. Biochemistry 26, 39-45
34. McIntyre, J. C. and Sleight, R. G. (1991) Fluorescence assay for phospholipid membrane asymmetry. Biochemistry 30, 11819-11827
35. 2. Biochemistry 36, 3870-3881
36. Marsh, D. (1981) Membrane Spectroscopy, Springer-Verlag, Berlin
37. Kleinschmidt, J. H., Mahaney, J. E., Thomas, D. D. and Marsh, D. (1997) Interaction of bee venom melittin with zwitterionic and negatively charged phospholipid bilayers: a spin-label electron spin resonance study. Biophys. J. 72, 767-778
38. Tsubery, H., Ofek, I., Cohen, S., Eisenstein, M. and Fridkin, M. (2002) Modulation of the hydrophobic domain of polymyxin B nonapeptide: effect on outer-membrane permeabilization and lipopolysaccharide neutralization. Mol. Pharm. 62, 1036-1042