Interaction of the macrolide azithromycin with phospholipids. II. Biophysical and computer-aided conformational studies

European Journal of Pharmacology

Volumn 314, Issue 1-2, 1996, Pages 215-227

  Montenez, Jean Pierre ^a   Van Bambeke, Françoise ^a   Piret, Jocelyne ^a   Schanck, André ^a   Brasseur, Robert ^b   Tulkens, Paul M ^a   Mingeot Leclercq, Marie Paule ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^b UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

azithromycin; conformational analysis; fluorescence polarization; gentamicin; NMR spectroscopy, 31P; phospholipid

Indexed keywords

1,6 DIPHENYL 1,3,5 HEXATRIENE; AZITHROMYCIN; GENTAMICIN; LIPOSOME; MACROLIDE; PHOSPHATIDYLINOSITOL; PHOSPHOLIPID;

ARTICLE; COMPUTER; CONTROLLED STUDY; DRUG BINDING; DRUG CONFORMATION; ELECTRICITY; FLUORESCENCE POLARIZATION; HYDROPHILICITY; HYDROPHOBICITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; AZITHROMYCIN; COMPUTER SIMULATION; DRUG INTERACTIONS; FLUORESCENCE POLARIZATION; GENTAMICINS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PHOSPHOLIPIDS;

EID: 0030600520     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-2999(96)00553-5     Document Type: Article

References (53)

1. Bartlett, G.R., 1959, Phosphorus assay in column chromatography, J. Biol. Chem. 234, 466.
2. Brasseur, R., E. Goormaghtigh and J.M. Ruysschaert, 1981, Theoretical conformational analysis of phospholipid bilayers, Biochem. Biophys. Res. Commun. 103, 301.
3. Brasseur, R., M. Deleers, W.J. Malaisse and J.M. Ruysschaert, 1982, Conformational analysis of the calcium-A23182 complex at the lipid-water interface, Proc. Natl. Acad. Sci. USA 79, 2895.
4. Brasseur, R., G. Laurent, J.M. Ruysschaert and P.M. Tulkens, 1984, Interactions of aminoglycoside antibiotics with negatively-charged lipid layers: biochemical and conformational studies, Biochem. Pharmacol. 33, 629.
5. Brasseur, R., M. Deleers and J.M. Ruysschaert, 1986, Mode of organization of amphiphilic molecules at the lipid-water interface: a conformational analysis, J. Colloid. Interf. Sci. 114, 277.
6. Brasseur, R., B. Cornet, A. Burny, M. Vandenbranden and J.M. Ruysschaert, 1988a, Mode of insertion into lipid membrane of the N-terminus HIV gp 41 peptide segment, AIDS Res. Hum. Retrov. 4, 83.
7. Brasseur, R., P. Lorge, D, Espion, E. Goormaghtigh, A. Burny and J.M. Ruysschaert, 1988b, Mode of insertion into lipid matrix of the paramyxovirus F1 N-terminus, first step in host cell-virus fusion, Virus Genes 1, 325.
8. Brasseur, R., 1990, TAMMO: theoretical analysis of membrane molecular organization, in: Molecular Description of Biological Membrane Components by Computer-Aided Conformational Analysis, Vol. I/1.A.6., ed. R. Brasseur (CRC, Boca Raton) p. 203.
9. Brasseur, R., 1991, Differentiation of lipid-associating helices by use of three-dimensional molecular hydrophobicity potential calculations, J. Biol. Chem, 266, 16120.
10. Brasseur, R., L. Lins, B. Vanloo, J.M. Ruysschaert and M. Rosseneu, 1992, Molecular modelling of the amphipathic helices of the plasma apolipoproteins, Proteins 13, 246.
11. Bright, G.M., A.A. Nagel, J. Bordner, K.A. Desa, J.N. Dibrino, J. Nowakowska and F.C. Sciavolino, 1988, Synthesis, in vitro and in vivo activity of novel 9-deoxo-9a-AZA-9a-homoerythromycin A derivatives: a new class of macrolide antibiotics, the azalides, J. Antibiot. 12, 1029.
12. 31P nuclear magnetic resonance and freeze-fracture electron microscopy studies on Escherichia coli. I. Cytoplasmic membrane and total phospholipids, Biochim. Biophys. Acta 597, 492.
13. 31P-NMR lineshapes, Biochim. Biophys. Acta 603, 63.
14. Carlier, M.B., A. Zenebergh and P.M. Tulkens, 1987, Cellular uptake and subcellular distribution of roxithromycin and erythromycin in phagocytic cells, J. Antimicrob. Chemother. 20(B), 47.
15. Carlier, M.B., I. Garcia-Luque, J.P. Montenez, P.M. Tulkens and J. Piret, 1994, Accumulation, release and subcellular localization of azithromycin in phagocytic and non-phagocytic cells, Int. J. Tiss. React. 16, 211.
16. Chatelain, P., J. Ferreira, R. Laruel and J.M. Ruysschaert, 1986, Amiodarone induced modifications of the phospholipid physical state. A fluorescence polarization study, Biochem. Pharmacol. 35, 3007.
17. Chatelain, P. and R. Brasseur, 1990, Conformational analysis of cardiovascular drug-Hpid interactions: propanolol and amiodarone, in: Molecular Description of Biological Membranes by Computer Aided Conformational Analysis. Part 2. Mode of Insertion of Amphiphilic Components into the Lipid Membrane. Chapter 2.4., ed. R. Brasseur (CRC, Boca Raton) p. 43.
18. Davenport, L., R.E. Dale, R.H. Bisby and R.B. Cundall, 1985, Transverse location of the fluorescent probe 1,6-diphenyl-1,3,5-hexatriene in model lipid bilayer membrane systems by resonance excitation energy transfer, Biochemistry (USA) 24, 4097.
19. De Duve, C., T. De Barsy, B. Poole, A. Trauet, P.M. Tulkens and F. Van Hoof, 1974, Lysosomotropic agents, Biochem. Pharmacol. 23, 2495.
20. 31P-NMR and freeze-fracture electron microscopy, Biochim. Biophys. Acta 555, 200.
21. De Loof, H., S.C. Harvey, J.P. Segrest and R.W. Portor, 1991, Mean field stochastic boundary molecular dynamic simulation of a phospholipid in a membrane, Biochemistry 30, 2099.
22. Djokic, S., G. Kobrehel and G. Lazarevski, 1987, Erythromycin series. XII. Antibacterial in vitro evaluation of 10-dihydro-deoxo-11-azaerythromycin A: synthesis and structure-activity relationship of its acyl derivatives, J. Antibiot. 11, 1006.
23. Djokic, S., G. Kobrehel, N. Lopotar, B. Kamenar, A. Nagl and D. Mrvos, 1988. Erythromycin series. Part 13. Synthesis and structure elucidation of 10-dihydro-10-deoxo-11-methyl-11-azaerythromycin A, J. Chem. Res. (Summary) 152; (Manuscript) 1239.
24. Ferrer-Montiel, A.V., J.M. Gonzales-Ros and J.A. Ferragut, 1988, Association of daumomycin to membrane domains studied by fluorescence energy transfer, Biochim. Biophys. Acta 937, 379.
25. Foulds, G., R.M. Shepard and R.B. Johnson, 1990, The pharmacokinetics of azithromycin in human serum and tissues, J. Antimicrob. Chemother, 25(A), 73.
26. Gladue, R.P. and M.E. Snider, 1990, Intracellular accumulation of azithromycin by cultured human fibroblasts. Antimicrob. Agents Chemother. 34, 1056.
27. Gutiérrez-Merino, C., A. Molina, B. Escudero, A. Diez and J. Laynez, 1989, Interaction of the local anesthetics dibucaine and tetracaine with sarcoplasmic reticulum membranes. Differential scanning calorimetry and fluorescence studies, Biochemistry (USA) 28, 3398.
28. Hopfinger, A.J., 1973, in: Conformational Properties of Macromolecules, eds. B. Horecker, N.O. Kaplan, J. Marmur and H.A. Scheraga (Academic Press, New York).
29. Kirst, H.A. and G.D. Sides, 1989, New directions for macrolide antibiotics: structural modifications and in vitro activity, Antimicrob. Agents Chemother. 33, 1413.
30. Kitagawa, S., M. Matsubayashi, K. Kotani, K. Usui, K. and F. Kametani, 1991, Asymetry of membrane fluidity in the lipid bilayer of blood platelets: fluorescence study with diphenylhexatriene and analogs, J. Membr. Biol. 119, 221.
31. Martin, J.R., P. Johnson and M.F. Miller, 1985, Uptake, accumulation and egress of erythromycin by tissue culture cells of human origin, Antimicrob. Agents Chemother. 27, 314.
32. McCammon, J.A. and S.C. Harvey, 1987, in: Dynamics of Proteins and Nucleic Acids (Cambridge University Press, Cambridge).
33. 31P-NMR to model and biological membrane systems, FEBS Lett., 57, 213.
34. Mingeot-Leclercq, M.P., G. Laurent and P.M. Tulkens, 1988, Biochemical mechanism of aminoglycoside-induced inhibition of phosphatidylcholine hydrolysis by lysosomal phospholipases, Biochem. Pharmacol., 37, 591.
35. Mingeot-Leclercq, M.P., A. Schanck, M.F. Ronveaux-Dupal, M. Deleers, R. Brasseur, J.M. Ruysschaert and P.M. Tulkens, 1989, Ultrastructural, physico-chemical and conformational study of the interactions of gentamicin and bis(beta-diethylaminoethylether)hexestrol with negatively charged phospholipid bilayers, Biochem. Pharmacol., 38, 729.
36. Mingeot-Leclercq, M.-P., R. Brasseur and A. Schanck, 1995a, Molecular parameters involved in aminoglycosides nephrotoxicity, J. Toxicol. Environ. Health 44, 263.
37. Mingeot-Leclercq, M.-P., A. Schanck, F. Van Bambeke, P.M. Tulkens, L. Lins and R. Brasseur, 1995b, Molecular description of the interactions of aminoglycoside antibiotics with negatively-charged phospholipids. Theoretical molecular modelling and experimental results, Life Sci./Adv. Pharmacol. 14, 71.
38. Montenez, J.P., 1996: Etude des surcharges lysosomiales induites par l'azithromycine dans des cellules en culture: effets sur les phospholipides et le cholestérol cellulaires, in: Thesis (Université Catholique de Louvain, Bruxelles, Belgium) 185 pp.
39. Mouritsen, O.G. and K. Jorgensen, 1994, Dynamical order and disorder in lipid bilayers, Chem. Phys. Lipids 73, 3.
40. Piret, J., 1993, In vitro models for the study of the regulation of the activity of lysosomal phospholipase A1 by membrane lipids and of its inhibition by aminoglycoside antibiotics, in: Thesis (Université Catholique de Louvain and International Institute of Cellular and Molecular Pathology) 217 pp.
41. 15N nuclear magnetic resonance study, Magn. Res. Chem., 30, 11.
42. 31P nuclear magnetic resonance and the head group structure of phospholipids in membranes, Biochem. Biophys. Acta 515, 105.
43. Sheldrick, G.M., B. Kojic-Prodic, Z. Banic, G. Kobrehel and N. Kujundzic, 1995, Structure of 9-deoxo-9a-N-[N′-(4-pyridyl)-carbamoyl]-9a-aza-9a-homoerythromycin A and conformational analysis of analogous 9a-aza 15-membered azalides in solide state, Acta Cryst. B51, 358.
44. Shepard, R.M., D.E. Amacher, M.A. Mullins, R.A. Ferraina, C.V. Higgins, A.B. Jakowski and W.B. Milisen, 1992, Mechanism of azithromycin tissue uptake and accumulation: subcellular localization of azithromycin in rat liver, in: First International Conference on the Macrolides, Azalides and Streptogramines (Santa Fé, NM) p. A217.
45. Traüble, H. and H. Eibl, 1974, Electrostatic effects on lipid phase transition: membrane structure and ionic environment, Proc. Natl. Acad. Sci. USA 71, 214.
46. Tulkens, P.M., M.-P. Mingeot-Leclercq, G. Laurent and R. Brasseur, 1990, Conformational and biochemical analysis of the interactions phospholipids-aminoglycoside antibiotics in relation with their toxicity, in: Molecular Description of Biological Membrane Components by Computer-Aided Conformational Analysis, Vol.II, ed. by R. Brasseur (CRC, Boca Raton) p. 63.
47. Van Bambeke, F., M.-P. Mingeot-Leclercq, A. Schanck, R. Brasseur and P.M. Tulkens, 1993, Alterations in membrane permeability induced by aminoglycoside antibiotics: studies on liposomes and cultured cells, Eur. J. Pharmacol. 247, 155.
48. Van Bambeke, F., P.M. Tulkens, R. Brasseur and M.-P. Mingeot-Leclercq, 1995, Aminoglycoside antibiotics induce aggregation but not fusion of negatively-charged liposomes, Eur. J. Pharmacol. 289, 321.
49. Van Bambeke, F., J.P. Montenez, J. Piret, P.M. Tulkens and M.-P. Mingeot-Leclercq, 1996a, Interaction of the macrolide azithromycin with phospholipids: I. Inhibition of lysosomal phospholipase A1, Eur. J. Pharmacol. 314, 203.
50. Van Bambeke, F., M.-P. Mingeot-Leclercq, R. Brasseur, P.M. Tulkens and A. Schanck, 1996b, Aminoglycoside antibiotics prevent the formation of non bilayer structures in negatively-charged membranes. Comparative studies using fusogenic [bis-(beta-diethylaminoethylether)hexestrol] and aggregating (spermine) agents, Chem. Phys. Lipids 79, 123.
51. Wilschut, J., N. Düzgünes and D. Papahadjopoulos, 1981, Calcium/magnesium specificity in membrane fusion: kinetics of aggregation and fusion of phosphatidylserine vesicles and the role of bilayer curvature. Biochemistry 20, 3126.
52. Weiner, S.J., P.A. Kollman, D.A. Case, U.C. Singh, C. Ghio, G. Alagona and P. Weiner, 1984, A new force field for molecular mechanical simulation of nucleic acids and proteins, Am. Chem. Soc. 106, 765.
53. Zicha, J., J. Kunes, K.H. Le Quan Sang and M.A. Devynck, 1993, Regulation of the dynamic properties of platelet plasma membrane by intracellular sodium ions, Life Sci. 52, 1559.