Roles of integral protein in membrane permeabilization by amphidinols

Biochimica et Biophysica Acta - Biomembranes

Volumn 1778, Issue 6, 2008, Pages 1453-1459

  Morsy, Nagy ^a   Konoki, Keiichi ^a   Houdai, Toshihiro ^a   Matsumori, Nobuaki ^a   Oishi, Tohru ^a   Murata, Michio ^a   Aimoto, Saburo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Amphidinol; Antifungal; Glycophorin A; Hemolysis

Indexed keywords

AMPHIDINOL 14; AMPHIDINOL 15; AMPHIDINOL 2; AMPHIDINOL 3; AMPHIDINOL 6; AMPHIDINOL 7; ANTIFUNGAL AGENT; DODECYL SULFATE SODIUM; FLUORESCENT DYE; GLYCOPHORIN A; LIPOSOME;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BINDING AFFINITY; CHEMICAL MODEL; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG PROTEIN BINDING; HEMOLYSIS; HUMAN; HUMAN CELL; MEMBRANE PERMEABILITY; NONHUMAN; PHOSPHOLIPID MEMBRANE; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN DOMAIN; SURFACE PLASMON RESONANCE;

ALKENES; ANIMALS; ANTIFUNGAL AGENTS; CELL MEMBRANE PERMEABILITY; DINOFLAGELLIDA; ERYTHROCYTE MEMBRANE; GLYCOPHORIN; HUMANS; LIPID BILAYERS; LIPOSOMES; PYRANS; SURFACE PLASMON RESONANCE;

DINOPHYCEAE;

EID: 43649108461     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2008.01.018     Document Type: Article

References (30)

1. Satake M., Murata M., Yasumoto T., Fujita T., and Naoki H. Amphidinol, a polyhydroxypolyene antifungal agent with an unprecedented structure, from a marine dinoflagellate, Amphidinium klebsii. J. Am. Chem. Soc. 113 (1991) 9859-9861
2. Echigoya R., Rhodes L., Oshima Y., and Satake M. The structure of five new antifungal and hemolytic amphidinol analogs from Amphidinium carterae collected in New Zealand. Harmful Algae 4 (2005) 383-389
3. Paul G.K., Matsumori N., Murata M., and Tachibana K. Isolation and chemical structure of amphidinol-2, a potent hemolytic compound from marine dinoflagellate Amphidinium klebsii. Tetrahedron Lett. 36 (1995) 6279-6282
4. Morsy N., Matsuoka S., Houdai T., Matsumori N., Adachi S., Murata M., Iwashita T., and Fujita T. Isolation and structure elucidation of a new amphidinol with a truncated polyhydroxyl chain from Amphidinium klebsii. Tetrahedron 61 (2005) 8606-8610
5. Doi Y., Ishibashi M., Nakamichi H., Kosaka T., Ishikawa T., and Kobayashi J. Luteophanol A, a new polyhydroxyl compound from symbiotic marine dinoflagellate Amphidinium sp. J. Org. Chem. 62 (1997) 3820-3823
6. Huang X.H., Zhao D., Guo Y.W., Wu H.M., Lin L.P., Wang Z.H., DIng H., and Lin Y.S. Lingshuiol, a novel polyhydroxyl compound with strongly cytotoxic activity from the marine dinoflagellate Amphidinium sp. Bioorg. Med. Chem. 14 (2004) 3117-3120
7. Washida K., Koyama T., Yamada K., Kita M., and Uemura D. Karatungiols A and B, two novel antimicrobial polyol compounds, from the symbiotic marine dinoflagellate Amphidinium sp. Tetrahedron Lett. 47 (2006) 2521-2525
8. Houdai T., Matsuoka S., Morsy N., Matsumori N., Satake M., and Murata M. Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities. Tetrahedron 61 (2005) 2795-2802
9. Houdai T., Matsuoka S., Matsumori N., and Murata M. Membrane-permeabilizing activities of amphidinol 3, polyene-polyhydroxy antifungal from a marine dinoflagellate. Biochim. Biophys. Acta 1667 (2004) 91-100
10. Morsy N., Houdai T., Matsuoka S., Matsumori N., Adachi S., Oishi T., Murata M., Iwashita T., and Fujita T. Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities. Bioorg. Med. Chem. 14 (2006) 6548-6554
11. Paul G.K., Matsumori N., Konoki K., Murata M., and Tachibana K. Chemical structures of amphidinols 5 and 6 isolated from marine dinoflagellate Amphidinium klebsii and their cholesterol-dependent membrane disruption. J. Mar. Biotech. 5 (1997) 124-128
12. Murata M., Matsuoka S., Matsumori N., Paul G.K., and Tachibana K. Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol homologues: application of a new configuration analysis based on carbon-hydrogen spin-coupling constants. J. Am. Chem. Soc. 121 (1999) 870-871
13. N. Morsy, T. Houdai, K. Konoki, N. Matsumori, T. Oishi, M. Murata, Effects of lipid constituents on membrane-permeabilizing activity of amphidinols, Bioorg. Med. Chem. (in press).
14. Tomita M., Furthmayr F., and Marchesi V.T. Primary structure of human erythrocyte glycophorin A. Isolation and characterization of peptides and complete amino acid sequence. Biochemistry 17 (1978) 4756-4770
15. Challou N., Goormaghtigh E., Cabiaux V., Conrath K., and Ruysschaert J. Sequence and structure of the membrane-associated peptide of glycophorin A. Biochemistry 33 (1994) 6902-6910
16. Bormann B.J., Knowles W.J., and Marchesi V.T. Synthetic peptides mimic the assembly of transmembrane glycoproteins. J. Biol. Chem. 264 (1989) 4033-4037
17. Cortajarena A.L., Goni F.M., and Ostolaza H. Glycophorin as a receptor for Escherichia coli alpha-hemolysin in erythrocytes. J. Biol. Chem. 276 (2001) 12513-12519
18. Howard S.P., and Buckley T. Membrane glycoprotein receptor and hole-forming properties of a cytolytic protein toxin. Biochemistry 21 (1982) 1662-1667
19. Garland W.J., and Buckley T. The cytolytic toxin aerolysin must aggregate to disrupt erythrocytes, and aggregation is stimulated by human glycophorin. Infect. Immun. 56 (1988) 1249-1253
20. Houdai T., Matsuoka S., Murata M., Satake M., Ota S., Oshima Y., and Rhodes L.L. Acetate labeling patterns of dinoflagellate polyketides, amphidinols 2, 3 and 4. Tetrahedron 57 (2001) 5551-5555
21. Smith S.O., Song D., Shekar S., Groesbeek M., Ziliox M., and Aimoto S. Structure of the transmembrane dimer interface of glycophorin A in membrane bilayers. Biochemistry 40 (2001) 6553-6558
22. Takayama M., Itoh S., Nagasaki T., and Tanimizu I. A new enzymatic method for determination of serum choline-containing phospholipids. Clin. Chim. Acta 79 (1977) 93-98
23. MacDonald R.I., and MacDonald R.C. Assembly of phospholipid vesicles bearing sialoglycoprotein from erythrocyte membrane. J. Biol. Chem. 250 (1988) 9206-9214
24. Springer G.F., Nagai Y., and Tegtmeyer H. Isolation and properties of human blood-group NN and meconium-Vg antigens. Biochemistry 5 (1966) 3254-3272
25. Adair B.D., and Engelman D.M. Glycophorin A helical transmembrane domains dimerize in phospholipid bilayers: a resonance energy transfer study. Biochemistry 33 (1994) 5539-5544
26. Mackenzie K.R., Prestegard J.H., and Engelman D.M. A transmembrane helix dimer: structure and implications. Science 276 (1997) 131-133
27. Mori M., Oishi T., Matsuoka S., Ujihara S., Matsumori N., Murata M., Satake M., Oshima Y., Matsushita N., and Aimoto S. Ladder-shaped polyether compound, desulfated yessotoxin, interacts with membrane-integral alpha-helix peptides. Bioorg. Med. Chem. 13 (2005) 5099-5103
28. Torikai K., Yari H., Mori M., Ujihara S., Matsumori N., Murata M., and Oishi T. Design and synthesis of an artificial ladder-shaped polyether that interacts with glycophorin A. Bioorg. Med. Chem. Lett. 16 (2006) 6355-6359
29. Chasis J.A., and Mohandas N. Red blood cell glycophorin. Blood 80 (1992) 1869-1879
30. Zhang D., Takahashi J., Seno T., Tani Y., and Honda T. Analysis of receptor for Vibrio cholerae El tor hemolysin with a monoclonal antibody that recognizes glycophorin B of human erythrocyte membrane. Infect. Immun. 67 (1999) 5332-5337