A tailoring activity is responsible for generating polyene amide derivatives in Streptomyces diastaticus var. 108

Chemistry and Biology

Volumn 12, Issue 10, 2005, Pages 1093-1101

  Seco, Elena M ^a   Fotso, Serge ^b   Laatsch, Hartmut ^b   Malpartida, Francisco ^a  

^a CENTRO NACIONAL DE BIOTECNOLOGÍA   (Spain)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

STREPTOMYCES; STREPTOMYCES DIASTATICUS;

EID: 26944451317     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2005.08.007     Document Type: Article

References (32)

1. M. Baginski, H. Resat, and E. Borowski Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels Biochim. Biophys. Acta 1567 2002 63 78
2. B.E. Cohen Amphotericin B toxicity and lethality: a tale of two channels Int. J. Pharm. 162 1998 95 106
3. B.E. Cohen, H. Ramos, M. Gamargo, and J. Urbina The water and ionic permeability induced by polyene antibiotics across plasma membrane vesicles from Leishmania sp Biochim. Biophys. Acta 860 1986 57 65
4. A.K. Saha, T. Mukherjee, and A. Bhaduri Mechanism of action of amphotericin B on Leishmania donovani promastigotes Mol. Biochem. Parasitol. 19 1986 195 200
5. K.T. Adjou, R. Demaimay, J.P. Deslys, C.I. Lasmezas, V. Beringue, S. Demart, F. Lamoury, M. Seman, and D. Dormont MS-8209, a water-soluble amphotericin B derivative, affects both scrapie agent replication and PrPres accumulation in Syrian hamster scrapie J. Gen. Virol. 80 1999 1079 1085
6. M. Chéron, B. Cybulska, J. Mazerski, J. Grzybowska, A. Czerwinski, and E. Borowski Quantitative structure-activity relationships in amphotericin B derivatives Biochem. Pharmacol. 37 1988 827 836
7. B. Cybulska, J. Bolard, O. Seksek, A. Czerwinski, and E. Borowski Identification of the structural elements of amphotericin B and other polyene macrolide antibiotics of the hepteane group influencing the ionic selectivity of the permeability pathways formed in the red cell membrane Biochim. Biophys. Acta 1240 1995 167 178
8. B. Cybulska, I. Gadomska, J. Mazerski, J.G.E. Borowski, M. Cheron, and J. Bolard N-Methyl-N-D-fructosyl amphotericin B methyl ester (MF-AME), a novel antifungal agent of low toxicity: monomer/micelle control over selective toxicity Acta Biochim. Pol. 47 2000 121 131
9. J.R. Graybill, L.K. Najvar, A. Fothergill, T. Hardin, M. Rinaldi, C. Lambros, and S.L. Regen KY-62, a polyene analog of amphotericin B, for treatment of murine candidiasis Antimicrob. Agents Chemother. 42 1998 147 150
10. J. Mazerski, J. Bolard, and E. Borowski Effect of the modifications of ionizable groups of amphotericin B on its ability to form complexes with sterols in hydroalcoholic media Biochim. Biophys. Acta 1236 1995 170 176
11. R.M. Parmegiani, D. Loebenberg, B. Antonacci, T. Yarosh-Tomaine, R. Scupp, J.J. Wright, P.J. Chiu, and G.H. Miller Comparative in vitro and in vivo evaluation of N-D-ornithyl amphotericin B methyl ester, amphotericin B methyl ester, and amphotericin B Antimicrob. Agents Chemother. 31 1987 1756 1760
12. J. Szlinder-Richert, J. Mazerski, B. Cybulska, J. Grzybowska, and E. Borowski MFAME, N-methyl-N-D-fructosyl amphotericin B methyl ester, a new amphotericin B derivative of low toxicity: relationship between self-association and effects on red blood cells Biochim. Biophys. Acta 1528 2001 15 24
13. F.J. Pérez-Zúñiga, E.M. Seco, T. Cuesta, F. Degenhardt, J. Rohr, C. Vallín, Y. Iznaga, M.E. Pérez, L. González, and F. Malpartida CE-108, a new macrolide tetraene antibiotic J. Antibiot. (Tokyo) 57 2004 197 204
14. E.M. Seco, T. Cuesta, S. Fotso, H. Laatsch, and F. Malpartida Two polyene amides produced by genetically modified Streptomyces diastaticus var. 108 Chem. Biol. 12 2005 535 543
15. H. Petkovic, A. Thamchaipenet, L.H. Zhou, D. Hranueli, P. Raspor, P.G. Waterman, and I.S. Hunter Disruption of an aromatase/cyclase from the oxytetracycline gene cluster of Streptomyces rimosus results in production of novel polyketides with shorter chain lengths J. Biol. Chem. 274 1999 32829 32834
16. E.M. Seco, F.J. Pérez-Zuñiga, M.S. Rolón, and F. Malpartida Starter unit choice determines the production of two tetraene macrolides, rimocidin and CE-108, in Streptomyces diastaticus var. 108 Chem. Biol. 11 2004 357 366
17. S. Chen, X. Huang, X. Zhou, L. Bai, J. He, K.J. Jeong, S.Y. Lee, and Z. Deng Organizational and mutational analysis of a complete FR-008/candicidin gene cluster encoding a structurally related polyene complex Chem. Biol. 10 2003 1065 1076
18. L.M. Cañedo, L. Costa, L.M. Criado, J.L. Fernández Puentes, and M.A. Moreno AB-400, a new tetraene macrolide isolated from Streptomyces costae J. Antibiot. (Tokyo) 53 2000 623 626
19. E. Borowski Novel approaches in the rational design of antifungal agents of low toxicity Farmaco 55 2000 206 208
20. T. Brautaset, P. Bruheim, H. Sletta, L. Hagen, T.E. Ellingsen, A.R. Strom, S. Valla, and S.B. Zotchev Hexaene derivatives of nystatin produced as a result of an induced rearrangement within the nysC polyketide synthase gene in S. noursei ATCC 11455 Chem. Biol. 9 2002 367 373
21. B. Byrne, M. Carmody, E. Gibson, B. Rawlings, and P. Caffrey Biosynthesis of deoxyamphotericins and deoxyamphoteronolides by engineered strains of Streptomyces nodosus Chem. Biol. 10 2003 1215 1224
22. M.V. Mendes, E. Recio, R. Fouces, R. Luiten, J.F. Martin, and J.F. Aparicio Engineered biosynthesis of novel polyenes: a pimaricin derivative produced by targeted gene disruption in Streptomyces natalensis Chem. Biol. 8 2001 635 644
23. J.F. Aparicio, P. Caffrey, J.A. Gil, and S.B. Zotchev Polyene antibiotic biosynthesis gene clusters Appl. Microbiol. Biotechnol. 61 2003 179 188
24. P. Caffrey, S. Lynch, E. Flood, S. Finnan, and M. Oliynyk Amphotericin biosynthesis in Streptomyces nodosus: deductions from analysis of polyketide synthase and late genes Chem. Biol. 8 2001 713 723
25. E. Fjaervik, and S.B. Zotchev Biosynthesis of the polyene macrolide antibiotic nystatin in Streptomyces noursei Appl. Microbiol. Biotechnol. 67 2005 436 443
26. M. Carmody, B. Murphy, B. Byrne, P. Power, D. Rai, B. Rawlings, and P. Caffrey Biosynthesis of amphotericin derivatives lacking exocyclic carboxyl groups J. Biol. Chem. 2005 in press. Published online August 3, 2005. 10.1074/jbc.M506689200
27. R.M. Atlas Microbiological Media 1993 CRC Press Boca Raton, FL
28. T. Kieser, M.J. Bibb, M.J. Buttner, K.F. Chater, and D.A. Hopwood Practical Streptomyces Genetics 2000 John Innes Foundation Norwich, UK
29. T. Maniatis, E.F. Fritsch, and J. Sambrook Molecular Cloning: A Laboratory Manual 1982 Cold Spring Harbor Laboratory Press Cold Spring Harbor, NY
30. C. Yanisch-Perron, J. Vieira, and J. Messing Improved M13 phage cloning vectors and host strains: nucleotide sequences of the M13mp18 and pUC19 vectors Gene 33 1985 103 119
31. J.L. Larson, and C.L. Hershberger The minimal replicon of a streptomycete plasmid produces an ultrahigh level of plasmid DNA Plasmid 15 1986 199 209
32. F. Malpartida, and D.A. Hopwood Physical and genetic characterisation of the gene cluster for the antibiotic actinorhodin in Streptomyces coelicolor A3(2) Mol. Gen. Genet. 205 1986 66 73