Thiazinogeldanamycin, a new geldanamycin derivative produced by Streptomyces hygroscopicus 17997

Journal of Microbiology and Biotechnology

Volumn 21, Issue 6, 2011, Pages 599-603

  Ni, Siyang ^a   Wu, Linzhuan ^a   Wang, Hongyuan ^a   Gan, Maoluo ^a   Wang, Yucheng ^a   He, Weiqing ^a   Wang, Yiguang ^a  

^a BEIJING HOSPITAL   (China)

Author keywords

Streptomyces hygroscopicus 17997; Thiazinogeldanamycin

Indexed keywords

GELDANAMYCIN; THIAZINOGELDANAMYCIN; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL STRAIN; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG PURIFICATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; FERMENTATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES HYGROSCOPICUS; STREPTOMYCES HYGROSCOPICUS 17997;

BENZOQUINONES; BIOTECHNOLOGY; CELL LINE, TUMOR; CHROMATOGRAPHY, LIQUID; CULTURE MEDIA; CYSTEINE; HUMANS; LACTAMS, MACROCYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; STREPTOMYCES;

STREPTOMYCES HYGROSCOPICUS;

EID: 79960003777     PISSN: 10177825     EISSN: 17388872     Source Type: Journal    
DOI: 10.4014/jmb.1011.11006     Document Type: Article

References (17)

1. Charifson, P. S., J. J. Corkery, M. A. Murcko, and W. P. Walters. 1999. Consensus scoring: A method for obtaining improved hit rates from docking databases of three-dimensional structures into proteins. J. Med. Chem. 42: 5100-5109.
2. Cricchio, R., P. Antonini, and G. Sartori. 1980. Thiazorifamycins. III. Biosynthesis of rifamycins P, Q and verde, novel metabolites from a mutant of Nocardia mediterranea. J. Antibiot. (Tokyo) 33: 842-846.
3. DeBoer, C., P. A. Meulman, R. J. Wnuk, and D. H. Peterson. 1970. Geldanamycin, a new antibiotic. J. Antibiot. (Tokyo) 23: 442-447.
4. Ge, J., E. Normant, J. R. Porter, J. A. Ali, M. S. Dembski, Y. Gao, et al. 2006. Design, synthesis, and biological evaluation of hydroquinone derivatives of 17-amino-17-demethoxygeldanamycin as potent, water-soluble inhibitors of Hsp90. J. Med. Chem. 49: 4606-4615.
5. Hong, Y. S., D. Lee, W. Kim, J. K. Jeong, C. G. Kim, J. K. Sohng, J. H. Lee, S. G. Paik, and J. J. Lee. 2004. Inactivation of the carbamoyltransferase gene refines post-polyketide synthase modification steps in the biosynthesis of the antitumor agent geldanamycin. J. Am. Chem. Soc. 126: 11142-11143.
6. Hosokawa, N., H. Naganawa, H. Inuma, M. Hamada, T. Takeuchi, T. Kanbe, and M. Hori. 1995. Thiazinotrienomycins, new ansamycin group antibiotics. J. Antibiot. (Tokyo) 48: 471-478.
7. Lang, W., G. W. Caldwell, J. Li, G. C. Leo, W. J. Jones, and J. A. Masucci. 2007. Biotransformation of geldanamycin and 17-allylamino-17-demethoxygeldanamycin by human liver microsomes: Reductive versus oxidative metabolism and implications. Drug Metab. Dispos. 35: 21-29.
8. Le Brazidec, J. Y., A. Kamal, D. Busch, L. Thao, L. Zhang, G. Timony, et al. 2004. Synthesis and biological evaluation of a new class of geldanamycin derivatives as potent inhibitors of Hsp90. J. Med. Chem. 47: 3865-3873.
9. Liu, A. M., L. Z. Wu, Y. G. Wang, H. T. Zhang, W. Q. He, Y. H. Li, and K. Zhang. 2008. A color reaction method for early preliminary discrimination of benzenic ansamycins [In Chinese]. Chin. J. Antibiot. 33: 403-406.
10. Nishio, M., J. Kohno, M. Sakurai, S. I. Suzuki, N. Okada, K. Kawano, and S. Komatsubara. 2000. TMC-135A and B, new triene-ansamycins, produced by Streptomyces sp. J. Antibiot. (Tokyo) 53: 724-727.
11. Rascher, A., Z. Hu, G. O. Buchanan, R. Reid, and C. R. Hutchinson. 2005. Insights into the biosynthesis of the benzoquinone ansamycins geldanamycin and herbimycin, obtained by gene sequencing and disruption. 2005. Appl. Environ. Microbiol. 71: 4862-4871.
12. Roe, S. M., C. Prodromou, R. O'Brien, J. E. Ladbury, P. W. Piper, and L. H. Pearl. 1999. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. J. Med. Chem. 42: 260-266.
13. Schnur, R. C., M. L. Corman, R. J. Gallaschun, B. A. Cooper, M. F. Dee, J. L. Doty, et al. 1995. Inhibition of the oncogene product p185erbB-2 in vitro and in vivo by geldanamycin and dihydrogeldanamycin derivatives. J. Med. Chem. 38: 3806-3812.
14. Schnur, R. C., M. L. Corman, R. J. Gallaschun, B. A. Cooper, M. F. Dee, J. L. Doty, et al. 1995. erbB-2 oncogene inhibition by geldanamycin derivatives: Synthesis, mechanism of action, and structure-activity relationships. J. Med. Chem. 38: 3813-3820.
15. Shin, J. C., Z. Na, D. H. Lee, W. C. Kim, K. Lee, Y. M. Shen, S. G. Paik, Y. S. Hong, and J. J. Lee. 2008. Characterization of tailoring genes involved in the modification of geldanamycin polyketide in Streptomyces hygroscopicus JCM4427. J. Microbiol. Biotechnol. 18: 1101-1108.
16. Stebbins, C. E., A. A. Russo, C. Schneider, N. Rosen, F-U. Hartl, and N. P. Pavletich. 1997. Crystal structure of an Hsp90-geldanamycin complex: Targeting of a protein chaperone by an antitumor agent. Cell 89: 239-250.
17. Wanga, R., L. Laib, and S. Wanga. 2002. Further development and validation of empirical scoring functions for structure-based binding affinity prediction. J. Comput. Aided Mol. Des. 16: 11-26.