New non-quinone geldanamycin analogs from genetically engineered Streptomyces hygroscopicus

Journal of Antibiotics

Volumn 64, Issue 6, 2011, Pages 461-463

  Wu, Cheng Zhu ^a,b   Moon, An Na ^c   Jang, Jae Hyuk ^a   Lee, Dongho ^d   Kang, Sun Young ^a,e   Park, Joon Tae ^c   Ahn, Jong Seog ^a   Hwang, Bang Yeon ^e   Kim, Young Ho ^b   Lee, Hong Sub ^c   Hong, Young Soo ^a  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Chungnam National University   (South Korea)

^c Ildong Pharmaceutical Co   (South Korea)

^d Korea University   (South Korea)

^e Chungbuk National University   (South Korea)

Author keywords

biosynthetic engineering; geldanamycin; Hsp90 inhibitor; non quinone geldanamycin

Indexed keywords

DHQ 3; DHQ 7; DHQ 8; GELDANAMYCIN; GELDANAMYCIN DERIVATIVE; UNCLASSIFIED DRUG;

DRUG ACTIVITY; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; GENETIC ENGINEERING; NONHUMAN; NOTE; PRIORITY JOURNAL; STREPTOMYCES HYGROSCOPICUS;

ADENOSINE TRIPHOSPHATASES; ANTIBIOTICS, ANTINEOPLASTIC; BENZOQUINONES; CELL LINE, TUMOR; GENETIC ENGINEERING; HSP90 HEAT-SHOCK PROTEINS; HUMANS; LACTAMS, MACROCYCLIC; STREPTOMYCES;

STREPTOMYCES HYGROSCOPICUS;

EID: 79959736928     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2011.24     Document Type: Note

References (20)

1. Janin, Y. L. ATPase inhibitors of heat-shock protein 90, second season. Drug Discov. Today. 15, 342-353 (2010).
2. Whitesell, L. & Lindquist, S. L. HSP90 and the chaperoning of cancer. Nat. Rev. Cancer. 5, 761-772 (2005).
3. Prodromou, C. & Pearl, L. H. Structure and functional relationships of Hsp90. Curr. Cancer Drug Targets. 3, 301-323 (2003).
4. Bishop, S. C., Burlison, J. A. & Blagg, B. S. Hsp90: a novel target for the disruption of multiple signaling cascades. Curr. Cancer Drug Targets. 7, 369-388 (2007).
5. Kamal, A. et al. A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors. Nature 425, 407-410 (2003).
6. Neckers, L. & Lee, Y. S. Cancer: the rules of attraction. Nature 425, 357-359 (2003).
7. Whitesell, L., Mimnaugh, E. G., De Costa, B., Myers, C. E. & Neckers, L. M. Inhibition of heat shock protein HSP90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: essential role for stress proteins in oncogenic transformation. Proc. Natl Acad. Sci. USA. 91, 8324-8328 (1994).
8. Panaretou, B. et al. ATP binding and hydrolysis are essential to the function of the Hsp90molecular chaperone in vivo. EMBO J. 17, 4829-4836 (1998).
9. Supko, J. G., Hickman, R. L., Grever, M. R. & Malspeis, L. Preclinical pharmacologic evaluation of geldanamycin as an antitumor agent. Cancer Chemother. Pharmacol. 36, 305-315 (1995).
10. Taldone, T., Sun, W. & Chiosis, G. Discovery and development of heat shock protein 90 inhibitors. Bioorg. Med. Chem. 17, 2225-2235 (2009).
11. Neckers, L. & Neckers, K. Heat-shock protein 90 inhibitors as novel cancer chemotherapeutics - an update. Expert Opin. Emerg Drugs. 10, 137-149 (2005).
12. Heath, E. I. et al. A phase II trial of 17-allylamino-17- demethoxygeldanamycin in patients with hormone-refractory metastatic prostate cancer. Clin. Cancer Res. 14, 7940-7946 (2008).
13. Cysyk, R. L., Parker, R. J., Barchi, J. J. Jr., Steeg, P. S., Hartman, N. R. & Strong, J. M. Reaction of geldanamycin and C17-substituted analogues with glutathione: product identifications and pharmacological implications. Chem. Res. Toxicol. 19, 376-381 (2006).
14. Maroney, A. C. et al. Dihydroquinone ansamycins: toward resolving the conflict between low in vitro affinity and high cellular potency of geldanamycin derivatives. Biochemistry 45, 5678-5685 (2006).
15. Zhang, M. Q. et al. Optimizing natural products by biosynthetic engineering: discovery of nonquinone Hsp90 inhibitors. J. Med. Chem. 51, 5494-5497 (2008).
16. Kim, W. et al. Rational biosynthetic engineering for optimization of geldanamycin analogues. ChemBioChem. 10, 1243-1251 (2009).
17. Kim, W. et al. Mutasynthesis of geldanamycin by the disruption of a gene producing starter unit: generation of structural diversity at the benzoquinone ring. ChemBioChem. 8, 1491-1494 (2007).
18. Hong, S. S. et al. New tricyclic geldanamycin analogues from an engineered strain of Streptomyces hygroscopicus JCM4427. Tetrahedron Lett. 51, 351-353 (2010).
19. Lee, D. et al. Biosynthesis of the heat-shock protein 90 inhibitor geldanamycin: new insight into the formation of the benzoquinone moiety. ChemBioChem. 7, 246-248 (2006).
20. Lee, K. et al. Synthesis and anticancer activity of geldanamycin derivatives derived from biosynthetically generated metabolites. Org. Biomol. Chem. 6, 340-348 (2008).