Construction of a microbial natural product library for chemical biology studies

Current Opinion in Chemical Biology

Volumn 16, Issue 1-2, 2012, Pages 101-108

  Kato, Naoki ^a   Takahashi, Shunji ^a   Nogawa, Toshihiko ^a   Saito, Tamio ^a   Osada, Hiroyuki ^a  

^a RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FUMITREMORGIN C; MICROBIAL PRODUCTS NOT CLASSIFIED ELSEWHERE; OXYGENASE; POLYKETIDE SYNTHASE;

ACTINOBACTERIA; BIOSYNTHESIS; DATA BASE; DRUG SYNTHESIS; FUNGUS; GENETIC ENGINEERING; HUMAN; IN VITRO STUDY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; MOLECULAR LIBRARY; MOLECULAR PROBE; NONHUMAN; REVIEW;

ANIMALS; BACTERIA; BIOLOGICAL AGENTS; DATABASES, FACTUAL; HUMANS; INTERNET; PROTEIN ENGINEERING;

EID: 84859629072     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2012.02.016     Document Type: Review

References (50)

1. Osada H. Bioprobes: Biochemical Tools for Investigating Cell Function 2000, Springer.
2. Yoshida M., Kijima M., Akita M., Beppu T. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A. J Biol Chem 1990, 265:17174-17179.
3. Harding M.W., Galat A., Uehling D.E., Schreiber S.L. A receptor for the immunosuppressant FK506 is a cis-trans peptidyl-prolyl isomerase. Nature 1989, 341:758-760.
4. Koehn F.E., Carter G.T. The evolving role of natural products in drug discovery. Nat Rev Drug Discov 2005, 4:206-220.
5. Li Q., Cheng T., Wang Y., Bryant S.H. PubChem as a public resource for drug discovery. Drug Discov Today 2010, 15:1052-1057.
6. Osada H. Introduction of new tools for chemical biology research on microbial metabolites. Biosci Biotechnol Biochem 2010, 74:1135-1140.
7. Watanabe N., Sekine T., Takagi M., Iwasaki J., Imamoto N., Kawasaki H., Osada H. Deficiency in chromosome congression by the inhibition of Plk1 polo box domain-dependent recognition. J Biol Chem 2009, 284:2344-2353.
8. Miyazaki I., Simizu S., Okumura H., Takagi S., Osada H. A small-molecule inhibitor shows that pirin regulates migration of melanoma cells. Nat Chem Biol 2010, 6:667-673.
9. Wierzba K., Muroi M., Osada H. Proteomics accelerating the identification of the target molecule of bioactive small molecules. Curr Opin Chem Biol 2011, 15:57-65.
10. Newman D.J., Cragg G.M. Natural products as sources of new drugs over the last 25 years. J Nat Prod 2007, 70:461-477.
11. Wetzel S., Bon R.S., Kumar K., Waldmann H. Biology-oriented synthesis. Angew Chem Int Ed Engl 2011, 50:10800-10826.
12. Grabowski K., Baringhaus K.H., Schneider G. Scaffold diversity of natural products: inspiration for combinatorial library design. Nat Prod Rep 2008, 25:892-904.
13. Winter J.M., Behnken S., Hertweck C. Genomics-inspired discovery of natural products. Curr Opin Chem Biol 2011, 15:22-31.
14. Bumpus S.B., Evans B.S., Thomas P.M., Ntai I., Kelleher N.L. A proteomics approach to discovering natural products and their biosynthetic pathways. Nat Biotechnol 2009, 27:951-956.
15. Kersten R.D., Yang Y.L., Xu Y., Cimermancic P., Nam S.J., Fenical W., Fischbach M.A., Moore B.S., Dorrestein P.C. A mass spectrometry-guided genome mining approach for natural product peptidogenomics. Nat Chem Biol 2011, 7:794-802.
16. Evans B.E., Rittle K.E., Bock M.G., DiPardo R.M., Freidinger R.M., Whitter W.L., Lundell G.F., Veber D.F., Anderson P.S., Chang R.S., et al. Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists. J Med Chem 1988, 31:2235-2246.
17. Harvey A.L. Natural products in drug discovery. Drug Discov Today 2008, 13:894-901.
18. Kingston D.G. Modern natural products drug discovery and its relevance to biodiversity conservation. J Nat Prod 2011, 74:496-511.
19. Osada H., Nogawa T. Systematic isolation of microbial metabolites for natural products depository (NPDepo). Pure Appl Chem 2012, 10.1351/PAC-CON-11-08-11.
20. Bugni T.S., Richards B., Bhoite L., Cimbora D., Harper M.K., Ireland C.M. Marine natural product libraries for high-throughput screening and rapid drug discovery. J Nat Prod 2008, 71:1095-1098.
21. Johnson T.A., Sohn J., Inman W.D., Estee S.A., Loveridge S.T., Vervoort H.C., Tenney K., Liu J., Ang K.K., Ratnam J., et al. Natural product libraries to accelerate the high-throughput discovery of therapeutic leads. J Nat Prod 2011, 74:2545-2555.
22. Camp D., Davis R.A., Campitelli M., Ebdon J., Quinn R.J. Drug-like properties: guiding principles for the design of natural product libraries. J Nat Prod 2012, 75:72-81.
23. Nogawa T., Takahashi S., Okano A., Kawatani M., Uramoto M., Saito T., Osada H. Spirotoamides A and B, novel 6,6-spiroacetal polyketides isolated from a microbial metabolite fraction library. J Antibiot 2012, 10.1038/ja.2011.121.
24. Nogawa T., Okano A., Takahashi S., Uramoto M., Konno H., Saito T., Osada H. Verticilactam, a new macrolactam isolated from a microbial metabolite fraction library. Org Lett 2010, 12:4564-4567.
25. Cheng X.C., Kihara T., Ying X., Uramoto M., Osada H., Kusakabe H., Wang B.N., Kobayashi Y., Ko K., Yamaguchi I., et al. A new antibiotic, tautomycetin. J Antibiot 1989, 42:141-144.
26. Mitsuhashi S., Matsuura N., Ubukata M., Oikawa H., Shima H., Kikuchi K. Tautomycetin is a novel and specific inhibitor of serine/threonine protein phosphatase type 1, PP1. Biochem Biophys Res Commun 2001, 287:328-331.
27. MacKintosh C., Klumpp S. Tautomycin from the bacterium Streptomyces verticillatus. Another potent and specific inhibitor of protein phosphatases 1 and 2A. FEBS Lett 1990, 277:137-140.
28. Cheng X.C., Kihara T., Kusakabe H., Magae J., Kobayashi Y., Fang R.P., Ni Z.F., Shen Y.C., Ko K., Yamaguchi I., et al. A new antibiotic, tautomycin. J Antibiot 1987, 40:907-909.
29. Panthee S., Takahashi S., Takagi H., Nogawa T., Oowada E., Uramoto M., Osada H. Furaquinocins I and J: novel polyketide isoprenoid hybrid compounds from Streptomyces reveromyceticus SN-593. J Antibiot 2011, 64:509-513.
30. Takahashi S., Takagi H., Toyoda A., Uramoto M., Nogawa T., Ueki M., Sakaki Y., Osada H. Biochemical characterization of a novel indole prenyltransferase from Streptomyces sp. SN-593. J Bacteriol 2010, 192:2839-2851.
31. Osada H., Koshino H., Isono K., Takahashi H., Kawanishi G. Reveromycin A, a new antibiotic which inhibits the mitogenic activity of epidermal growth factor. J Antibiot 1991, 44:259-261.
32. Woo J.T., Kawatani M., Kato M., Shinki T., Yonezawa T., Kanoh N., Nakagawa H., Takami M., Lee K.H., Stern P.H., et al. Reveromycin A, an agent for osteoporosis, inhibits bone resorption by inducing apoptosis specifically in osteoclasts. Proc Natl Acad Sci USA 2006, 103:4729-4734.
33. Rabindran S.K., He H., Singh M., Brown E., Collins K.I., Annable T., Greenberger L.M. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgin C. Cancer Res 1998, 58:5850-5858.
34. Rabindran S.K., Ross D.D., Doyle L.A., Yang W., Greenberger L.M. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res 2000, 60:47-50.
35. Takahashi S., Toyoda A., Sekiyama Y., Takagi H., Nogawa T., Uramoto M., Suzuki R., Koshino H., Kumano T., Panthee S., et al. Reveromycin A biosynthesis uses RevG and RevJ for stereospecific spiroacetal formation. Nat Chem Biol 2011, 7:461-468.
36. Maiya S., Grundmann A., Li S.M., Turner G. The fumitremorgin gene cluster of Aspergillus fumigatus: identification of a gene encoding brevianamide F synthetase. Chembiochem 2006, 7:1062-1069.
37. Burg R.W., Miller B.M., Baker E.E., Birnbaum J., Currie S.A., Hartman R., Kong Y.L., Monaghan R.L., Olson G., Putter I., et al. Avermectins, new family of potent anthelmintic agents: producing organism and fermentation. Antimicrob Agents Chemother 1979, 15:361-367.
38. Ishihara H., Martin B.L., Brautigan D.L., Karaki H., Ozaki H., Kato Y., Fusetani N., Watabe S., Hashimoto K., Uemura D., et al. Calyculin A and okadaic acid: inhibitors of protein phosphatase activity. Biochem Biophys Res Commun 1989, 159:871-877.
39. Bialojan C., Takai A. Inhibitory effect of a marine-sponge toxin, okadaic acid, on protein phosphatases. Specificity and kinetics. Biochem J 1988, 256:283-290.
40. Agtarap A., Chamberlin J.W., Pinkerton M., Steinrauf L. The structure of monensic acid, a new biologically active compound. J Am Chem Soc 1967, 89:5737-5739.
41. Niggemann J., Bedorf N., Flörke U., Steinmetz H., Gerth K., Reichenbach H., Höfle G. Spirangien A and B, highly cytotoxic and antifungal spiroketals from the myxobacterium Sorangium cellulosum: isolation. structure elucidation and chemical modifications. Eur J Org Chem 2005, 2005:5013-5018.
42. Shimizu T., Masuda T., Hiramoto K., Nakata T. Total synthesis of reveromycin A. Org Lett 2000, 2:2153-2156.
43. Sheppeck J.E., Liu W., Chamberlin A.R. Total synthesis of the serine/threonine-specific protein phosphatase inhibitor tautomycin (1). J Org Chem 1997, 62:387-398.
44. Paterson I., Findlay A.D., Noti C. Total synthesis of (-)-spirangien A, an antimitotic polyketide isolated from the myxobacterium Sorangium cellulosum. Chem Asian J 2009, 4:594-611.
45. Shimizu T., Usui T., Fujikura M., Kawatani M., Satoh T., Machida K., Kanoh N., Woo J.T., Osada H., Sodeoka M. Synthesis and biological activities of reveromycin A and spirofungin A derivatives. Bioorg Med Chem Lett 2008, 18:3756-3760.
46. Shimizu T., Usui T., Machida K., Furuya K., Osada H., Nakata T. Chemical modification of reveromycin A and its biological activities. Bioorg Med Chem Lett 2002, 12:3363-3366.
47. Kato N., Suzuki H., Takagi H., Asami Y., Kakeya H., Uramoto M., Usui T., Takahashi S., Sugimoto Y., Osada H. Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus. Chembiochem 2009, 10:920-928.
48. Kato N., Suzuki H., Takagi H., Uramoto M., Takahashi S., Osada H. Gene disruption and biochemical characterization of verruculogen synthase of Aspergillus fumigatus. Chembiochem 2011, 12:711-714.
49. Steffan N., Grundmann A., Afiyatullov S., Ruan H., Li S.M. FtmOx1, a non-heme Fe(II) and α-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus. Org Biomol Chem 2009, 7:4082-4087.
50. Li S.M. Genome mining and biosynthesis of fumitremorgin-type alkaloids in ascomycetes. J Antibiot 2011, 64:45-49.