Discovery of kibdelomycin, a potent new class of bacterial type II topoisomerase inhibitor by chemical-genetic profiling in Staphylococcus aureus

Chemistry and Biology

Volumn 18, Issue 8, 2011, Pages 955-965

  Phillips, John W ^a,c   Goetz, Michael A ^a   Smith, Scott K ^a   Zink, Deborah L ^a   Polishook, Jon ^a   Onishi, Russell ^a   Salowe, Scott ^a   Wiltsie, Judyann ^a   Allocco, John ^a   Sigmund, Janet ^a   Dorso, Karen ^a   Lee, Suzy ^a   Skwish, Stephen ^a   De La Cruz, Mercedes ^b,d   Martín, Jesús ^b,d   Vicente, Francisca ^b,d   Genilloud, Olga ^b,d   Lu, Jun ^a   Painter, Ronald E ^a   Young, Katherine ^a   Overbye, Karen ^a   Donald, Robert G K ^a   Singh, Sheo B ^a   more..

^a MERCK RESEARCH LABORATORIES   (United States)

^b Medical affairs Merck sharp and Dohme ltd   (Spain)

^c ALLEN INSTITUTE FOR BRAIN SCIENCE   (United States)

^d Fundacion MEDINA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE IV; GYRASE INHIBITOR;

ACTINOMYCETALES; ANTIBIOTIC RESISTANCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; GENETICS; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGICAL EXAMINATION; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS INFECTION;

ACTINOMYCETALES; ANTI-BACTERIAL AGENTS; DNA GYRASE; DNA TOPOISOMERASE IV; DRUG RESISTANCE, BACTERIAL; HUMANS; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; STAPHYLOCOCCAL INFECTIONS; STAPHYLOCOCCUS AUREUS; TOPOISOMERASE II INHIBITORS;

BACTERIA (MICROORGANISMS); KIBDELOSPORANGIUM; POSIBACTERIA; STAPHYLOCOCCUS AUREUS;

EID: 80052153483     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2011.06.011     Document Type: Article

References (39)

1. G.F. Bills, G. Platas, A. Fillola, M.R. Jiménez, J. Collado, F. Vicente, J. Martín, A. González, J. Bur-Zimmermann, J.R. Tormo, and F. Peláez Enhancement of antibiotic and secondary metabolite detection from filamentous fungi by growth on nutritional arrays J. Appl. Microbiol. 104 2008 1644 1658 (Pubitemid 351724994)
2. C.R. Chen, M. Malik, M. Snyder, and K. Drlica DNA gyrase and topoisomerase IV on the bacterial chromosome: quinolone-induced DNA cleavage J. Mol. Biol. 258 1996 627 637 (Pubitemid 26145906)
3. R.G. Donald, S. Skwish, R.A. Forsyth, J.W. Anderson, T. Zhong, C. Burns, S. Lee, X. Meng, L. LoCastro, and L.W. Jarantow A Staphylococcus aureus fitness test platform for mechanism-based profiling of antibacterial compounds Chem. Biol. 16 2009 826 836
4. O. Genilloud, I. González, O. Salazar, J. Martín, J.R. Tormo, and F. Vicente Current approaches to exploit actinomycetes as a source of novel natural products J. Ind. Microbiol. Biotechnol. 38 2011 375 389
5. M.A. Goetz, C. Zhang, D.L. Zink, M. Arocho, F. Vicente, G.F. Bills, J. Polishook, K. Dorso, R. Onishi, and C. Gill Coelomycin, a highly substituted 2,6-dioxo-pyrazine fungal metabolite antibacterial agent discovered by Staphylococcus aureus fitness test profiling J. Antibiot. 63 2010 512 518
6. M. Hayakawa, H. Iino, S. Takeuchi, and T. Yamazaki Application of a method incorporating treatment with chloramine-T for the selective isolation of Streptosporangiaceae from soil J. Ferment. Bioeng. 84 1997 599 602 (Pubitemid 128752702)
7. K. Herath, G. Harris, H. Jayasuriya, D. Zink, S. Smith, F. Vicente, G. Bills, J. Collado, A. González, and B. Jiang Isolation, structure and biological activity of phomafungin, a cyclic lipodepsipeptide from a widespread tropical Phoma sp Bioorg. Med. Chem. 17 2009 1361 1369
8. J. Huber, R.G. Donald, S.H. Lee, L.W. Jarantow, M.J. Salvatore, X. Meng, R. Painter, R.H. Onishi, J. Occi, and K. Dorso Chemical genetic identification of peptidoglycan inhibitors potentiating carbapenem activity against methicillin-resistant Staphylococcus aureus Chem. Biol. 16 2009 837 848
9. H. Jayasuriya, K.B. Herath, C. Zhang, D.L. Zink, A. Basilio, O. Genilloud, M.T. Diez, F. Vicente, I. Gonzalez, and O. Salazar Isolation and Structure of Platencin: A Novel FabH and FabF Dual Inhibitor with Potent Broad Spectrum Antibiotic Activity Produced by Streptomyces platensis MA7339 Angew. Chem. Int. Ed. 46 2007 4684 4688 (Pubitemid 46997463)
10. B. Jiang, D. Xu, J. Allocco, C. Parish, J. Davison, K. Veillette, S. Sillaots, W. Hu, R. Rodriguez-Suarez, and S. Trosok PAP inhibitor with in vivo efficacy identified by Candida albicans genetic profiling of natural products Chem. Biol. 15 2008 363 374 (Pubitemid 351508424)
11. T.H. Jukes, and C. Cantor Evolution.of Protein Molecules H.N. Munro, J.B. Allison, Mammalian Protein Metabolism 1969 Academic Press New York 21 132
12. R.M. Klevens, M.A. Morrison, J. Nadle, S. Petit, K. Gershman, S. Ray, L.H. Harrison, R. Lynfield, G. Dumyati, J.M. Townes Active Bacterial Core surveillance (ABCs) MRSA Investigators Invasive methicillin-resistant Staphylococcus aureus infections in the United States JAMA 298 2007 1763 1771 (Pubitemid 47598444)
13. S. Kodali, A. Galgoci, K. Young, R. Painter, L.L. Silver, K.B. Herath, S.B. Singh, D. Cully, J.F. Barrett, D. Schmatz, and J. Wang Determination of selectivity and efficacy of fatty acid synthesis inhibitors J. Biol. Chem. 280 2005 1669 1677
14. V. Lamour, L. Hoermann, J.-M. Jeltsch, P. Oudet, and D. Moras An open conformation of the Thermus thermophilus gyrase B ATP-binding domain J. Biol. Chem. 277 2002 18947 18953 (Pubitemid 34952456)
15. S.E. Luria, and M. Delbrück Mutations of bacteria from virus sensitivity to virus resistance Genetics 28 1943 491 511
16. A. Maxwell, and D.M. Lawson The ATP-binding site of type II topoisomerases as a target for antibacterial drugs Curr. Top. Med. Chem. 3 2003 283 303
17. M. Oblak, M. Kotnik, and T. Solmajer Discovery and development of ATPase inhibitors of DNA gyrase as antibacterial agents Curr. Med. Chem. 14 2007 2033 2047 (Pubitemid 47578161)
18. J.G. Ondeyka, D.L. Zink, K. Young, R. Painter, S. Kodali, A. Galgoci, J. Collado, J.R. Tormo, A. Basilio, and F. Vicente Discovery of bacterial fatty acid synthase inhibitors from a Phoma species as antimicrobial agents using a new antisense-based strategy J. Nat. Prod. 69 2006 377 380
19. J.G. Ondeyka, D. Zink, A. Basilio, F. Vicente, G. Bills, M.T. Diez, M. Motyl, G. Dezeny, K. Byrne, and S.B. Singh Coniothyrione, a chlorocyclopentandienylbenzopyrone as a bacterial protein synthesis inhibitor discovered by antisense technology J. Nat. Prod. 70 2007 668 670 (Pubitemid 46797878)
20. J. Ondeyka, G. Harris, D. Zink, A. Basilio, F. Vicente, G. Bills, G. Platas, J. Collado, A. Gonzáez, and M. de la Cruz Isolation, structure elucidation, and biological activity of virgineone from Lachnum Wirgineum using the genome-wide Candida albicans fitness test J. Nat. Prod. 72 2009 136 141
21. C.A. Parish, S.K. Smith, K. Calati, D. Zink, K. Wilson, T. Roemer, B. Jiang, D. Xu, G. Bills, and G. Platas Isolation and structure elucidation of parnafungins, antifungal natural products that inhibit mRNA polyadenylation J. Am. Chem. Soc. 130 2008 7060 7066 (Pubitemid 351770148)
22. M.N. Rivetna, S.P. Salowe, R.L. Tolman, and A.B. Jones A Medicinal Chemistry Evaluation of the Autoinhibitory Domain of Calcineurin Bioorg. Med. Chem. Lett. 5 1995 1147 1150
23. N. Saitou, and M. Nei The neighbor-joining method: a new method for reconstructing phylogenetic trees Mol. Biol. Evol. 4 1987 406 425
24. S.B. Singh, and J.F. Barrett Empirical antibacterial drug discovery - foundation in natural products Biochem. Pharmacol. 71 2006 1006 1015
25. S.B. Singh, H. Jayasuriya, J.G. Ondeyka, K.B. Herath, C. Zhang, D.L. Zink, N.N. Tsou, R.G. Ball, A. Basilio, and O. Genilloud Isolation, structure, and absolute stereochemistry of platensimycin, a broad spectrum antibiotic discovered using an antisense differential sensitivity strategy J. Am. Chem. Soc. 128 2006 11916-11920 and 15547 (Pubitemid 44360228)
26. S.B. Singh, D.L. Zink, J. Huber, O. Genilloud, O. Salazar, M.T. Diez, A. Basilio, F. Vicente, and K.M. Byrne Discovery of lucensimycins A and B from Streptomyces lucensis MA7349 using an antisense strategy Org. Lett. 8 2006 5449 5452
27. S.B. Singh, J.W. Phillips, and J. Wang Highly sensitive target-based whole-cell antibacterial discovery strategy by antisense RNA silencing Curr. Opin. Drug Discov. Devel. 10 2007 160 166 (Pubitemid 46438645)
28. S.B. Singh, D.L. Zink, K.B. Herath, O. Salazar, and O. Genilloud Discovery and antibacterial activity of lucensimycin C from Streptomyces lucensis Tetrahedron Lett. 49 2008 2616 2619
29. S.B. Singh, D.L. Zink, K. Dorso, M. Motyl, O. Salazar, A. Basilio, F. Vicente, K.M. Byrne, S. Ha, and O. Genilloud Isolation, structure, and antibacterial activities of lucensimycins D-G, discovered from Streptomyces lucensis MA7349 using an antisense strategy J. Nat. Prod. 72 2009 345 352
30. S. Tohyama, Y. Takahashi, and Y. Akamatsu Biosynthesis of amycolamicin: the biosynthetic origin of a branched alpha-aminoethyl moiety in the unusual sugar amycolose J. Antibiot. 63 2010 147 149
31. F.T. Tsai, O.M. Singh, T. Skarzynski, A.J. Wonacott, S. Weston, A. Tucker, R.A. Pauptit, A.L. Breeze, J.P. Poyser, and R. O'Brien The high-resolution crystal structure of a 24-kDa gyrase B fragment from E. coli complexed with one of the most potent coumarin inhibitors, clorobiocin Proteins 28 1997 41 52 (Pubitemid 27194017)
32. J. Wang, A. Galgoci, S. Kodali, K.B. Herath, H. Jayasuriya, K. Dorso, F. Vicente, A. González, D. Cully, D. Bramhill, and S. Singh Discovery of a small molecule that inhibits cell division by blocking FtsZ, a novel therapeutic target of antibiotics J. Biol. Chem. 278 2003 44424 44428 (Pubitemid 37377193)
33. J. Wang, S.M. Soisson, K. Young, W. Shoop, S. Kodali, A. Galgoci, R. Painter, G. Parthasarathy, Y.S. Tang, and R. Cummings Platensimycin is a selective FabF inhibitor with potent antibiotic properties Nature 441 2006 358 361 (Pubitemid 44050201)
34. J. Wang, S. Kodali, S.H. Lee, A. Galgoci, R. Painter, K. Dorso, F. Racine, M. Motyl, L. Hernandez, and E. Tinney Discovery of platencin, a dual FabF and FabH inhibitor with in vivo antibiotic properties Proc. Natl. Acad. Sci. USA 104 2007 7612 7616 (Pubitemid 47185954)
35. D. Xu, B. Jiang, T. Ketela, S. Lemieux, K. Veillette, N. Martel, J. Davison, S. Sillaots, S. Trosok, and C. Bachewich Genome-wide fitness test and mechanism-of-action studies of inhibitory compounds in Candida albicans PLoS Pathog. 3 2007 e92
36. K. Young Vitro antibacterial resistance selection and quantitation S.J. Enna, M. Williams, J.F. Barret, J.W. Ferkany, T. Kenakin, R.D. Porsolt, Current Protocols in Pharmacology Unit 13A.6 2006 John Wiley & Sons, Inc. Hoboken, NJ
37. K. Young, H. Jayasuriya, J.G. Ondeyka, K. Herath, C. Zhang, S. Kodali, A. Galgoci, R. Painter, V. Brown-Driver, and R. Yamamoto Discovery of FabH/FabF inhibitors from natural products Antimicrob. Agents Chemother. 50 2006 519 526 (Pubitemid 43190961)
38. C. Zhang, J.G. Ondeyka, D.L. Zink, A. Basilio, F. Vicente, J. Collado, G. Platas, J. Huber, K. Dorso, and M. Motyl Isolation, structure and antibacterial activity of pleosporone from a pleosporalean ascomycete discovered by using antisense strategy Bioorg. Med. Chem. 17 2009 2162 2166
39. C. Zhang, J.G. Ondeyka, D.L. Zink, A. Basilio, F. Vicente, O. Salazar, O. Genilloud, K. Dorso, M. Motyl, K. Byrne, and S.B. Singh Discovery of okilactomycin and congeners from Streptomyces scabrisporus by antisense differential sensitivity assay targeting ribosomal protein S4 J. Antibiot. 62 2009 55 61