The Abyssomicin C family as in vitro inhibitors of Mycobacterium tuberculosis

Tuberculosis

Volumn 90, Issue 5, 2010, Pages 298-300

  Freundlich, Joel S ^a   Lalgondar, Mallikarjun ^a   Wei, Jun Rong ^b   Swanson, Stephanie ^a   Sorensen, Erik J ^c   Rubin, Eric J ^b   Sacchettini, James C ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b HARVARD SCHOOL OF PUBLIC HEALTH   (United States)

^c PRINCETON UNIVERSITY   (United States)

Author keywords

Abyssomicin; Mycobacterium tuberculosis; p Aminobenzoate metabolism

Indexed keywords

ABYSSOMICIN C; ISONIAZID; NATURAL PRODUCT; RIFAMPICIN; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERICIDAL ACTIVITY; CONTROLLED STUDY; DRUG EFFICACY; DRUG SYNTHESIS; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM BOVIS; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

4-AMINOBENZOIC ACID; ANTITUBERCULAR AGENTS; BACILLUS SUBTILIS; BICYCLO COMPOUNDS, HETEROCYCLIC; HUMANS; ISOMERISM; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM BOVIS; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS;

EID: 77957197443     PISSN: 14729792     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tube.2010.08.002     Document Type: Article

References (23)

1. World Health Organization Global tuberculosis control report. 2009.
2. J.C. Sacchettini, E.J. Rubin, and J.S. Freundlich Drugs versus bugs: in pursuit of the persistent predator Mycobacterium tuberculosis Nat Rev Microbiol 6 2008 41 52
3. M. Jassal, and W.R. Bishai Extensively drug-resistant tuberculosis Lancet Infect Dis 9 2009 19 30
4. K. Andries, P. Verhasselt, J. Guillemont, H.W.H. Gohlmann, J.-M. Neefs, and H. Winkler A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis Science 307 2005 223 227
5. C.K. Stover, P. Warrener, D.R. VanDevanter, D.R. Sherman, T.M. Arain, and M.H. Langhorne A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis Nature 405 2000 962 966
6. B. Bister, D. Bischoff, M. Ströbele, J. Riedlinger, A. Reicke, and F. Wolter Abyssomicin C-A polycyclic antibiotic from a marine Verrucosispora strain as an inhibitor of the p-aminobenzoic acid/tetrahydrofolate biosynthesis pathway Angew Chem Int Ed Engl 43 2004 2574 2576
7. J. Riedlinger, A. Reicke, H. Zähner, B. Krismer, A.T. Bull, and L.A. Maldonado Abyssomicins, inhibitors of the para-aminobenzoic acid pathway produced by the marine Verrucosispora strain AB-18-032 J Antibiot 57 2004 271 279
8. C.W. Zapf, B.A. Harrison, C. Drahl, and E.J. Sorensen A Diels-Alder macrocyclization enables an efficient asymmetric synthesis of the antibacterial natural product abyssomicin C Angew Chem Int Ed Engl 44 2005 6533 6537
9. K.C. Nicolaou, and S.T. Harrison Total synthesis of abyssomicin C and atrop-abyssomicin C Angew Chem Int Ed Engl 45 2006 3256 3260
10. S. Keller, G. Nicholson, C. Drahl, E. Sorensen, H.-P. Fielder, and R.D. Süssmuth Abyssomicins G and H and atrop-abyssomicin C from the marine Verrucosispora strain AB-18-032 J Antibiot (Tokyo) 60 2007 391 394
11. S.T. Cole, R. Brosch, J. Parkhill, T. Garnier, C. Churcher, and D. Harris Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence Nature 393 1998 537 544
12. G. Lamichhane, M. Zignol, N.J. Blades, D.E. Geiman, A. Dougherty, and J. Grosset A postgenomic method for predicting essential genes at subsaturation levels of mutagenesis: application to Mycobacterium tuberculosis Proc Natl Acad Sci USA 100 2003 7213 7218
13. C.M. Sassetti, D.H. Boyd, and E.J. Rubin Comprehensive identification of conditionally essential genes in mycobacteria Proc Natl Acad Sci USA 2001 2001 12712 12717
14. C.M. Sassetti, D.H. Boyd, and E.J. Rubin Genes required for mycobacterial growth defined by high density mutagenesis Mol Microbiol 48 2003 77 84
15. B.B. Snider, and Y. Zou Synthesis of the carbocyclic skeleton of abyssomicins C and D Org Lett 7 2005 4939 4941
16. E.A. Couladouros, E.A. Bouzas, and A.D. Magos Formal synthesis of abyssomicin C Tetrahedron 62 2006 5272 5279
17. S.B. Snapper, R.E. Melton, S. Mustafa, T. Kieser, and W.R. Jacobs Jr. Isolation and characterization of efficient plasmid transformation mutants of Mycobacterium smegmatis Mol Microbiol 4 1990 1911 1919
18. S.G. Franzblau, R.S. Witzig, J.C. McLaughlin, P. Torres, G. Madico, and A. Hernandez Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay J Clin Microbiol 36 1998 362 366
19. K.C. Nicolaou, and S.T. Harrison Total synthesis of abyssomicin C, atrop-abyssomicin C, and abyssomicin D: implications for natural origins of atrop-abyssomicin C J Am Chem Soc 129 2007 429 440
20. C. Vilchze, F. Wang, M. Arai, M.H. Hazbon, R. Colangeli, and L. Kremer Transfer of a point mutation in Mycobacterium tuberculosis inhA resolves the target of isoniazid Nat Med 12 2006 1027 1029
21. J. Rengarajan, C.M. Sassetti, V. Naroditskaya, A. Sloutsky, B.R. Bloom, and E.J. Rubin The folate pathway is a target for resistance to the drug para-aminosalicylic acid (PAS) in mycobacteria Mol Microbiol 53 2004 275 282
22. G.P. Youmans, G.W. Raleigh, and A.S. Youmans The tuberculostatic action of para-aminosalicyclic acid J Bacteriol 54 1947 409 416
23. C.F. Drahl Chemical synthesis and activity-based proteomic studies of the abyssomicins, protein-reactive natural products 2007 Princeton University