Mechanism-based inhibitors of MenE, an acyl-CoA synthetase involved in bacterial menaquinone biosynthesis

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 22, 2008, Pages 5963-5966

  Lu, Xuequan ^a   Zhang, Huaning ^b   Tonge, Peter J ^b   Tan, Derek S ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b STONY BROOK UNIVERSITY   (United States)

Author keywords

Acyl CoA synthetase; Antibiotic; Mechanism based inhibitor; Mycobacterium tuberculosis; Staphylococcus aureus

Indexed keywords

2 SUCCINYLBENZOIC ACID; BENZOIC ACID DERIVATIVE; ENZYME INHIBITOR; LONG CHAIN FATTY ACID COENZYME A LIGASE; MENAQUINONE; PROTEIN MENE; SULFAMIC ACID DERIVATIVE; SULFAMIDE DERIVATIVE; UNCLASSIFIED DRUG; VINYL SULFONAMIDE DERIVATIVE;

ADENYLATION; ARTICLE; ENZYME INHIBITION; ESTERIFICATION; IC 50; MYCOBACTERIUM TUBERCULOSIS; RESPIRATORY CHAIN; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; COENZYME A LIGASES; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; STAPHYLOCOCCUS AUREUS; VITAMIN K 2;

BACTERIA (MICROORGANISMS); MENE; MYCOBACTERIUM TUBERCULOSIS; STAPHYLOCOCCUS AUREUS;

EID: 55249100482     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.07.130     Document Type: Article

References (46)

1. Janin Y.L. Bioorg. Med. Chem. 15 (2007) 2479
2. de Lencastre H., Oliveira D., and Tomasz A. Curr. Opin. Microbiol. 10 (2007) 428
3. Bishop D.H.L., Pandya K.P., and King H.K. Biochem. J. 83 (1962) 606
4. Collins M.D., and Jones D. Microbiol. Rev. 45 (1981) 316
5. Lester R.L., and Crane F.L. J. Biol. Chem. 234 (1959) 2169
6. Dowd P., Ham S.-W., Naganathan S., and Hershline R. Annu. Rev. Nutr. 15 (1995) 419
7. Truglio J.J., Theis K., Feng Y., Gajda R., Machutta C., Tonge P.J., and Kisker C. J. Biol. Chem. 278 (2003) 42352
8. Begley T.P., Kinsland C., Taylor S., Tandon M., Nicewonger R., Wu M., Chiu H.-J., Kelleher N., Campobasso N., and Zhang Y. Topics Curr. Chem. 195 (1998) 93
9. Meganathan R. Vitam. Horm. 61 (2001) 173
10. Jiang M., Chen X., Guo Z.-F., Cao Y., Chen M., and Guo Z. Biochemistry 47 (2008) 3426
11. Guest J.R. J. Bacteriol. 130 (1977) 1038
12. Sassetti C.M., Boyd D.H., and Rubin E.J. Mol. Microbiol. 48 (2003) 77
13. Driscoll J.R., and Taber H.W. J. Bacteriol. 174 (1992) 5063
14. Sharma V., Hudspeth M.E.S., and Meganathan R. Gene 168 (1996) 43
15. Gulick A.M., Starai V.J., Horswill A.R., Homick K.M., and Escalante-Semerena J.C. Biochemistry 42 (2003) 2866
16. Gulick A.M., Lu X., and Dunaway-Mariano D. Biochemistry 43 (2004) 8670
17. Jogl G., and Tong L. Biochemistry 43 (2004) 1425
18. Hisanaga Y., Ago H., Nakagawa N., Hamada K., Ida K., Yamamoto M., Hori T., Arii Y., Sugahara M., Kuramitsu S., Yokoyama S., and Miyano M. J. Biol. Chem. 279 (2004) 31717
19. Conti E., Stachelhaus T., Marahiel M.A., and Brick P. EMBO J. 16 (1997) 4174
20. May J.J., Kessler N., Marahiel M.A., and Stubbs M.T. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 12120
21. Nakatsu T., Ichiyama S., Hiratake J., Saldanha A., Kobashi N., Sakata K., and Kato H. Nature 440 (2006) 372
22. Ibba M., and Soll D. Annu. Rev. Biochem. 69 (2000) 617
23. Reviewed in. Cisar J.S., and Tan D.S. Chem. Soc. Rev. 37 (2008) 1320
24. Ueda H., Shoku Y., Hayashi N., Mitsunaga J., In Y., Doi M., Inoue M., and Ishida T. Biochim. Biophys. Acta 1080 (1991) 126
25. Finking R., Neumueller A., Solsbacher J., Konz D., Kretzschmar G., Schweitzer M., Krumm T., and Marahiel M.A. ChemBioChem 4 (2003) 903
26. May J.J., Finking R., Wiegeshoff F., Weber T.T., Bandur N., Koert U., and Marahiel M.A. FEBS J. 272 (2005) 2993
27. Ferreras J.A., Ryu J.-S., Di Lello F., Tan D.S., and Quadri L.E.N. Nat. Chem. Biol. 1 (2005) 29
28. Somu R.V., Boshoff H., Qiao C., Bennett E.M., Barry III C.E., and Aldrich C.C. J. Med. Chem. 49 (2006) 31
29. Miethke M., Bisseret P., Beckering C.L., Vignard D., Eustache J., and Marahiel M.A. FEBS J. 273 (2006) 409
30. Pfleger B.F., Lee J.Y., Somu R.V., Aldrich C.C., Hanna P.C., and Sherman D.H. Biochemistry 46 (2007) 4147
31. Cisar J.S., Ferreras J.A., Soni R.K., Quadri L.E.N., and Tan D.S. J. Am. Chem. Soc. 129 (2007) 7752
32. Ferreras J.A., Stirrett K.L., Lu X., Ryu J.-S., Soll C.E., Tan D.S., and Quadri L.E.N. Chem. Biol. 15 (2008) 51
33. Waller C.W., Patrick J.B., Fulmor W., and Meyer W.E. J. Am. Chem. Soc. 79 (1957) 1011
34. Isono K., Uramoto M., Kusakabe H., Miyata N., Koyama T., Ubukata M., Sethi S.K., and McCloskey J.A. J. Antibiot. 37 (1984) 670
35. Kolkmann R., and Leistner E. Tetrahedron Lett. 26 (1985) 1703
36. Kolkmann R., and Leistner E. Z. Naturforsch., C: Biosci. 42 (1987) 542
37. Santos M.M.M., and Moreira R. Mini-Rev. Med. Chem. 7 (2007) 1040
38. Worthington A.S., Rivera H., Torpey J.W., Alexander M.D., and Burkart M.D. ACS Chem. Biol. 1 (2006) 687
39. Qiao C., Wilson D.J., Bennett E.M., and Aldrich C.C. J. Am. Chem. Soc. 129 (2007) 6350
40. Reddick J.J., Cheng J., and Roush W.R. Org. Lett. 5 (2003) 1967
41. Roser W. Chem. Ber. 17 (1884) 2770
42. Harris Jr. G.D., Herr R.J., and Weinreb S.M. J. Org. Chem. 58 (1993) 5452
43. Carretero J.C., and Ghosez L. Tetrahedron Lett. 28 (1987) 1101
44. Carretero J.C., Demillequand M., and Ghosez L. Tetrahedron 43 (1987) 5125
45. See Supplementary data for full details.
46. 14g.