CoA adducts of 4-oxo-4-phenylbut-2-enoates: Inhibitors of MenB from the M. tuberculosis menaquinone biosynthesis pathway

ACS Medicinal Chemistry Letters

Volumn 2, Issue 11, 2011, Pages 818-823

  Li, Xiaokai ^a   Liu, Nina ^a   Zhang, Huaning ^a   Knudson, Susan E ^b   Li, Huei Jiun ^a   Lai, Cheng Tsung ^a   Simmerling, Carlos ^a   Slayden, Richard A ^b   Tonge, Peter J ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

1,4 dihydroxy 2 naphthoyl CoA synthase; CoA; HTS; Menaquinone; MenB; o succinylbenzoic acid

Indexed keywords

1,4 DIHYDROXY 2 NAPHTHOYL COENZYME A SYNTHASE; 1,4 DIHYDROXY 2 NAPHTHOYL COENZYME A SYNTHASE INHIBITOR; 4 OXO 4 CHLOROPHENYLBUTENOYL METHYL ESTER; 4 OXO 4 PHENYLBUT 2 ENOATE; ACYL COENZYME A; CARBOXYLIC ACID; COENZYME A; ENOYL COENZYME A HYDRATASE; MENAQUINONE; SYNTHETASE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; CELL PERMEABILIZATION; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; HYDROLYSIS; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; PROTEIN FAMILY; PROTEIN MOTIF; STRUCTURE ACTIVITY RELATION;

MYCOBACTERIUM TUBERCULOSIS;

EID: 80955150848     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200141e     Document Type: Article

References (23)

1. Bloom, B. R.; Murray, C. J. Tuberculosis: Commentary on a reemergent killer Science 1992, 257, 1055-1064
2. Boshoff, H. I.; Barry, C. E., 3rd. Tuberculosis-Metabolism and respiration in the absence of growth Nat. Rev. Microbiol. 2005, 3, 70-80
3. Gengenbacher, M.; Rao, S. P.; Pethe, K.; Dick, T. Nutrient-starved, non-replicating Mycobacterium tuberculosis requires respiration, ATP synthase and isocitrate lyase for maintenance of ATP homeostasis and viability Microbiology 2010, 156, 81-87
4. Andries, K.; Verhasselt, P.; Guillemont, J.; Gohlmann, H. W.; Neefs, J. M.; Winkler, H.; Van Gestel, J.; Timmerman, P.; Zhu, M.; Lee, E.; Williams, P.; de Chaffoy, D.; Huitric, E.; Hoffner, S.; Cambau, E.; Truffot-Pernot, C.; Lounis, N.; Jarlier, V. A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis Science 2005, 307, 223-237
5. Lu, X.; Zhang, H.; Tonge, P. J.; Tan, D. S. Mechanism-based inhibitors of MenE, an acyl-CoA synthetase involved in bacterial menaquinone biosynthesis Bioorg. Med. Chem. Lett. 2008, 18, 5963-5966
6. Dhiman, R. K.; Mahapatra, S.; Slayden, R. A.; Boyne, M. E.; Lenaerts, A.; Hinshaw, J. C.; Angala, S. K.; Chatterjee, D.; Biswas, K.; Narayanasamy, P.; Kurosu, M.; Crick, D. C. Menaquinone synthesis is critical for maintaining mycobacterial viability during exponential growth and recovery from non-replicating persistence Mol. Microbiol. 2009, 72, 85-97
7. Meganathan, R. Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): A perspective on enzymatic mechanisms Vitam. Horm. 2001, 61, 173-218 (Pubitemid 33805695)
8. Truglio, J. J.; Theis, K.; Feng, Y.; Gajda, R.; Machutta, C.; Tonge, P. J.; Kisker, C. Crystal Structure of Mycobacterium tuberculosis MenB, a Key Enzyme in Vitamin K2 Biosynthesis J. Biol. Chem. 2003, 278, 42352-42360 (Pubitemid 37310505)
9. Sassetti, C. M.; Boyd, D. H.; Rubin, E. J. Genes required for mycobacterial growth defined by high density mutagenesis Mol. Microbiol. 2003, 48, 77-84 (Pubitemid 36411469)
10. Li, X.; Liu, N.; Zhang, H.; Knudson, S. E.; Slayden, R. A.; Tonge, P. J. Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis Bioorg. Med. Chem. Lett. 2010, 20, 6306-6309
11. Obrien, W. E. Continuous spectrophotometric assay for argininosuccinate synthetase based on pyrophosphate formation Anal. Biochem. 1976, 76, 423-430
12. Jenner, G. Comparative study of physical and chemical activation modes. The case of the synthesis of beta-amino derivatives Tetrahedron 1996, 52, 13557-13568 (Pubitemid 26341947)
13. Powell, P. J.; Thorpe, C. 2-Octynoyl coenzyme A is a mechanism-based inhibitor of pig kidney medium-chain acyl coenzyme A dehydrogenase: isolation of the target peptide Biochemistry 1988, 27, 8022-8028
14. Li, H. J.; Li, X.; Liu, N.; Zhang, H.; Truglio, J. J.; Mishra, S.; Kisker, C. F.; Garcia-Diaz, M.; Tonge, P. J. Mechanism of the Intramolecular Claisen Condensation Reaction Catalyzed by MenB, a Crotonase Superfamily Member. Biochemistry 2011, DOI: 10.1021/bi200877x.
15. Zhang, H.; Machutta, C. A.; Tonge, P. J. Fatty Acid Biosynthesis and Oxidation. In Comprehensive Natural Products Chemistry II Chemistry and Biology; Mander, L.; Lui, H.-W., Eds.; Elsevier: Amsterdam, 2010; Vol. 8, pp 231-275.
16. Hurdle, J. G.; Lee, R. B.; Budha, N. R.; Carson, E. I.; Qi, J.; Scherman, M. S.; Cho, S. H.; McNeil, M. R.; Lenaerts, A. J.; Franzblau, S. G.; Meibohm, B.; Lee, R. E. A microbiological assessment of novel nitrofuranylamides as anti-tuberculosis agents J. Antimicrob. Chemother. 2008, 62, 1037-1045
17. Ramchandra, P.; Sturm, A. W. Expression of the naphthoate synthase gene in Mycobacterium tuberculosis in a self-generated oxygen depleted liquid culture system Anaerobe 2010, 16, 610-613
18. Taber, H. W.; Dellers, E. A.; Lombardo, L. R. Menaquinone biosynthesis in Bacillus subtilis -Isolation of men mutants and evidence for clustering of men genes J. Bacteriol. 1981, 145, 321-327 (Pubitemid 11131873)
19. Pereira, M. P.; Blanchard, J. E.; Murphy, C.; Roderick, S. L.; Brown, E. D. High-throughput screening identifies novel inhibitors of the acetyltransferase activity of Escherichia coli GlmU Antimicrob. Agents Chemother. 2009, 53, 2306-2311
20. Lewis, W. G.; Green, L. G.; Grynszpan, F.; Radic, Z.; Carlier, P. R.; Taylor, P.; Finn, M. G.; Sharpless, K. B. Click chemistry in situ: Acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks Angew. Chem., Int. Ed. Engl. 2002, 41, 1053-1057 (Pubitemid 34251912)
21. Singh, J.; Petter, R. C.; Baillie, T. A.; Whitty, A. The resurgence of covalent drugs Nat. Rev. Drug Discovery 2011, 10, 307-317
22. Baell, J. B.; Holloway, G. A. New substructure filters for removal of Pan Assay Interference Compounds (PAINS) from screening libraries and for their exclusion in bioassays J. Med. Chem. 2010, 53, 2719-2740
23. Delano, W. L. The PyMOL Molecular Graphics System; http://www.pymol.org, 2002.