Salicylanilide Diethyl Phosphates as Potential Inhibitors of Some Mycobacterial Enzymes

Scientific World Journal

Volumn 2014, Issue , 2014, Pages

  Krátký, Martin ^a   Novotná, Eva ^a   Saxena, Shalini ^b   Yogeeswari, Perumal ^b   Sriram, Dharmarajan ^b   Švarcová, Markéta ^a   Vinšová, Jarmila ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DEHYDROGENASE; ANTIMYCOBACTERIAL AGENT; BACTERIAL ENZYME; CHORISMATE MUTASE; ENZYME INHIBITOR; ISOCITRATE LYASE; LYSINE 6 AMINOTRANSFERASE; PANTOTHENATE SYNTHETASE; PHOSPHATE; SALICYLANILIDE DERIVATIVE; SALICYLANILIDE DIETHYL PHOSPHATE DERIVATIVE; SYNTHETASE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; TUBERCULOSTATIC AGENT;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL GROWTH; CRYSTAL STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME STRUCTURE; ESTERIFICATION; EVALUATION STUDY; IC50; IN VITRO STUDY; MOLECULAR DOCKING; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; ANTAGONISTS AND INHIBITORS; CHEMISTRY; ENZYMOLOGY;

MYCOBACTERIUM TUBERCULOSIS;

ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; ENZYME INHIBITORS; MOLECULAR DOCKING SIMULATION; MYCOBACTERIUM TUBERCULOSIS; SALICYLANILIDES;

EID: 84934929146     PISSN: 23566140     EISSN: 1537744X     Source Type: Journal    
DOI: 10.1155/2014/703053     Document Type: Article

References (24)

1. B. Saifullah, P. Arulselvan, M. E. El Zowalaty et al., "Development of a highly biocompatible antituberculosis nanodelivery formulation based on para-aminosalicylic acidizinc layered hydroxide nanocomposites", The Scientific World Journal, vol. 2014, Article ID401460, 12 pages, 2014.
2. J. Vinísová, J. Kozic, M. Krátký et al., "Salicylanilide diethyl phosphates: synthesis, antimicrobial activity and cytotoxicity", Bioorganic and Medicinal Chemistry, vol. 22, no. 2, pp. 728-737, 2014.
3. M. Krátký, J. Vinšová, E. Novotná et al., "Salicylanilide derivatives block Mycobacterium tuberculosis through inhibition of isocitrate lyase and methionine aminopeptidase", Tuberculosis, vol. 92, no. 5, pp. 434-439, 2012.
4. S. K. Hatzios and C. R. Bertozzi, "The regulation of sulfur metabolism in Mycobacterium tuberculosis", PLoS Pathogens, vol. 7, no. 7, Article IDe1002036, 8 pages, 2011.
5. M. Krátký, J. Vinšová, E. Novotná, J. Mandíková, F. Trejtnar, and J. Stolaříková, "Antibacterial activity of salicylanilide 4-(trifluoromethyl) benzoates", Molecules, vol. 18, no. 4, pp. 3674-3688, 2013.
6. A. B. Andersen, P. Andersen, and L. Ljungqvist, "Structure and function of a 40, 000-molecular-weight protein antigen of Mycobacterium tuberculosis", Infection and Immunity, vol. 60, no. 6, pp. 2317-2323, 1992.
7. Z. Y. Feng, N. E. Cáceres, G. Sarath, and R. G. Barletta, "Mycobacterium smegmatis L-alanine dehydrogenase (Ald) is required for proficient utilization of alanine as a sole nitrogen source and sustained anaerobic growth", Journal of Bacteriology, vol. 184, no. 18, pp. 5001-5010, 2002.
8. B. Ling, M. Sun, S. Bi, Z. Jing, and Y. Liu, "Molecular dynamics simulations of the coenzyme induced conformational changes of Mycobacterium tuberculosis L-alanine dehydrogenase", Journal of Molecular Graphics and Modelling, vol. 35, pp. 1-10, 2012.
9. J. C. Betts, P. T. Lukey, L. C. Robb, R. A. McAdam, and K. Duncan, "Evaluation of a nutrient starvation model of Mycobacterium tuberculosis persistence by gene and protein expression profiling", Molecular Microbiology, vol. 43, no. 3, pp. 717-731, 2002.
10. D. Dube, S. M. Tripathi, and R. Ramachandran, "Identification of in vitro inhibitors of Mycobacterium tuberculosis Lysine ε-aminotransferase by pharmacophore mapping and three-dimensional flexible searches", Medicinal Chemistry Research, vol. 17, no. 2-7, pp. 182-188, 2008.
11. M. I. Voskuil, K. C. Visconti, and G. K. Schoolnik, "Mycobacterium tuberculosis gene expression during adaptation to stationary phase and low-oxygen dormancy", Tuberculosis, vol. 84, no. 3-4, pp. 218-227, 2004.
12. M. Okvist, R. Dey, S. Sasso, E. Grahn, P. Kast, and U. Krengel, "1.6 Å crystal structure of the secreted chorismate mutase from Mycobacteriumtuberculosis: novel fold topology revealed", Journal of Molecular Biology, vol. 357, no. 5, pp. 1483-1499, 2006.
13. E. L. White, K. Southworth, L. Ross et al., "A novel inhibitor of Mycobacteriumtuberculosis pantothenate synthetase", Journal of Biomolecular Screening, vol. 12, no. 1, pp. 100-105, 2007.
14. Y. Yang, P. Gao, Y. Liu et al., "A discovery of novel Mycobacterium tuberculosis pantothenate synthetase inhibitors based on the molecular mechanism of actinomycin D inhibition", Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 13, pp. 3943-3946, 2011.
15. G. H. Dixon and H. L. Kornberg, "Assay methods for key enzymes of the glyoxylate cycle", Biochemical Journal, vol. 72, p. P3, 1959.
16. S. M. Tripathi and R. Ramachandran, "Crystal structures of the Mycobacterium tuberculosis secretory antigen alanine dehydrogenase (Rv2780) in apo and ternary complex forms captures "open" and "closed" enzyme conformations", Proteins: Structure, Function and Genetics, vol. 72, no. 3, pp. 1089-1095, 2008.
17. S. M. Tripathi and R. Ramachandran, "Overexpression, purification, crystallization and preliminary X-ray analysis of Rv2780 from Mycobacterium tuberculosis H37Rv", Acta Crystallographica Section F: Structural Biology and Crystallization Communications, vol. 64, no. 5, pp. 367-370, 2008.
18. S. M. Tripathi and R. Ramachandran, "Overexpression, purification and crystallization of lysine ε-aminotransferase (Rv3290c) from Mycobacterium tuberculosis H37Rv", Acta Crystallographica F: Structural Biology and Crystallization Communications, vol. 62, no. 6, pp. 572-575, 2006.
19. R. Adepu, K. S. Kumar, and S. Sandra, "C-N bond formation under Cu-catalysis: synthesis and in vitro evaluation of N-aryl substituted thieno[2, 3-d]pyrimidin-4 (3H)-ones against chorismate mutase", Bioorganic and Medicinal Chemistry, vol. 20, no. 17, pp. 5127-5138, 2012.
20. G. Samala, P. B. Devi, R. Nallangi, P. Yogeeswari, and D. Sriram, "Development of 3-phenyl-4, 5, 6, 7-tetrahydro-1H-pyrazolo[4, 3-c]pyridine derivatives as novel Mycobacterium tuberculosis pantothenate synthetase inhibitors", European Journal of Medicinal Chemistry, vol. 69, pp. 356-364, 2013.
21. S. Wang and D. Eisenberg, "Crystal structures of a pantothenate synthetase from M. tuberculosis and its complexes with substrates and a reaction intermediate", Protein Science, vol. 12, no. 5, pp. 1097-1108, 2003.
22. E. F. Pettersen, T. D. Goddard, C. C. Huang et al., "UCSF Chimeraía visualization system for exploratory research and analysis", Journal of Computational Chemistry, vol. 25, no. 13, pp. 1605-1612, 2004.
23. O. Trott and A. J. Olson, "Software news and update Auto Dock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading", Journal of Computational Chemistry, vol. 31, no. 2, pp. 455-461, 2010.
24. The Py Mol Molecular Graphics System, "Version 1.1r1, Schrödinger, LLC", http://www.pymol.org.