3D-QSAR CoMFA studies on sulfonamide inhibitors of the Rv3588c β-carbonic anhydrase from Mycobacterium tuberculosis and design of not yet synthesized new molecules

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 29, Issue 3, 2014, Pages 449-455

  Singh, Shalini ^a   Supuran, Claudiu T ^b  

^a BAREILLY COLLEGE   (India)

^b UNIVERSITY OF FLORENCE   (Italy)

Author keywords

3D QSAR CoMFA; Carbonic anhydrase inhibitor; MtCA 2; Mycobacterium tuberculosis; Sulfonamides

Indexed keywords

CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; RV3588C BETA CARBONIC ANHYDRASE; SULFONAMIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; ISOENZYME; SULFANILAMIDE DERIVATIVE;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; DRUG DESIGN; DRUG SCREENING; ENZYME INHIBITION; MYCOBACTERIUM TUBERCULOSIS; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ENZYMOLOGY; STATIC ELECTRICITY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; DRUG DESIGN; ISOENZYMES; MODELS, MOLECULAR; MYCOBACTERIUM TUBERCULOSIS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STATIC ELECTRICITY; SULFANILAMIDES;

EID: 84900836069     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2013.800059     Document Type: Article

References (29)

1. Supuran, CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-74.
2. Supuran CT. Therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-81.
3. Mincione F, Menabuoni L, Supuran CT. Clinical applications of the carbonic anhydrase inhibitors in ophthalmology. In: Supuran CT, Scozzafava A, Conway J, eds. Carbonic anhydrase, its inhibitors and activator. Boca Raton (FL): CRC Press; 2004.
4. Supuran, CT. Carbonic anhydrases: catalytic and inhibition mechanisms, distribution and physiological roles. In: Pacscas I, ed. Carbonic anhydrase and modulation of physiologic and pathologic process in the organism. Timisoara, Romania: Helicon; 1994.
5. Supuran CT, Scozzafava A, Casini A. Development of sulfonamide carbonic anhydrase inhibitors (CAIs). In: Supuran CT, Scozzafava A, Conway J, eds. Carbonic anhydrase, its inhibitors and activators. Boca Raton (FL): CRC Press; 2004.
6. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-89.
7. Covarrubias AS, Larsson AM, Hogbom M, et al. Structure and function of carbonic anhydrases from Mycobacterium tuberculosis. J Biol Chem 2005;280:18782-9.
8. Covarrubias AS, Bergfors T, Jones TA, Hogbom M. Structural mechanics of the pH-dependent activity of beta-carbonic anhydrase from Mycobacterium tuberculosis. J Biol Chem 2006;281:4993-9.
9. Nishimori I, Minakuchi T, Vullo D, et al. Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. J Med Chem 2009;52:3116-20.
10. Carta F, Maresca A, Covarrubias AS, et al. Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c. Bioorg Med Chem Lett 2009;19:6649-54.
11. Dye C. Doomsday postponed? Preventing and reversing epidemics of drug-resistant tuberculosis. Nat Rev Microbiol 2009;7:81-7.
12. Ginsberg AM. Emerging drugs for active tuberculosis. Semin Respir Crit Care Med 2008;29:552-9.
13. Showalter HD, Denny WA. A roadmap for drug discovery and its translation to small molecule agents in clinical development for tuberculosis treatment. Tuberculosis 2008;88:S3-17.
14. Tomioka H, Tatano Y, Yasumoto K, Shimizu T. Recent advances in antituberculous drug development and novel drug targets. Expert Rev Respir Med 2008;2:455-71.
15. Pai MP, Turpin RS, Garey KW. Association of fluconazole area under the concentration-time curve/MIC and dose/MIC ratios with mortality in nonneutropenic patients with candidemia. Antimicrob Agents Chemother 2007;51:35-9.
16. Bennett JE, Izumikawa K, Marr KA. Mechanism of increased fluconazole resistance in Candida glabrata during prophylaxis. Antimicrob Agents Chemother 2004;48:1773-7.
17. Tsai HF, Krol AA, Sarti K, Bennett JE. Candida glabrata PDR1, a transcriptional regulator of a pleiotropic drug resistance network, mediates azole resistance inclinical isolates and petite mutants. Antimicrob Agents Chemother 2006;50:1384-92.
18. Hanage WP, Fraser C, Tang J, et al. Hyper-recombination, diversity and antibiotic resistance in pneumococcus. Science 2009;324: 1454-7.
19. Saini L, Gupta SP, Kumar Satuluri VSA. QSAR study on some series of sodium and potassium channel blockers. Med Chem 2009; 5:570-6.
20. Singh S, Supuran CT. Chemometric QSAR modeling and in silico design of carbonic anhydrase inhibition of a coral secretory isoform by sulfonamide. Bioorg Med Chem 2013;21:495-1502.
21. Singh, S. A QSAR study on novel series of carbonic anhydrase inhibitors hCA IX tumor-associated (hypoxia). Med Chem 2012;8: 656-72.
22. Singh S, Supuran C T. QSARs on human carbonic anhydrase VA and VB inhibitors of some new not yet synthesized, substituted aromatic/heterocyclic sulphonamides as anti-obesity agent. J Enzyme Inhib Med Chem 2012;27:666-72.
23. Singh S. A comparative molecular field (CoMFA) studies on carbonic anhydrase inhibitor hCA IX-tumor-associated (hypoxia). Lett Drug Des Discov 2011;8:877-83.
24. Singh S, Singh S, Shukla, P. Modeling of novel HIV-1 protease inhibitors incorporating N-Aryl-oxazolidinone-5-carboxamides as P2 ligands using quantum chemical and topological finger print descriptors. Med Chem Res 2011;20:1556-65.
25. Singh S, Khadikar PV, Scozzafava A, Supuran, CT. QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software. J Enzyme Inhib Med Chem 2009;24:337-49.
26. Everitt B, Landau S, Leese M. Cluster analysis. London: Arnold Press; 2001.
27. BROOD (version 2.0.0), OpenEye Science Software, 3600 Cerrillos Road, Suite1107, Santa Fe, USA; 2010.
28. Geladi P. Notes on the history and nature of partial least squares (PLS) modeling. J Chemon 1988;2:231-46.
29. Cramer III RD, Bunce JD, Patterson DE. Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR. Quant Struct Act Relat 1988;7: 18-25.