CP-MLR directed QSAR study of carbonic anhydrase inhibitors: sulfonamide and sulfamate inhibitors

Brij Sharma; Pradeep Pilania; Prithvi Singh; Susheela Sharma; Yenamandra Prabhakar

doi:10.2478/s11532-009-0073-4

Open Access Published by De Gruyter Open Access October 6, 2009

CP-MLR directed QSAR study of carbonic anhydrase inhibitors: sulfonamide and sulfamate inhibitors

Brij Sharma , Pradeep Pilania , Prithvi Singh , Susheela Sharma and Yenamandra Prabhakar

From the journal Open Chemistry

https://doi.org/10.2478/s11532-009-0073-4

Abstract

The inhibition activities of sulfonamide and sulfamate derivatives for human carbonic anhydrases have been quantitatively analyzed using DRAGON descriptors. QSAR models have been obtained through combinatorial protocol-multiple linear regression (CP-MLR) computational procedure. For the hCA I inhibition activity, a higher value of information content index of the 1-order neighborhood symmetry (IC1) and a lower value of the Moran autocorrelations, MATS2v and MATS1p, along with a lower number of sulfur atoms in a molecular structure (nRSR) is beneficial to the activity. A higher number of 5-membered rings (nR05), a bigger distance between nitrogen and sulfur T(N..S), and a higher value of van der Waals volume weighted descriptor (GATS6v), are helpful to improve the hCA II inhibition activity. For the inhibition of hpCA, a lower value of the descriptors Jhetv and PW5, and higher values of the eigenvalue sum from Z weighted distance matrix, SEigZ, the Moran autocorrelation of lag 8 weighted by atomic van der Waals volumes, MATS8v and the Moran autocorrelation of lag 4 weighted by atomic Sanderson electronegativities, MATS4e are favorable. The derived significant models in such descriptors may further be used to synthesize new potential compounds and to decipher the mode of their actions at molecular level.

Keywords: Quantitative structure-activity relationship (QSAR); Inhibition activities of sulfonamide and sulfamate derivatives for human carbonic anhydrases (hCA I and hCA II) and α-carbonic anhydrase from Helicobacter pylori (hpCA); Combinatorial protocol in multiple linear regression (CP-MLR) analysis; DRAGON descriptors

[1] C.T. Supuran, A. Scozzafava, J. Conway, Carbonic Anhydrase-Its Inhibitors and Activators (CRC Press: Boca Raton, FL, 2004) 1 10.1201/9780203475300.ch1Search in Google Scholar

[2] W.S. Sly, P.Y. Hu, Annu. Rev. Biochem. 64, 375 (1995) http://dx.doi.org/10.1146/annurev.bi.64.070195.00211110.1146/annurev.bi.64.070195.002111Search in Google Scholar PubMed

[3] S. Pastorekova, S. Parkkila, J. Pastorek, C.T. Supuran, J. Enzy. Inhibn. Med. Chem. 19, 199 (2004) http://dx.doi.org/10.1080/1475636041000168954010.1080/14756360410001689540Search in Google Scholar PubMed

[4] C.T. Supuran, A. Scozzafava, A. Casini, Med. Res. Rev. 23, 146 (2003) http://dx.doi.org/10.1002/med.1002510.1002/med.10025Search in Google Scholar PubMed

[5] A. Scozzafava, A. Mastrolorenzo, C.T. Supuran, Expert Opin. Ther. Pat. 14, 667 (2004) http://dx.doi.org/10.1517/13543776.14.5.66710.1517/13543776.14.5.667Search in Google Scholar

[6] J. Lehtonen et al., J. Biol. Chem. 279, 2719 (2004) http://dx.doi.org/10.1074/jbc.M30898420010.1074/jbc.M308984200Search in Google Scholar PubMed

[7] K. Fujikawa-Adachi, I. Nishimori, T. Taguchi, S. Onishi, J. Biol. Chem. 274, 21228 (1999) http://dx.doi.org/10.1074/jbc.274.30.2122810.1074/jbc.274.30.21228Search in Google Scholar PubMed

[8] K. Fujikawa-Adachi, I. Nishimori, T. Taguchi, S. Onishi, Genomics 61, 74 (1999) http://dx.doi.org/10.1006/geno.1999.593810.1006/geno.1999.5938Search in Google Scholar PubMed

[9] I. Nishimori et al., J. Med. Chem. 48, 7860 (2005) http://dx.doi.org/10.1021/jm050483n10.1021/jm050483nSearch in Google Scholar PubMed

[10] D. Vullo et al., J. Med. Chem. 47, 1272 (2004) http://dx.doi.org/10.1021/jm031057+10.1021/jm031057+Search in Google Scholar PubMed

[11] C.T. Supuran, Expert Opin. Ther. Pat. 13, 1545 (2003) http://dx.doi.org/10.1517/13543776.13.10.154510.1517/13543776.13.10.1545Search in Google Scholar

[12] A. Weber et al., J. Med. Chem. 47, 550 (2004) http://dx.doi.org/10.1021/jm030912m10.1021/jm030912mSearch in Google Scholar PubMed

[13] S. Pastorekova et al., Bioorg. Med. Chem. Lett. 14, 869 (2004) http://dx.doi.org/10.1016/j.bmcl.2003.12.02910.1016/j.bmcl.2003.12.029Search in Google Scholar PubMed

[14] D. Vullo et al., Bioorg. Med. Chem. Lett. 15, 971 (2005) http://dx.doi.org/10.1016/j.bmcl.2004.12.05210.1016/j.bmcl.2004.12.052Search in Google Scholar PubMed

[15] G. De Simone et al., Bioorg. Med. Chem. Lett. 15, 2315 (2005) http://dx.doi.org/10.1016/j.bmcl.2005.03.03210.1016/j.bmcl.2005.03.032Search in Google Scholar PubMed

[16] D. Vullo et al., Bioorg. Med. Chem. Lett. 15, 963 (2005) http://dx.doi.org/10.1016/j.bmcl.2004.12.05310.1016/j.bmcl.2004.12.053Search in Google Scholar PubMed

[17] E. Svastova et al., FEBS Lett. 577, 439 (2004) http://dx.doi.org/10.1016/j.febslet.2004.10.04310.1016/j.febslet.2004.10.043Search in Google Scholar PubMed

[18] A. Cecchi et al., J. Med. Chem. 48, 4834 (2005) http://dx.doi.org/10.1021/jm050107310.1021/jm0501073Search in Google Scholar PubMed

[19] V. Menchise et al., J. Med. Chem. 48, 5721 (2005) http://dx.doi.org/10.1021/jm050333c10.1021/jm050333cSearch in Google Scholar PubMed

[20] J. Krungkrai et al., Bioorg. Med. Chem. 13, 483 (2005) http://dx.doi.org/10.1016/j.bmc.2004.10.01510.1016/j.bmc.2004.10.015Search in Google Scholar PubMed

[21] A. Suarez Covarrubias et al., J. Biol. Chem. 280, 18782 (2005) http://dx.doi.org/10.1074/jbc.M41434820010.1074/jbc.M414348200Search in Google Scholar

[22] A. Suarez Covarrubias, T. Bergfors. T.A. Jones, M. Hogbom, J. Biol. Chem. 281, 4993 (2006) http://dx.doi.org/10.1074/jbc.M51075620010.1074/jbc.M510756200Search in Google Scholar

[23] T. Klengel et al., Curr. Biol. 15, 2021 (2005) http://dx.doi.org/10.1016/j.cub.2005.10.04010.1016/j.cub.2005.10.040Search in Google Scholar

[24] E.G. Mogensen et al., Eukaryot. Cell 5, 103 (2006) http://dx.doi.org/10.1128/EC.5.1.103-111.200610.1128/EC.5.1.103-111.2006Search in Google Scholar

[25] Y.S. Bahn, G.M. Cox, J.R. Perfect, J. Heitman, Curr. Biol. 15, 2013 (2005) http://dx.doi.org/10.1016/j.cub.2005.09.04710.1016/j.cub.2005.09.047Search in Google Scholar

[26] B.J. Marshall, J.R. Warren, Lancet 16, 1311 (1984) http://dx.doi.org/10.1016/S0140-6736(84)91816-610.1016/S0140-6736(84)91816-6Search in Google Scholar

[27] B.J. Marshall, Am. J. Gastroenterol. 89, S116 (1994) Search in Google Scholar

[28] J. Personnet et al., N. Engl. J. Med. 325, 1131 (1991) 10.1056/NEJM199110173251603Search in Google Scholar PubMed

[29] S.F. Moss, M.J. Blaser, Nat. Clin. Pract. Oncol. 2, 90 (2005) http://dx.doi.org/10.1038/ncponc008110.1038/ncponc0081Search in Google Scholar PubMed

[30] J. Kountouras, C. Zavos, D. Chatzopoulos, Hepatogastroenterology 52, 1305 (2005) Search in Google Scholar

[31] B.J Marshall, H.M. Windsor, Med. Clin. North Am. 89, 313 (2005) http://dx.doi.org/10.1016/j.mcna.2004.09.00110.1016/j.mcna.2004.09.001Search in Google Scholar PubMed

[32] R. O’Mahony, D. Vaira, J. Holton, C. Basset, Sci. Prog. 87, 269 (2004) http://dx.doi.org/10.3184/00368500478323848110.3184/003685004783238481Search in Google Scholar PubMed

[33] F. Megraud, B.J. Marshall, Gastroenterol. Clin. North Am. 29, 759 (2000) http://dx.doi.org/10.1016/S0889-8553(05)70145-X10.1016/S0889-8553(05)70145-XSearch in Google Scholar

[34] J.P. Gisbert, J.M. Pajares, Helicobacter. 10, 363 (2005) http://dx.doi.org/10.1111/j.1523-5378.2005.00324.x10.1111/j.1523-5378.2005.00324.xSearch in Google Scholar PubMed

[35] Y. Nakayama, D.Y. Grahm, Expert Rev. Anti-Infect. Ther. 2, 599 (2004) http://dx.doi.org/10.1586/14787210.2.4.59910.1586/14787210.2.4.599Search in Google Scholar PubMed

[36] F. Megraud, Drugs 64, 1893 (2004) http://dx.doi.org/10.2165/00003495-200464170-0000310.2165/00003495-200464170-00003Search in Google Scholar PubMed

[37] F. Loughlin, Expert Opin. Ther. Targets 7, 725 (2003) http://dx.doi.org/10.1517/14728222.7.6.72510.1517/14728222.7.6.725Search in Google Scholar PubMed

[38] G. Sachs et al., Physiology (Bethesda) 20, 429 (2005) 10.1152/physiol.00032.2005Search in Google Scholar PubMed

[39] E.A. Marcus, A.P. Moshfegh, G. Sachs, D.R. Scott, J. Bacteriol. 187, 729 (2005) http://dx.doi.org/10.1128/JB.187.2.729-738.200510.1128/JB.187.2.729-738.2005Search in Google Scholar PubMed PubMed Central

[40] F.N. Stahler, L. Ganter, K. Lederer, M. Kist, S. Bereswill, FEMS Immunol. Med. Microbiol. 44, 183 (2005) http://dx.doi.org/10.1016/j.femsim.2004.10.02110.1016/j.femsim.2004.10.021Search in Google Scholar PubMed

[41] I. Nishimori et al., J. Med. Chem. 49, 2117 (2006) http://dx.doi.org/10.1021/jm051260010.1021/jm0512600Search in Google Scholar PubMed

[42] R. Todeschini, V. Consonni, A. Mauri, M. Pavan, DRAGON software version 3.0-2003, Milano (Italy) Search in Google Scholar

[43] ChemDraw Ultra 6.0 and Chem3D Ultra, Cambridge Soft Corporation: Cambridge, USA Search in Google Scholar

[44] Y.S. Prabhakar, QSAR Comb. Sci. 22, 583 (2003) http://dx.doi.org/10.1002/qsar.20033081410.1002/qsar.200330814Search in Google Scholar

[45] Y.S. Prabhakar, V.R. Solomon, R.K. Rawal, M.K. Gupta, S.B. Katti, QSAR Comb. Sci. 23, 234 (2004) http://dx.doi.org/10.1002/qsar.20033085410.1002/qsar.200330854Search in Google Scholar

[46] Y.S. Prabhakar, Internet Electron. J. Mol. Des. 3, 150 (2004) Search in Google Scholar

[47] M.K. Gupta, R. Sagar, A.K. Shaw, Y.S. Prabhakar, Bioorg. Med. Chem. 13, 343 (2005) http://dx.doi.org/10.1016/j.bmc.2004.10.02510.1016/j.bmc.2004.10.025Search in Google Scholar

[48] S. Sharma, Y.S. Prabhakar, P. Singh, B.K. Sharma, Euro. J. Med. Chem. 43, 2354 (2008) http://dx.doi.org/10.1016/j.ejmech.2008.01.02010.1016/j.ejmech.2008.01.020Search in Google Scholar

[49] S.S. So, M. Karplus, J. Med. Chem. 40, 4347 (1997) http://dx.doi.org/10.1021/jm970487v10.1021/jm970487vSearch in Google Scholar

[50] Y.S. Prabhakar, R.K. Rawal, M.K. Gupta, V.R. Solomon, S.B. Katti, Comb. Chem. High Through. Screen. 8, 431 (2005) http://dx.doi.org/10.2174/138620705454653110.2174/1386207054546531Search in Google Scholar

[51] H. Akaike, In: B.N. Petrov, F. Csaki (Eds.), Second international symposium on information theory (Akademiai Kiado Budapest, 1973) 267 Search in Google Scholar

[52] H. Akaike, IEEE Trans Autom. Control AC-19, 716 (1974) http://dx.doi.org/10.1109/TAC.1974.110070510.1109/TAC.1974.1100705Search in Google Scholar

[53] H. Kubinyi, Quant. Struct.-Act. Relat. 13, 285 (1994) Search in Google Scholar

[54] H. Kubinyi, Quant. Struct.-Act. Relat. 13, 393 (1994) Search in Google Scholar

[55] J. Friedman, Technical Report No 102, Laboratory for computational statistics (Stanford University, Stanford, 1990) Search in Google Scholar

[56] R.L. Lipnick, Sci. Total Environ. 109, 131 (1991) http://dx.doi.org/10.1016/0048-9697(91)90175-E10.1016/0048-9697(91)90175-ESearch in Google Scholar

[57] J. Devillers, R.L. Lipnick, In: K. Karcher, J. Devillers (Eds.), Practical applications of quantitative structure-activity relationships (QSAR) in environemntal chemistry and toxicology (Kluwer, Dordrecht, 1990) 129 Search in Google Scholar

Published Online: 2009-10-6

Published in Print: 2009-12-1

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

CP-MLR directed QSAR study of carbonic anhydrase inhibitors: sulfonamide and sulfamate inhibitors

Abstract

Journal and Issue

Articles in the same Issue