Tags

Type your tag names separated by a space and hit enter

Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors.
J Enzyme Inhib Med Chem. 2017 Dec; 32(1):1274-1281.JE

Abstract

A series of curcumin inspired sulfonamide derivatives was prepared from various chalcones and 4-sulfamoyl benzaldehyde via Claisen-Schmidt condensation. All new compounds were assayed as inhibitors of four human isoforms of the metalloenzyme carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. Interesting inhibitory activities were observed against all these isoforms. hCA I, an isoform involved in several eye diseases was inhibited moderately with KIs in the range of 191.8-904.2 nM, hCA II, an antiglaucoma drug target was highly inhibited by the new sulfonamides, with KIs in the range of 0.75-8.8 nM. hCA IX, a tumor-associated isoform involved in cancer progression and metastatic spread was potently inhibited by the new sulfonamides, with KIs in the range of 2.3-87.3 nM, whereas hCA XII, and antiglaucoma and anticancer drug target, was inhibited with KIs in the range of 6.1-71.8 nM. It is noteworthy that one of the new compounds, 5d, was found to be almost 9 times more selective against hCA II (KI = 0.89 nM) over hCA IX and hCA XII, whereas 5e was 3 and 70 times more selective against hCA II (KI = 0.75 nM) over hCA IX and hCA XII, respectively.

Authors+Show Affiliations

a Department of Medicinal Chemistry , National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad , India.a Department of Medicinal Chemistry , National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad , India.b NEUROFARBA Department , Università degli Studi di Firenze, Sezione di Scienze Farmaceutiche , Florence , Italy.a Department of Medicinal Chemistry , National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad , India.a Department of Medicinal Chemistry , National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad , India.a Department of Medicinal Chemistry , National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad , India.b NEUROFARBA Department , Università degli Studi di Firenze, Sezione di Scienze Farmaceutiche , Florence , Italy.a Department of Medicinal Chemistry , National Institute of Pharmaceutical Education and Research (NIPER) , Hyderabad , India.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28965419

Citation

Ramya, P V Sri, et al. "Discovery of Curcumin Inspired Sulfonamide Derivatives as a New Class of Carbonic Anhydrase Isoforms I, II, IX, and XII Inhibitors." Journal of Enzyme Inhibition and Medicinal Chemistry, vol. 32, no. 1, 2017, pp. 1274-1281.
Ramya PVS, Angapelly S, Angeli A, et al. Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors. J Enzyme Inhib Med Chem. 2017;32(1):1274-1281.
Ramya, P. V. S., Angapelly, S., Angeli, A., Digwal, C. S., Arifuddin, M., Babu, B. N., Supuran, C. T., & Kamal, A. (2017). Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 1274-1281. https://doi.org/10.1080/14756366.2017.1380638
Ramya PVS, et al. Discovery of Curcumin Inspired Sulfonamide Derivatives as a New Class of Carbonic Anhydrase Isoforms I, II, IX, and XII Inhibitors. J Enzyme Inhib Med Chem. 2017;32(1):1274-1281. PubMed PMID: 28965419.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Discovery of curcumin inspired sulfonamide derivatives as a new class of carbonic anhydrase isoforms I, II, IX, and XII inhibitors. AU - Ramya,P V Sri, AU - Angapelly,Srinivas, AU - Angeli,Andrea, AU - Digwal,Chander Singh, AU - Arifuddin,Mohammed, AU - Babu,Bathini Nagendra, AU - Supuran,Claudiu T, AU - Kamal,Ahmed, PY - 2017/10/3/entrez PY - 2017/10/3/pubmed PY - 2017/10/11/medline KW - Carbonic anhydrase KW - curcumin KW - isoforms I, II, IX and XII KW - sulfonamide SP - 1274 EP - 1281 JF - Journal of enzyme inhibition and medicinal chemistry JO - J Enzyme Inhib Med Chem VL - 32 IS - 1 N2 - A series of curcumin inspired sulfonamide derivatives was prepared from various chalcones and 4-sulfamoyl benzaldehyde via Claisen-Schmidt condensation. All new compounds were assayed as inhibitors of four human isoforms of the metalloenzyme carbonic anhydrase (hCA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. Interesting inhibitory activities were observed against all these isoforms. hCA I, an isoform involved in several eye diseases was inhibited moderately with KIs in the range of 191.8-904.2 nM, hCA II, an antiglaucoma drug target was highly inhibited by the new sulfonamides, with KIs in the range of 0.75-8.8 nM. hCA IX, a tumor-associated isoform involved in cancer progression and metastatic spread was potently inhibited by the new sulfonamides, with KIs in the range of 2.3-87.3 nM, whereas hCA XII, and antiglaucoma and anticancer drug target, was inhibited with KIs in the range of 6.1-71.8 nM. It is noteworthy that one of the new compounds, 5d, was found to be almost 9 times more selective against hCA II (KI = 0.89 nM) over hCA IX and hCA XII, whereas 5e was 3 and 70 times more selective against hCA II (KI = 0.75 nM) over hCA IX and hCA XII, respectively. SN - 1475-6374 UR - https://www.unboundmedicine.com/medline/citation/28965419/Discovery_of_curcumin_inspired_sulfonamide_derivatives_as_a_new_class_of_carbonic_anhydrase_isoforms_I_II_IX_and_XII_inhibitors_ L2 - http://www.tandfonline.com/doi/full/10.1080/14756366.2017.1380638 DB - PRIME DP - Unbound Medicine ER -