Tags

Type your tag names separated by a space and hit enter

Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II.
Bioorg Med Chem Lett. 2011 Oct 01; 21(19):5892-6.BM

Abstract

A series of compounds incorporating regioisomeric phenylethynylbenzenesulfonamide moieties has been investigated for the inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII. Inhibition between the low nanomolar to the milliomolar range has been observed against them, with several low nanomolar and tumor-CA selective inhibitors detected. The position of the sulfamoyl group with respect to the alkyne functionality, and the nature of the moieties substituting the second aromatic ring were the principal structural features influencing CA inhibition. The para-sulfamoyl-substituted derivatives were effective inhibitors of CA IX and XII, the meta-substituted regioisomers of CA I, IX and XII, whereas the ortho-substituted sulfonamides were weak inhibitors of CA I, II and IX, but inhibited significantly CA XII.

Authors+Show Affiliations

University of Alberta, Faculty of Pharmacy, Edmonton, Alberta, Canada T6G 2N8.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21852133

Citation

Knaus, Edward E., et al. "Phenylethynylbenzenesulfonamide Regioisomers Strongly and Selectively Inhibit the Transmembrane, Tumor-associated Carbonic Anhydrase Isoforms IX and XII Over the Cytosolic Isoforms I and II." Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 19, 2011, pp. 5892-6.
Knaus EE, Innocenti A, Scozzafava A, et al. Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II. Bioorg Med Chem Lett. 2011;21(19):5892-6.
Knaus, E. E., Innocenti, A., Scozzafava, A., & Supuran, C. T. (2011). Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II. Bioorganic & Medicinal Chemistry Letters, 21(19), 5892-6. https://doi.org/10.1016/j.bmcl.2011.07.090
Knaus EE, et al. Phenylethynylbenzenesulfonamide Regioisomers Strongly and Selectively Inhibit the Transmembrane, Tumor-associated Carbonic Anhydrase Isoforms IX and XII Over the Cytosolic Isoforms I and II. Bioorg Med Chem Lett. 2011 Oct 1;21(19):5892-6. PubMed PMID: 21852133.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II. AU - Knaus,Edward E, AU - Innocenti,Alessio, AU - Scozzafava,Andrea, AU - Supuran,Claudiu T, Y1 - 2011/07/30/ PY - 2011/06/11/received PY - 2011/07/23/revised PY - 2011/07/25/accepted PY - 2011/8/20/entrez PY - 2011/8/20/pubmed PY - 2012/4/17/medline SP - 5892 EP - 6 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 21 IS - 19 N2 - A series of compounds incorporating regioisomeric phenylethynylbenzenesulfonamide moieties has been investigated for the inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII. Inhibition between the low nanomolar to the milliomolar range has been observed against them, with several low nanomolar and tumor-CA selective inhibitors detected. The position of the sulfamoyl group with respect to the alkyne functionality, and the nature of the moieties substituting the second aromatic ring were the principal structural features influencing CA inhibition. The para-sulfamoyl-substituted derivatives were effective inhibitors of CA IX and XII, the meta-substituted regioisomers of CA I, IX and XII, whereas the ortho-substituted sulfonamides were weak inhibitors of CA I, II and IX, but inhibited significantly CA XII. SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/21852133/Phenylethynylbenzenesulfonamide_regioisomers_strongly_and_selectively_inhibit_the_transmembrane_tumor_associated_carbonic_anhydrase_isoforms_IX_and_XII_over_the_cytosolic_isoforms_I_and_II_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(11)01036-5 DB - PRIME DP - Unbound Medicine ER -