Carbonic anhydrase inhibitors; Phosphoryl-sulfonamides - A new class of high affinity inhibitors of isozymes I and II

被引：13
作者：
Fenesan, I
Popescu, R
Scozzafava, A
Crucin, V
Mateiciuc, E
Bauer, R
Ilies, MA
Supuran, CT
机构：
[1] Univ Florence, Lab Chim Inorgan & Bioinorgan, I-50121 Florence, Italy
[2] Inst Chem Raluca Ripan, Lab Elementorgan Cpds, Cluj Napoca, Romania
[3] Univ Agr Sci & Vet Med, Fac Biotechnol, Dept Chem, Bucharest 71331, Romania
来源：
JOURNAL OF ENZYME INHIBITION | 2000年 / 15卷 / 03期
关键词：
carbonic anhydrase; isozymes I; II; phosphoryl sulfonamides; pK(a);
D O I：
10.3109/14756360009040690
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A series of phosphorylated aromatic:heterocyclic sulfonamides with the general formula ArSO2NHPO3H2 have been prepared by condensing ArSO2NH2 with phosphorus pentachloride, Followed by controlled hydrolysis in the presence of formic acid. The new derivatives generally act as stronger inhibitors of two carbonic anhydrase (CA) isozymes, CA I and CA II, as compared to the parent unsubstituted sulfonamides from which they were obtained. The inhibition mechanism by this new class of CA inhibitors, as well as structure activity correlations for the series of investigated derivatives, are also discussed.
引用
收藏
页码：297 / 310
页数：14
相关论文
共 56 条
[1]   Molecular recognition of protein-ligand complexes: Applications to drug design [J].
Babine, RE ;
Bender, SL .
CHEMICAL REVIEWS, 1997, 97 (05) :1359-1472
[2]  
BARTLETT PA, 1990, J ORG CHEM, V55, P8268
[3]   STRUCTURAL AND FUNCTIONAL DIFFERENCES BETWEEN CARBONIC-ANHYDRASE ISOENZYME-I AND ISOENZYME-II AS STUDIED BY SITE-DIRECTED MUTAGENESIS [J].
BEHRAVAN, G ;
JONASSON, P ;
JONSSON, BH ;
LINDSKOG, S .
EUROPEAN JOURNAL OF BIOCHEMISTRY, 1991, 198 (03) :589-592
[4]   Studies in chemotherapy. VII. A theory of the relation of structure to activity of sulfanilamide type compounds [J].
Bell, PH ;
Roblin, RO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2905-2917
[5]  
BERTINI I, 1982, STRUCT BOND, V48, P45
[6]   COBALT(II) AS A PROBE OF THE STRUCTURE AND FUNCTION OF CARBONIC-ANHYDRASE [J].
BERTINI, I ;
LUCHINAT, C .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (08) :272-279
[7]   CHARACTERIZATION OF COBALT(II) BOVINE CARBONIC-ANHYDRASE AND OF ITS DERIVATIVES [J].
BERTINI, I ;
CANTI, G ;
LUCHINAT, C ;
SCOZZAFAVA, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (15) :4873-4877
[8]  
BLACKBURN GM, 1985, EUR J BIOCHEM, V153, P533
[9]   Matrix metalloproteinase inhibitors in arthritis [J].
Bottomley, KM ;
Johnson, WH ;
Walter, DS .
JOURNAL OF ENZYME INHIBITION, 1998, 13 (02) :79-101
[10]   Carbonic anhydrase inhibitors .37. Novel classes of isozyme I and II inhibitors and their mechanism of action. Kinetic and spectroscopic investigations on native and cobalt-substituted enzymes [J].
Briganti, F ;
Pierattelli, R ;
Scozzafava, A ;
Supuran, CT .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1996, 31 (12) :1001-1010
123456