Carbonic anhydrase inhibitors. Inhibition of the β-class enzymes from the fungal pathogens Candida albicans and Cryptococcus neoformans with branched aliphatic/aromatic carboxylates and their derivatives

被引：25

作者：

Carta, Fabrizio ^{[1
]}

Innocenti, Alessio ^{[1
]}

Hall, Rebecca A. ^{[2
]}

Muehlschlegel, Fritz A. ^{[2
]}

Scozzafava, Andrea ^{[1
]}

Supuran, Claudiu T. ^{[1
]}

机构：

[1] Univ Florence, Lab Chim Bioinorgan, I-50019 Florence, Italy

[2] Univ Kent, Sch Biosci, Canterbury CT2 7NJ, Kent, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 08期

基金：

英国生物技术与生命科学研究理事会;

关键词：

Carbonic anhydrase; Carboxylate; Inhibitor; beta-Class enzyme; Antifungals; Candida albicans; Cryptococcus neoformans; YEAST SACCHAROMYCES-CEREVISIAE; MYCOBACTERIUM-TUBERCULOSIS; DRUG TARGETS; GAMMA-CLASS; CO2; COUMARINS; ANIONS; IDENTIFICATION; SULFONAMIDES; ACTIVATORS;

D O I：

10.1016/j.bmcl.2011.02.057

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The inhibition of the beta-carbonic anhydrases (CAs, EC 4.2.1.1) from the pathogenic fungi Cryptococcus neoformans (Can2) and Candida albicans (Nce103) with a series of 25 branched aliphatic and aromatic carboxylates has been investigated. Human isoforms hCA I and II were also included in the study for comparison. Aliphatic carboxylates were generally millimolar hCA I and II inhibitors and low micromolar/submicromolar beta-CA inhibitors. Aromatic carboxylates were micromolar inhibitors of the four enzymes but some of them showed low nanomolar activity against the fungal pathogenic enzymes. 4-Hydroxy-and 4-methoxy-benzoate inhibited Can2 with K(I)s of 9.5-9.9 nM. The methyl esters, hydroxamates, hydrazides and carboxamides of some of these derivatives were also effective inhibitors of the alpha- and beta-CAs investigated here. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2521 / 2526

页数：6

共 16 条

[1] Carbonic anhydrase inhibitors. Inhibition of the β-class enzymes from the fungal pathogens Candida albicans and Cryptococcus neoformans with aliphatic and aromatic carboxylates
Innocenti, Alessio
Hall, Rebecca A.
Schlicker, Christine
Muehlschlegel, Fritz A.
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (07) : 2654 - 2657
[2] Carbonic anhydrase inhibitors:: Inhibition of the β-class enzymes from the fungal pathogens Candida albicans and Cryptococcus neoformans with simple anions
Innocenti, Alessio
Muehlschlegel, Fritz A.
Hall, Rebecca A.
Steegborn, Clemens
Scozzafava, Andrea
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (18) : 5066 - 5070
[3] Carbonic anhydrase inhibitors. Inhibition of the fungal β-carbonic anhydrases from Candida albicans and Cryptococcus neoformans with boronic acids
Innocenti, Alessio
Winum, Jean-Yves
Hall, Rebecca A.
Muehlschlegel, Fritz A.
Scozzafava, Andrea
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (10) : 2642 - 2645
[4] Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal β-carbonic anhydrase from Candida albicans with sulfonamides
Innocenti, Alessio
Hall, Rebecca A.
Schlicker, Christine
Scozzafava, Andrea
Steegborn, Clemens
Muehlschlegel, Fritz A.
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (13) : 4503 - 4509
[5] Carbonic anhydrase inhibitors. The β-carbonic anhydrases from the fungal pathogens Cryptococcus neoformans and Candida albicans are strongly inhibited by substituted-phenyl-1H-indole-5-sulfonamides
Guzel, Ozlen
Maresca, Alfonso
Hall, Rebecca A.
Scozzafava, Andrea
Mastrolorenzo, Antonio
Muhlschlegel, Fritz A.
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (08) : 2508 - 2511
[6] Dithiocarbamates are strong inhibitors of the beta-class fungal carbonic anhydrases from Cryptococcus neoformans, Candida albicans and Candida glabrata
Monti, Simona Maria
Maresca, Alfonso
Viparelli, Francesca
Carta, Fabrizio
De Simone, Giuseppina
Muehlschlegel, Fritz A.
Scozzafava, Andrea
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) : 859 - 862
[7] Carbonic anhydrase inhibitors. Inhibition of the β-class enzyme from the pathogenic yeast Candida glabrata with anions
Innocenti, Alessio
Leewattanapasuk, Worraanong
Muehlschlegel, Fritz A.
Mastrolorenzo, Antonio
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (16) : 4802 - 4805
[8] Carbonic anhydrase activators: Activation of the β-carbonic anhydrases from the pathogenic fungi Candida albicans and Cryptococcus neoformans with amines and amino acids
Innocenti, Alessio
Hall, Rebecca A.
Scozzafava, Andrea
Muehlschlegel, Fritz A.
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (03) : 1034 - 1037
[9] Carbonic anhydrase inhibitors.: Inhibition of the prokariotic beta and gamma-class enzymes from Archaea with sulfonamides
Zimmerman, S
Innocenti, A
Casini, A
Ferry, JG
Scozzafava, A
Supuran, CT
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (24) : 6001 - 6006
[10] Carbonic anhydrase inhibitors. Inhibition of the β-class enzyme from the yeast Saccharomyces cerevisiae with anions
Isik, Semra
Kockar, Feray
Arslan, Oktay
Guler, Ozen Ozensoy
Innocenti, Alessio
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (24) : 6327 - 6331

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