Evaluation of selenide, diselenide and selenoheterocycle derivatives as carbonic anhydrase I, II, IV, VII and IX inhibitors

被引:39
作者
Angeli, Andrea [1 ]
Tanini, Damiano [2 ]
Viglianisi, Caterina [2 ]
Panzella, Lucia [3 ]
Capperucci, Antonella [2 ]
Menichetti, Stefano [2 ]
Supuran, Claudiu T. [1 ]
机构
[1] Univ Firenze, NEUROFARBA Dept, Sez Sci Farmaceut, Via Ugo Schiff 6, I-50019 Florence, Italy
[2] Univ Firenze, Dept Chem Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy
[3] Univ Naples Federico II, Dept Chem Sci, Via Cintia 4, I-80126 Naples, Italy
关键词
Carbonic anhydrase; Inhibitors; Metalloenzymes; Selenium; Diselenides; Selenides; Selenoheterocycles; NITRIC-OXIDE SYNTHASE; OXIDATIVE STRESS; CATALYTIC-ACTIVITY; DRUG DISCOVERY; ISOZYME-IX; TIAZOFURIN; DEHYDROGENASE; SULFONAMIDES; ANTIOXIDANT; ANALOGS;
D O I
10.1016/j.bmc.2017.03.013
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 selenides, diselenides and organoselenoheterocycles were evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the human (h) isoforms hCA I, II, IV, VII and IX, involved in a variety of diseases among which glaucoma, retinitis pigmentosa, epilepsy, arthritis and tumors etc. These investigated compounds showed inhibitory action against these isoforms and some of them were selective for inhibiting the cytosolic over the membrane-bound isoforms, thus making them interesting leads for the development of isoform-selective inhibitors. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2518 / 2523
页数:6
相关论文
共 81 条
[21]   Oxidants, oxidative stress and the biology of ageing [J].
Finkel, T ;
Holbrook, NJ .
NATURE, 2000, 408 (6809) :239-247
[22]  
Flohé L, 2000, IUBMB LIFE, V49, P411
[23]   Synthesis, structure, and antiproliferative activity of selenophenfurin, an inosine 5'-monophosphate dehydrogenase inhibitor analogue of selenazofurin [J].
Franchetti, P ;
Cappellacci, L ;
AbuSheikha, G ;
Jayaram, HN ;
Gurudutt, VV ;
Sint, T ;
Schneider, BP ;
Jones, WD ;
Goldstein, BM ;
Perra, G ;
DeMontis, A ;
Loi, AG ;
LaColla, P ;
Grifantini, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (11) :1731-1737
[24]   Isosteric analogues of nicotinamide adenine dinucleotide derived from furanfurin, thiophenfurin, and selenophenfurin as mammalian inosine monophosphate dehydrogenase (type I and II) inhibitors [J].
Franchetti, P ;
Cappellacci, L ;
Perlini, P ;
Jayaram, HN ;
Butler, A ;
Schneider, BP ;
Collart, FR ;
Huberman, E ;
Grifantini, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (10) :1702-1707
[25]   FURANFURIN AND THIOPHENFURIN - 2 NOVEL TIAZOFURIN ANALOGS - SYNTHESIS, STRUCTURE, ANTITUMOR-ACTIVITY, AND INTERACTIONS WITH INOSINE MONOPHOSPHATE DEHYDROGENASE [J].
FRANCHETTI, P ;
CAPPELLACCI, L ;
GRIFANTINI, M ;
BARZI, A ;
NOCENTINI, G ;
YANG, HY ;
OCONNOR, A ;
JAYARAM, HN ;
CARRELL, C ;
GOLDSTEIN, BM .
JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (19) :3829-3837
[26]  
GOLDSTEIN BM, 1991, BLOOD, V78, P593
[27]  
Hatchett R J, 1994, J Physiol Pharmacol, V45, P55
[28]   PREFERENTIAL INHIBITION OF INDUCIBLE NITRIC-OXIDE SYNTHASE BY EBSELEN [J].
HATTORI, R ;
INOUE, R ;
SASE, K ;
EIZAWA, H ;
KOSUGA, K ;
AOYAMA, T ;
MASAYASU, H ;
KAWAI, C ;
SASAYAMA, S ;
YUI, Y .
EUROPEAN JOURNAL OF PHARMACOLOGY-MOLECULAR PHARMACOLOGY SECTION, 1994, 267 (02) :R1-R2
[29]   Carbonic anhydrase inhibitors. Inhibition of tumor-associated isozyme IX by halogenosulfanilamide and halogenophenylaminobenzolamide derivatives [J].
Ilies, MA ;
Vullo, D ;
Pastorek, J ;
Scozzafava, A ;
Ilies, M ;
Caproiu, MT ;
Pastorekova, S ;
Supuran, CT .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (11) :2187-2196
[30]  
ITO H, 1990, ANTICANCER RES, V10, P891