Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I, II, III, VII and XIII with less investigated inorganic anions

被引:33
作者
Innocenti, Alessio [1 ]
Scozzafava, Andrea [1 ]
Supuran, Claudiu T. [1 ]
机构
[1] Univ Florence, Lab Chim Bioinorgan, I-50019 Florence, Italy
基金
欧盟第七框架计划;
关键词
Carbonic anhydrase; Isoform I; II; III; VIII; XIII; Inorganic anion; Trithiocarbonate; Zinc-binding group; Dithiocarbamates; ISOZYME-II; X-RAY; ANTITUMOR SULFONAMIDE; SECRETORY ISOFORM; CRYSTAL-STRUCTURE; TRITHIOCARBONATES; TRANSMEMBRANE; SELECTIVITY; THIOXOLONE; AFFINITY;
D O I
10.1016/j.bmcl.2009.02.088
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
An inhibition study of the cytosolic carbonic anhydrase (CA, EC 4.2.1.1) isoforms I, II, III, VII and XIII with anions such as stannate(IV), selenate(VI), tellurate(VI), perosmate(VIII), persulfate, pyrophosphate(V), pyrovanadate(V), tetraborate, persulfate, perrhenate(VII), perrutenate(VII), selenocyanate, iminodisulfonate,. fluorosulfate and trithiocarbonate is reported. Trithiocarbonate was the best inhibitor detected, showing affinities of 8.7-9.9 mu M for CA I-III, of 36.15 mM for CA VII and of 0.43 mM for CA XIII. Considering trithiocarbonate as lead, we show that compounds incorporating the new zinc-binding group CS2-, such as among other the dithiocarbamates, are even more active inhibitors, with submicromolar inhibitory activity. New classes of CA inhibitors are being detected based on the CS2- zinc-binding group. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1855 / 1857
页数:3
相关论文
共 50 条
[21]   Inhibition of carbonic anhydrase isoforms I, II, IX and XII with novel Schiff bases: Identification of selective inhibitors for the tumor-associated isoforms over the cytosolic ones [J].
Sarikaya, Busra ;
Ceruso, Mariangela ;
Carta, Fabrizio ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (21) :5883-5890
[22]   Carbonic anhydrase inhibitors: in vitro inhibition of α isoforms (hCA I, hCA II, bCA III, hCA IV) by flavonoids [J].
Ekinci, Derya ;
Karagoz, Lutfi ;
Ekinci, Deniz ;
Senturk, Murat ;
Supuran, Claudiu T. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2013, 28 (02) :283-288
[23]   Inhibition pattern of sulfamide-related compounds in binding to carbonic anhydrase isoforms I, II, VII, XII and XIV [J].
Gavernet, Luciana ;
Gonzalez Funes, Jose L. ;
Palestro, Pablo H. ;
Bruno Blanch, Luis E. ;
Estiu, Guillermina L. ;
Maresca, Alfonso ;
Barrios, Ivana ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (06) :1410-1418
[24]   Phenylethynylbenzenesulfonamide regioisomers strongly and selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic isoforms I and II [J].
Knaus, Edward E. ;
Innocenti, Alessio ;
Scozzafava, Andrea ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (19) :5892-5896
[25]   Indapamide-like benzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, and XIII [J].
Capkauskaite, Edita ;
Baranauskiene, Lina ;
Golovenko, Dmitrij ;
Manakova, Elena ;
Grazulis, Saulius ;
Tumkevicius, Sigitas ;
Matulis, Daumantas .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (21) :7357-7364
[26]   Inhibition of carbonic anhydrase isoforms I, II, IV, VII and XII with carboxylates and sulfonamides incorporating phthalimide/phthalic anhydride scaffolds [J].
El-Azab, Adel S. ;
Abdel-Aziz, Alaa A. -M. ;
Ayyad, Rezk R. ;
Ceruso, Mariangela ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (01) :20-25
[27]   Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors [J].
Angapelly, Srinivas ;
Ramya, P. V. Sri ;
Angeli, Andrea ;
Del Prete, Sonia ;
Capasso, Clemente ;
Arifuddin, Mohammed ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (20) :5726-5732
[28]   Inhibition Studies on Carbonic Anhydrase Isoforms I, II, IX, and XII with a Series of Sulfaguanidines [J].
Abdoli, Morteza ;
De Luca, Viviana ;
Capasso, Clemente ;
Supuran, Claudiu T. ;
Zalubovskis, Raivis .
CHEMMEDCHEM, 2023, 18 (06)
[29]   Carbonic anhydrase inhibitors. Inhibition of transmembrane isozymes XII (cancer-associated) and XIV with anions [J].
Innocenti, Alessio ;
Vullo, Daniela ;
Pastorek, Jaromir ;
Scozzafava, Andrea ;
Pastorekova, Silvia ;
Nishimori, Isao ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (06) :1532-1537
[30]   Carbonic anhydrase inhibitors: Synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety [J].
Sethi, Kalyan K. ;
Vullo, Daniella ;
Verma, Saurabh M. ;
Tanc, Muhammet ;
Carta, Fabrizio ;
Supuran, Claudiu T. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (19) :5973-5982