Organoruthenium(II) complexes of acetazolamide potently inhibit human carbonic anhydrase isoforms I, II, IX and XII

被引：18

作者：

Sersen, Sara ^{[1
]}

Traven, Katja ^{[1
]}

Kljun, Jakob ^{[1
]}

Turel, Iztok ^{[1
]}

Supuran, Claudiu T. ^{[2
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113, SI-1000 Ljubljana, Slovenia

[2] Univ Firenze, Dipartimento Neurofarba, Sez Sci Farmaceut & Nutraceut, Via U Schiff 6, I-50019 Florence, Italy

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2019年 / 34卷 / 01期

关键词：

Carbonic anhydrase; human isoforms; acetazolamide; Ru(II); metal complex; CRYSTAL-STRUCTURE; RUTHENIUM COMPLEXES; ISOZYME-II; HETEROCYCLIC SULFONAMIDES; COORDINATION-COMPOUNDS; BIOLOGICAL EVALUATION; PATENT; ANTIFUNGAL; DRUGS; ANTIBACTERIAL;

D O I：

10.1080/14756366.2018.1547288

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：

Two acetazolamide (AAZ) complexes with ruthenium(II) eta(6)-p-cymene chloride were synthesised, characterised and tested for their inhibitory effects on several carbonic anhydrase (CA, EC 4.2.1.1) isoforms with pharmacological applications. Against human (h) isoform hCA I, the two complexes showed inhibition constants in the range of 8.5-23.4 nM (AAZ has a K-I of 250 nM), against hCA II of 0.48-4.2 nM, whereas against hCA IX of 0.63-3.8 nM and against hCA XII of 0.04-0.52 nM, respectively. These highly effective ruthenium acetazolamide derivatives against the tumour-associated CA isoforms IX and XII warrant further in vivo studies, in hypoxic tumours overexpressing these enzymes.

引用

页码：388 / 393

页数：6

共 85 条

[1] Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrases and steroid sulfatase [J].

Abbate, F ;

Winum, JY ;

Potter, BVL ;

Casini, A ;

Montero, JL ;

Scozzafava, A ;

Supuran, CT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (01) :231-234

[2] Multiple Binding Modes of Inhibitors to Carbonic Anhydrases: How to Design Specific Drugs Targeting 15 Different Isoforms? [J].

Alterio, Vincenzo ;

Di Fiore, Anna ;

D'Ambrosio, Katia ;

Supuran, Claudiu T. ;

De Simone, Giuseppina .

CHEMICAL REVIEWS, 2012, 112 (08) :4421-4468

[3]

ANDRUH M, 1991, REV ROUM CHIM, V36, P727

[4] Versatile coordination of acetazolamide to ruthenium(II) p-cymene complexes and preliminary cytotoxicity studies [J].

Biancalana, Lorenzo ;

Batchelor, Lucinda K. ;

Ciancaleoni, Gianluca ;

Zacchini, Stefano ;

Pampaloni, Guido ;

Dyson, Paul J. ;

Marchetti, Fabio .

DALTON TRANSACTIONS, 2018, 47 (28) :9367-9384

[5]

Borrás J, 2004, CRC ENZYM INHIB SER, P183

[6] Carbonic anhydrase inhibitors: Synthesis of water-soluble, topically effective intraocular pressure lowering aromatic/heterocyclic sulfonamides containing 8-quinoline-sulfonyl moieties: Is the tail more important than the ring? [J].

Borras, J ;

Scozzafava, A ;

Menabuoni, L ;

Mincione, F ;

Briganti, F ;

Mincione, G ;

Supuran, CT .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (11) :2397-2406

[7]

Borras J, 1996, Met Based Drugs, V3, P143, DOI 10.1155/MBD.1996.143

[8] Addition of carbonic anhydrase 9 inhibitor SLC-0111 to temozolomide treatment delays glioblastoma growth in vivo [J].

Boyd, Nathaniel H. ;

Walker, Kiera ;

Fried, Joshua ;

Hackney, James R. ;

McDonald, Paul C. ;

Benavides, Gloria A. ;

Spina, Raffaella ;

Audia, Alessandra ;

Scott, Sarah E. ;

Libby, Catherine J. ;

Anh Nhat Tran ;

Bevensee, Mark O. ;

Griguer, Corinne ;

Nozell, Susan ;

Gillespie, G. Yancey ;

Nabors, Burt ;

Bhat, Krishna P. ;

Bar, Eli E. ;

Darley-Usmar, Victor ;

Xu, Bo ;

Gordon, Emily ;

Cooper, Sara J. ;

Dedhar, Shoukat ;

Hjelmeland, Anita B. .

JCI INSIGHT, 2017, 2 (24)

[9] Discovery of 4-Hydroxy-3-(3-(phenylureido)benzenesulfonamides as SLC-0111 Analogues for the Treatment of Hypoxic Tumors Overexpressing Carbonic Anhydrase IX [J].

Bozdag, Murat ;

Carta, Fabrizio ;

Ceruso, Mariangela ;

Ferraroni, Marta ;

McDonald, Paul C. ;

Dedhar, Shoukat ;

Supuran, Claudiu T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (14) :6328-6338

[10] Synthesis of N′-phenyl-N-hydroxyureas and investigation of their inhibitory activities on human carbonic anhydrases [J].

Bozdag, Murat ;

Carta, Fabrizio ;

Angeli, Andrea ;

Osman, Sameh M. ;

Alasmary, Fatmah A. S. ;

AlOthman, Zeid ;

Supuran, Claudiu T. .

BIOORGANIC CHEMISTRY, 2018, 78 :1-6

← 1 2 3 4 5 6 7 8 9 →