Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII

被引：14

作者：

Rami, Marouan ^{[1
]}

Maresca, Alfonso ^{[2
]}

Smaine, Fatma-Zhora ^{[1
,3
]}

Montero, Jean-Louis ^{[1
]}

Scozzafava, Andrea ^{[2
]}

Winum, Jean-Yves ^{[1
]}

Supuran, Claudiu T. ^{[2
]}

机构：

[1] Ecole Natl Super Chim Montpellier, IBMM, UMR 5247, CNRS UM1 UM2, F-34296 Montpellier, France

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

[3] Univ Annaba, Fac Sci, Dept Chim, Annaba 23000, Algeria

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 10期

关键词：

Carbonic anhydrase; Isoform I; II; IX; XII; Hypoxic tumor; Boroxazolidones; Sulfonamides; Thioureas; RAY CRYSTAL-STRUCTURES; CYTOSOLIC ISOZYME-I; THERAPEUTIC APPLICATIONS; WATER-MOLECULES; HYPOXIA; INDAPAMIDE; DIURETICS; ANTITUMOR; DESIGN; TARGET;

D O I：

10.1016/j.bmcl.2011.03.055

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new series of sulfonamides was synthesized by the reaction of the boroxazolidone complex of L-lysine with isothiocyanates incorporating sulfamoyl moieties and diverse organic scaffolds. The obtained thioureas have been investigated as inhibitors of four physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII. Inhibition between the low nanomolar to the micromolar range has been observed against them, with several low nanomolar and tumor-CA selective inhibitors detected. These boron-containing compounds might be useful for the management of hypoxic tumors overexpressing hCA IX/XII by means of boron neutron capture therapy, a technique not investigated so far with inhibitors of this enzyme. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2975 / 2979

页数：5

共 52 条

[1] Human monoclonal antibodies targeting carbonic anhydrase IX for the molecular imaging of hypoxic regions in solid tumours [J].

Ahlskog, J. K. J. ;

Schliemann, C. ;

Marlind, J. ;

Qureshi, U. ;

Ammar, A. ;

Pedley, R. B. ;

Neri, D. .

BRITISH JOURNAL OF CANCER, 2009, 101 (04) :645-657

[2] In vivo targeting of tumor-associated carbonic anhydrases using acetazolamide derivatives [J].

Ahlskog, Julia K. J. ;

Dumelin, Christoph E. ;

Truessel, Sabrina ;

Marlind, Jessica ;

Neri, Dario .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (16) :4851-4856

[3]

Alterio V., 2009, DRUG DESIGN ZINC ENZ, P73

[4] Crystal structure of the catalytic domain of the tumor-associated human carbonic anhydrase IX [J].

Alterio, Vincenzo ;

Hilvo, Mika ;

Di Fiore, Anna ;

Supuran, Claudiu T. ;

Pan, Peiwen ;

Parkkila, Seppo ;

Scaloni, Andrea ;

Pastorek, Jaromir ;

Pastorekova, Silvia ;

Pedone, Carlo ;

Scozzafava, Andrea ;

Monti, Simona Maria ;

De Simone, Giuseppina .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (38) :16233-16238

[5] Expression of carbonic anhydrase IX in breast is associated with malignant tissues and is related to overexpression of c-erbB2 [J].

Bartosová, M ;

Parkkila, S ;

Pohlodek, K ;

Karttunen, TJ ;

Galbavy, S ;

Mucha, V ;

Harris, AL ;

Pastorek, J ;

Pastoreková, S .

JOURNAL OF PATHOLOGY, 2002, 197 (03) :314-321

[6]

Battke C., CANC IMMUNO IN PRESS

[7] 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

[8] Carbonic anhydrase inhibitors. Design of selective, membrane-impermeant inhibitors targeting the human tumor-associated isozyme IX [J].

Casey, JR ;

Morgan, PE ;

Vullo, D ;

Scozzafava, A ;

Mastrolorenzo, A ;

Supuran, CT .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (09) :2337-2347

[9] Carbonic anhydrase inhibitors: Water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressure-lowering agents with long-lasting effects [J].

Casini, A ;

Scozzafava, A ;

Mincione, F ;

Menabuoni, L ;

Ilies, MA ;

Supuran, CT .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (25) :4884-4892

[10] Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide [J].

Cecchi, A ;

Winum, JY ;

Innocenti, A ;

Vullo, D ;

Montero, JL ;

Scozzafava, A ;

Supuran, CT .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (23) :5775-5780

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