Carbonic Anhydrase Inhibitors. Cloning, Characterization, and Inhibition Studies of a New β-Carbonic Anhydrase from Mycobacterium tuberculosis

被引：101

作者：

Nishimori, Isao ^{[2
]}

Minakuchi, Tomoko ^{[2
]}

Vullo, Daniela ^{[1
]}

Scozzafava, Andrea ^{[1
]}

Innocenti, Alessio ^{[1
]}

Supuran, Claudiu T. ^{[1
]}

机构：

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

[2] Kochi Med Sch, Dept Gastroenterol, Nanko Ku, Kochi 7838505, Japan

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2009年 / 52卷 / 09期

关键词：

PH-DEPENDENT ACTIVITY; HELICOBACTER-PYLORI; CRYPTOCOCCUS-NEOFORMANS; SULFAMATE INHIBITORS; GENOME SEQUENCE; DNA CLONING; SULFONAMIDE; TARGET; ENZYME; DRUGS;

D O I：

10.1021/jm9003126

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The Rv3273 gene product of Mycobacterium tuberculosis, beta-carbonic anhydrase (CA, EC 4.2.1.1), mtCA 3, shows appreciable catalytic activity for CO2 hydration (k(cat) of 4.3 x 10(5) s(-1), and k(cat)/K-m of 4.0 x 10(7) M-1.s(-1)). A series of sulfonamides/sulfamates was assayed for their interaction with mtCA 3. Sulfanilyl-sulfonamides, acetazolamide, methazolamide, ethoxzolamide; dichlorophenamide, dorzolamide, brinzolamide, benzolamide, and zonisamide, showed effective, submicromolar inhibition (K(I)s of 104-611 nM), the best inhibitor being 2-amino-pyrimidin-4-yl-sulfanilamide (K-I of 91 nM).

引用

页码：3116 / 3120

页数：5

共 32 条

[1] Carbonic anhydrase inhibitors: X-ray and molecular modeling study for the interaction of a fluorescent antitumor sulfonamide with isozyme II and IX [J].

Alterio, Vincenzo ;

Vitale, Rosa Maria ;

Monti, Simona Maria ;

Pedone, Carlo ;

Scozzafava, Andrea ;

Cecchi, Alessandro ;

De Simone, Giuseppina ;

Supuran, Claudiu T. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) :8329-8335

[2] Evaluation of a nutrient starvation model of Mycobacterium tuberculosis persistence by gene and protein expression profiling [J].

Betts, JC ;

Lukey, PT ;

Robb, LC ;

McAdam, RA ;

Duncan, K .

MOLECULAR MICROBIOLOGY, 2002, 43 (03) :717-731

[3] Re-annotation of the genome sequence of Mycobacterium tuberculosis H37Rv [J].

Camus, JC ;

Pryor, MJ ;

Médigue, C ;

Cole, ST .

MICROBIOLOGY-SGM, 2002, 148 :2967-2973

[4] Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence [J].

Cole, ST ;

Brosch, R ;

Parkhill, J ;

Garnier, T ;

Churcher, C ;

Harris, D ;

Gordon, SV ;

Eiglmeier, K ;

Gas, S ;

Barry, CE ;

Tekaia, F ;

Badcock, K ;

Basham, D ;

Brown, D ;

Chillingworth, T ;

Connor, R ;

Davies, R ;

Devlin, K ;

Feltwell, T ;

Gentles, S ;

Hamlin, N ;

Holroyd, S ;

Hornby, T ;

Jagels, K ;

Krogh, A ;

McLean, J ;

Moule, S ;

Murphy, L ;

Oliver, K ;

Osborne, J ;

Quail, MA ;

Rajandream, MA ;

Rogers, J ;

Rutter, S ;

Seeger, K ;

Skelton, J ;

Squares, R ;

Squares, S ;

Sulston, JE ;

Taylor, K ;

Whitehead, S ;

Barrell, BG .

NATURE, 1998, 393 (6685) :537-+

[5] Structural mechanics of the pH-dependent activity of β-carbonic anhydrase from Mycobacterium tuberculosis [J].

Covarrubias, AS ;

Bergfors, T ;

Jones, TA ;

Högbom, M .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (08) :4993-4999

[6] Identification of a novel noncatalytic bicarbonate binding site in eubacterial β-carbonic anhydrase [J].

Cronk, JD ;

Rowlett, RS ;

Zhang, KYJ ;

Tu, CK ;

Endrizzi, JA ;

Lee, J ;

Gareiss, PC ;

Preiss, JR .

BIOCHEMISTRY, 2006, 45 (14) :4351-4361

[7] Crystal structure of E-coli β-carbonic anhydrase, an enzyme with an unusual pH-dependent activity [J].

Cronk, JD ;

Endrizzi, JA ;

Cronk, MR ;

O'Neill, JW ;

Zhang, KYJ .

PROTEIN SCIENCE, 2001, 10 (05) :911-922

[8] Doomsday postponed? Preventing and reversing epidemics of drug-resistant tuberculosis [J].

Dye, Christopher .

NATURE REVIEWS MICROBIOLOGY, 2009, 7 (01) :81-87

[9] Emerging drugs for active tuberculosis [J].

Ginsberg, Ann M. .

SEMINARS IN RESPIRATORY AND CRITICAL CARE MEDICINE, 2008, 29 (05) :552-559

[10] Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes [J].

Hilvo, Mika ;

Baranauskiene, Lina ;

Salzano, Anna Maria ;

Scaloni, Andrea ;

Matulis, Daumantas ;

Innocenti, Alessio ;

Scozzafava, Andrea ;

Monti, Simona Maria ;

Di Fiore, Anna ;

De Simone, Giuseppina ;

Lindfors, Mikaela ;

Janis, Janne ;

Valjakka, Jarkko ;

Pastorekova, Silvia ;

Pastorek, Jaromir ;

Kulomaa, Markku S. ;

Nordlund, Henri R. ;

Supuran, Claudiu T. ;

Parkkila, Seppo .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2008, 283 (41) :27799-27809

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