Secondary/tertiary benzenesulfonamides with inhibitory action against the cytosolic human carbonic anhydrase isoforms i and II

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 28, Issue 2, 2013, Pages 294-298

  Alp, Cemalettin ^a,b   Maresca, Alfonso ^c   Alp, Nurdan Alcan ^a   Gültekin, Mehmet Serdar ^a   Ekinci, Deniz ^d   Scozzafava, Andrea ^c   Supuran, Claudiu T ^c  

^a ATATÜRK UNIVERSITY   (Turkey)

^b ERZINCAN UNIVERSITY   (Turkey)

^c UNIVERSITY OF FLORENCE   (Italy)

^d ONDOKUZ MAYIS UNIVERSITY   (Turkey)

Author keywords

Benzenesulfonamide; Carbonic anhydrase; Inhibitor; Tosyl

Indexed keywords

CARBON DIOXIDE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; ISOPROTEIN; SULFONAMIDE;

ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; HUMAN; ISOLATION AND PURIFICATION; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBON DIOXIDE; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; MOLECULAR STRUCTURE; PROTEIN ISOFORMS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 84879037030     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2012.658788     Document Type: Article

References (32)

1. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008; 7: 168-181.
2. Hilvo M, Baranauskiene L, Salzano AM, Scaloni A, Matulis D, Innocenti A et al. Biochemical characterization of CA IX, one of the most active carbonic anhydrase isozymes. J Biol Chem 2008; 283: 27799-27809.
3. Alp C, Ozsoy S, Alp NA, Erdem D, Gultekin MS, Kufrevioglu OI et al. Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI. J Enzyme Inhib Med Chem 2011; doi: 10.3109/14756366.2011.617 745.
4. Fabrizi F, Mincione F, Somma T, Scozzafava G, Galassi F, Masini E et al. A new approach to antiglaucoma drugs: carbonic anhydrase inhibitors with or without NO donating moieties. Mechanism of action and preliminary pharmacology. J Enzyme Inhib Med Chem 2012; 27: 138-147.
5. Maresca A, Supuran CT. R-/(S)-10-camphorsulfonyl-substituted aromatic/heterocyclic sulfonamides selectively inhibit mitochondrial over cytosolic carbonic anhydrases. Bioorg Med Chem Lett 2011; 21: 1334-1337.
6. Guzel O, Innocenti A, Scozzafava A, Salman A, Parkkila S, Hilvo M et al. Carbonic anhydrase inhibitors: synthesis and inhibition studies against mammalian isoforms I-XV with a series of 2-(hydrazinocarbonyl)-3-substituted-phenyl-1H-indole-5- sulfonamides. Bioorg Med Chem 2008; 16: 9113-9120.
7. Durdagi S, Senturk M, Ekinci D, Balaydin HT, Goksu S, Kufrevioglu OI et al. Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site. Bioorg Med Chem 2011; 19: 1381-1389.
8. Neri D, Supuran CT. Interfering with pH regulation in tumours as a therapeutic strategy. Nat Rev Drug Discov 2011; 10: 767-777.
9. Senturk M, Ekinci D, Goksu S, Supuran CT. Effects of dopaminergic compounds on carbonic anhydrase isozymes I, II, and VI. J Enzym Inhib Med Chem 2012; doi: 10.3109/14756366.20 11.591290.
10. Ekinci D, Cavdar H, Talaz O, Senturk M, Supuran CT. NO-releasing esters show carbonic anhydrase inhibitory action against human isoforms I and II. Bioorg Med Chem 2010; 18: 3559-3563.
11. Ekinci D, Ceyhun SB, Senturk M, Erdem D, Kufrevioglu OI, Supuran CT. Characterization and anions inhibition studies of an a-carbonic anhydrase from the teleost fish Dicentrarchus labrax. Bioorg Med Chem 2011; 19: 744-748.
12. Alp C, Ekinci D, Gultekin MS, Senturk M, Sahin E, Kufrevioglu OI. A novel and one-pot synthesis of new 1-tosyl pyrrol-2- one derivatives and analysis of carbonic anhydrase inhibitory potencies. Bioorg Med Chem 2010; 18: 4468-4474.
13. Ekinci D, Ceyhun SB, Aksakal E, Erdogan O. IGF and GH mRNA levels are suppressed upon exposure to micromolar concentrations of cobalt and zinc in rainbow trout white muscle. Comp Biochem Physiol C Toxicol Pharmacol 2011; 153: 336-341.
14. Ceyhun SB, Senturk M, Ekinci D, Erdogan O, Ciltas A, Kocaman EM. Deltamethrin attenuates antioxidant defense system and induces the expression of heat shock protein 70 in rainbow trout. Comp Biochem Physiol C Toxicol Pharmacol 2010; 152: 215-223.
15. Casini A, Scozzafava A, Mincione F, Menabuoni L, Ilies MA, Supuran CT. Carbonic anhydrase inhibitors (Part 99): Water soluble 4-sulfamoylphenylthioureas as topical intraocular pressure lowering agents with long lasting effects. J Med Chem 2000; 43: 4884-4892.
16. Cecchi A, Winum JY, Innocenti A, Vullo D, Montero JL, Scozzafava A et al. Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanatobenzolamide. Bioorg Med Chem Lett 2004; 14: 5775-5780.
17. Innocenti A, Casini A, Alcaro MC, Papini AM, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: the first on-resin screening of a 4-sulfamoylphenylthiourea library. J Med Chem 2004; 47: 5224-5229.
18. Bayram E, Senturk M, Kufrevioglu OI, Supuran CT. In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg Med Chem 2008; 16: 9101-9105.
19. Khalifah RG. The carbon dioxide hydration activity of carbonic anhydrase. I. Stop-flow kinetic studies on the native human isoenzymes B and C. J Biol Chem 1971; 246: 2561-2573.
20. Park KK, Lee JJ, Ryu J. Photo-Fries rearrangement of N-arylsulfonamides to aminoaryl sulfone derivatives. Tetrahedron 2003; 59: 7651-7676.
21. Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 1973; 22: 3099-3108.
22. Nuti E, Orlandini E, Nencetti S, Rossello A, Innocenti A, Scozzafava A et al. Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I and II with sulfonylated hydroxamates. Bioorg Med Chem 2007; 15: 2298-2311.
23. Briganti F, Pierattelli R, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Part 37. Novel classes of isozymes I and II inhibitors and their mechanism of action. Kinetic and spectroscopic investigations on the native and cobalt-substituted enzymes. Eur J Med Chem 1996; 31: 1001-1010.
24. Senturk M, Gulcin I, Dastan A, Kufrevioglu OI, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols. Bioorg Med Chem 2009; 17: 3207-3211.
25. Senturk M, Gulcin I, Beydemir S, Kufrevioglu OI, Supuran CT. In vitro inhibition of human carbonic anhydrase i and ii isozymes with natural phenolic compounds. Chem Biol Drug Des 2011; 77: 494-499.
26. Cavdar H, Ekinci D, Talaz O, Saracoglu N, Senturk M, Supuran CT. α-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters. J Enzyme Inhib Med Chem 2012; 27: 148-154.
27. Pastorekova S, Parkkila S, Pastorek J, Supuran CT. Carbonic anhydrases: current state of the art, therapeutic applications and future prospects. J Enzyme Inhib Med Chem 2004; 19: 199-229.
28. Ceyhun SB, Senturk M, Yerlikaya E, Erdogan O, Kufrevioglu OI, Ekinci D. Purification and characterization of carbonic anhydrase from the teleost fish Dicentrarchus labrax (European seabass) liver and toxicological effects of metals on enzyme activity. Environ Toxicol Pharmacol 2011; 32: 69-74.
29. Maresca A, Temperini C, Vu H, Pham NB, Poulsen SA, Scozzafava A et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors. J Am Chem Soc 2009; 131: 3057-3062.
30. Maresca A, Supuran CT. Coumarins incorporating hydroxy- and chloro-moieties selectively inhibit the transmembrane, tumorassociated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II. Bioorg Med Chem Lett 2010; 20: 4511-4514.
31. Maresca A, Scozzafava A, Supuran CT. 7, 8-disubstitutedbut not 6, 7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/ subnanomolar range. Bioorg Med Chem Lett 2010; 20: 7255-7258.
32. Carta F, Maresca A, Scozzafava A, Supuran CT. 5- and 6-Membered (thio)lactones are prodrug type carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2012; 22: 267-270.