Sulfapyridine-like benzenesulfonamide derivatives as inhibitors of carbonic anhydrase isoenzymes I, II and VI

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 6, 2012, Pages 818-824

  Alp, Cemalettin ^a,b   Özsoy, Şeyda ^a   Alp, Nurdan Alcan ^a   Erdem, Deryanur ^a,c   Gültekin, Mehmet Serdar ^a   Küfrevioǧlu, Ömer Irfan ^a   Şentürk, Murat ^a,d   Supuran, Claudiu T ^e  

^a ATATÜRK UNIVERSITY   (Turkey)

^b ERZINCAN UNIVERSITY   (Turkey)

^c AKSARAY UNIVERSITY   (Turkey)

^d AGRI IBRAHIM CECEN UNIVERSITY   (Turkey)

^e UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Benzenesulfonamides; Carbonic anhydrase; Inhibition

Indexed keywords

4 AMINO N (PYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 METHYLBENZENESULFONAMIDE; ACETAZOLAMIDE; AROMATIC AMINE; BENZENESULFONAMIDE DERIVATIVE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE INHIBITOR; CARBONATE DEHYDRATASE VI; SULFAPYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; PRIORITY JOURNAL;

BENZENESULFONATES; CARBONIC ANHYDRASE I; CARBONIC ANHYDRASE II; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; ELECTROPHORESIS, POLYACRYLAMIDE GEL; ENZYME ASSAYS; ERYTHROCYTES; HUMANS; KINETICS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; SULFAPYRIDINE; SULFONAMIDES;

EID: 84866717865     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.617745     Document Type: Article

References (39)

1. Ozensoy O, Arslan O, Sinan SO. A new method for purification of carbonic anhydrase isozymes by affinity chromatography. Biochemistry Mosc 2004;69:216-219.
2. Supuran CT. Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-181.
3. 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.
4. Supuran CT, Scozzafava A, Conway J. Carbonic Anhydrase-Its Inhibitors and Activators. CRC Press: Boca Raton, New York, London, 2004. pp. 1-363.
5. Winum JY, Rami M, Scozzafava A, Montero JL, Supuran C. Carbonic anhydrase IX: A new druggable target for the design of antitumor agents. Med Res Rev 2008;28:445-463.
6. Güzel 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, Sentürk M, Ekinci D, Balaydin HT, Göksu S, Küfrevioglu ÖI 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. Kivelä J, Parkkila S, Waheed A, Parkkila AK, Sly WS, Rajaniemi H. Secretory carbonic anhydrase isoenzyme (CA VI) in human serum. Clin Chem 1997;43:2318-2322.
9. Sentürk M, Ekinci D, Göksu S, Supuran CT. Effects of dopaminergic compounds on carbonic anhydrase isozymes I, II, and VI. J Enzyme Inhib Med Chem 2011. (doi: 10.3109/14756366.2011.591290).
10. Ekinci D, Cavdar H, Talaz O, Sentürk 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, Sentürk M, Erdem D, Küfrevioglu 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, Gültekin MS, Sentürk M, Sahin E, Küfrevioglu 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, Sentürk M, Ekinci D, Erdogan O, Ciltas A, Kocaman EM. δmethrin 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. Erdogan O, Ceyhun SB, Ekinci D, Aksakal E. Impact of δmethrin exposure on mRNA expression levels of metallothionein A, B and cytochrome P450 1A in rainbow trout muscles. Gene 2011;484:13-17.
16. Ekinci D, Sentürk M, Beydemir S, Küfrevioglu OI, Supuran CT. An alternative purification method for human serum paraoxonase 1 and its interactions with sulfonamides. Chem Biol Drug Des 2010;76:552-558.
17. Aksakal E, Ceyhun SB, Erdogan O, Ekinci D. Acute and long-term genotoxicity of δmethrin to insulin-like growth factors and growth hormone in rainbow trout. Comp Biochem Physiol C Toxicol Pharmacol 2010;152:451-455.
18. Ceyhun SB, Aksakal E, Ekinci D, Erdogan O, Beydemir S. Influence of cobalt and zinc exposure on mRNA expression profiles of metallothionein and cytocrome P450 in rainbow trout. Biol Trace Elem Res. Doi: 10.1007/s12011-011- 9068-z.
19. Cakmak R, Durdagi S, Ekinci D, Sentürk M, Topal G. Design, synthesis and biological evaluation of novel nitroaromatic compounds as potent glutathione reductase inhibitors. Bioorg Med Chem Lett 2011;21:5398-5402.
20. Aksakal E, Ekinci D, Erdogan O, Beydemir S, Alim Z, Ceyhun SB. Increasing stocking density causes inhibition of metabolicantioxidant enzymes and elevates mRNA levels of heat shock protein 70 in rainbow trout. Livest Sci 2011. Doi:10.1016/j. livsci.2011.07.006.
21. Siktar E, Ekinci D, Siktar E, Beydemir S, Gulcin I, Gunay M. Protective role of L-carnitine supplementation against exhaustive exercise-induced oxidative stress in rats. Eur J Pharmacol 2011. Doi: 10.1016/j.ejphar.2011.07. 032.
22. Casini A, Scozzafava A, Mincione F, Menabuoni L, Ilies MA, Supuran CT. Carbonic anhydrase inhibitors: Water-soluble 4-sulfamoylphenylthioureas as topical intraocular pressurelowering agents with long-lasting effects. J Med Chem 2000;43:4884-4892.
23. 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-isothiocyanato-benzolamide. Bioorg Med Chem Lett 2004;14:5775-5780.
24. 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.
25. Balaydin HT, Durdagi S, Ekinci D, Senturk M, Goksu S, Menzek A. Inhibition of human carbonic anhydrase isozymes I, II and VI with a series of bisphenol, metoxy and bromophenol compounds. J Enzym Inhib Med Ch 2011. Doi:10.3109/14756366.2011.596836.
26. Senturk M, Kufrevioglu OI. In vitro effects of some nucleoside analogue drugs on enzyme activities of carbonic anhydrase isozymes I and II from human erythrocytes. Hacettepe J Biol Chem 2009;37:289-294.
27. Park KK, Lee JJ, Ryu J. Photo-Fries rearrangement of N-arylsulfonamides to aminoaryl sulfone derivatives. Tetrahedron 2003;59:7651-7659.
28. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221-4229.
29. Lineweaver H, Burk D. The determination of enzyme dissocation constants. J Am Chem Soc 1934;56:658-666.
30. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of proteindye binding. Anal Biochem 1976;72:248-254.
31. Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680-685.
32. 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.
33. 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.
34. Sentürk M, Gülçin I, Dastan A, Küfrevioglu 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.
35. Balaydin HT, Soyut H, Ekinci D, Goksu S, Beydemir S, Menzek A, Sahin E. Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products. J Enzym Inhib Med Ch 2011. Doi: 10.3109/14756366. 2011.574131.
36. Sly WS, Hu PY. Human carbonic anhydrases and carbonic anhydrase deficiencies. Annu Rev Biochem 1995;64:375-401.
37. 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.
38. Ceyhun SB, Sentürk M, Yerlikaya E, Erdogan O, Küfrevioglu 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.
39. Nair SK, Ludwig PA, Christianson DW. Two-site binding of phenol in the active site of human carbonic anhydrase II: Structural implications for substrate association. J Am Chem Soc 1994;116:3659-3660.