α-Carbonic anhydrases are sulfatases with cyclic diol monosulfate esters

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 1, 2012, Pages 148-154

  Çavdar, Hseyin ^a   Ekinci, Deniz ^b   Talaz, Oktay ^c   Saraçoǧlu, Nurullah ^d   Šentürk, Murat ^e   Supuran, Claudiu T ^f  

^a DUMLUPINAR UNIVERSITY   (Turkey)

^b ONDOKUZ MAYIS UNIVERSITY   (Turkey)

^c KARAMANOGLU MEHMETBEY UNIVERSITY   (Turkey)

^d ATATÜRK UNIVERSITY   (Turkey)

^e AGRI IBRAHIM CECEN UNIVERSITY   (Turkey)

^f UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Antiglaucoma; Carbonic anhydrase; Cyclic diols; Inhibition

Indexed keywords

ALCOHOL; ALPHA CARBONIC ANHYDRASE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; CARBONATE DEHYDRATASE IV; CARBONATE DEHYDRATASE VI; CYCLIC DIOL MONOSULFATE ESTER; SULFATASE; SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME MECHANISM; ENZYME SUBSTRATE; ENZYME SYNTHESIS; PRIORITY JOURNAL;

ALCOHOLS; BIOCATALYSIS; CARBONIC ANHYDRASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; ESTERS; HUMANS; HYDROLYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84855366173     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.629198     Document Type: Article

References (52)

1. Innocenti A, Scozzafava A, Parkkila S, Puccetti L, De Simone G, Supuran CT. Investigations of the esterase, phosphatase, and sulfatase activities of the cytosolic mammalian carbonic anhydrase isoforms I, II, and XIII with 4-nitrophenyl esters as substrates. Bioorg Med Chem Lett 2008;18:2267-2271. (Pubitemid 351442910)
2. Innocenti A, Supuran CT. Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of α-but not of ß-, γ-and ζ-carbonic anhydrases. Bioorg Med Chem Lett 2010;20:6208-6212.
3. Kaiser ET, Lo KW. The carbonic anhydrase catalyzed hydrolysis of 2-hydroxy-5-nitro-α-toluenesuIfonic acid sultone. J Am Chem Soc 1969;91:4912-4918.
4. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-181. (Pubitemid 351194064)
5. Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336-4350. (Pubitemid 46777288)
6. Sly WS, Hu PY. Human carbonic anhydrases and carbonic anhydrase deficiencies. Annu Rev Biochem 1995;64:375-401.
7. Parkkila S, Parkkila AK. Carbonic anhydrase in the alimentary tract. Roles of the different isozymes and salivary factors in the maintenance of optimal conditions in the gastrointestinal canal. Scand J Gastroenterol 1996;31:305-317. (Pubitemid 26117752)
8. 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. (Pubitemid 39004275)
9. 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.
10. Sentürk M, Gülçin I, Beydemir S, Küfrevioglu 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.
11. 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.
12. 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.
13. Innocenti A, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV). Bioorg Med Chem Lett 2008;18:1583-1587. (Pubitemid 351320621)
14. 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.
15. D'Ambrosio K, Vitale RM, Dogné JM, Masereel B, Innocenti A, Scozzafava A et al. Carbonic anhydrase inhibitors: bioreductive nitrocontaining sulfonamides with selectivity for targeting the tumor associated isoforms IX and XII. J Med Chem 2008;51:3230-3237. (Pubitemid 351821882)
16. Ozturk Sarikaya SB, Topal F, Senturk M, Gulcin I, Supuran CT. In vitro inhibition of α-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259-4262.
17. 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.
18. Supuran CT, Scozzafava A, Casini A. Carbonic anhydrase inhibitors. Med Res Rev 2003;23:146-189. (Pubitemid 36241096)
19. Ceyhun SB, Sentürk 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.
20. Ceyhun SB, Senturk M, Yerlikaya E, Erdogan O, Kufrevioglu OI, Ekinci D. In vitro and in vivo effects 321 of some pesticides on carbonic anhydrase enzyme from rainbow trout (Oncorhynchus 322 mykiss) gills. Pestic Biochem Physiol 2010;97:177-181.
21. Winchester BG. Iminosugars: from botanical curiosities to licensed drugs. Tetrahedron 2009;20:645-651.
22. Scott LJ, Spencer CM. Miglitol: a review of its therapeutic potential in type 2 diabetes mellitus. Drugs 2000;59:521-549. (Pubitemid 30213863)
23. Yu Z, Sawkar AR, Whalen LJ, Wong CH, Kelly JW. Isofagomineand 2,5-anhydro-2,5-imino-D-glucitol-based glucocerebrosidase pharmacological chaperones for Gaucher disease intervention. J Med Chem 2007;50:94-100. (Pubitemid 46105502)
24. Saracoglu N, Talaz O, Azizoglu A, Watson WH, Balci M. Synthesis and structure of cyclopropano-annelated homosesquinorbornene derivatives containing pyramidalized double bonds: evidence for the sterical effect of a cyclopropyl group on the degree of C=C double-bond pyramidalization. J Org Chem 2005;70:5403-5408. (Pubitemid 40980748)
25. 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.
26. Hughes AB, Rudge AJ. Deoxynojirimycin: synthesis and biological activity. Nat Prod Rep 1994;11:135-162.
27. Heightman TD, Vasella AT. Recent insights into inhibition, structure, and mechanism of configuration-retaining glycosidases. Angew Chem Int Ed 1999;38:750-770.
28. Kornprobst JM, Sallenave C, Barnathan G. Sulfated compounds from marine organisms. Comp Biochem Physiol B, Biochem Mol Biol 1998;119:1-51. (Pubitemid 28101939)
29. Cavdar H, Saracoglu N. Synthesis of new beta-hydroxy nitrate esters as potential glycomimetics or vasodilators. Eur J Org Chem 2008;4615-4621.
30. Senturk M, Ekinci D, Goksu 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.
31. 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.
32. 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.
33. Erdogan O, Ceyhun SB, Ekinci D, Aksakal E. Impact of deltamethrin exposure on mRNA expression levels of metallothionein A, B and cytochrome P450 1A in rainbow trout muscles. Gene 2011;484:13-17.
34. 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.
35. Aksakal E, Ceyhun SB, Erdogan O, Ekinci D. Acute and longterm genotoxicity of deltamethrin to insulin-like growth factors and growth hormone in rainbow trout. Comp Biochem Physiol C Toxicol Pharmacol 2010;152:451-455.
36. 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 2011;doi:10.1007/s12011- 011-9068-z.
37. 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.
38. 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;141:69-75.
39. Siktar E, Ekinci D, Siktar E, Beydemir S, Gülçin I, Günay M. Protective role of l-carnitine supplementation against exhaustive exercise induced oxidative stress in rats. Eur J Pharmacol 2011;668:407-413.
40. 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 Enzyme Inhib Med Chem 2011;doi:10.3109/14756366.2011.596836.
41. 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.
42. Senturk M, Ekinci D, Alici HA, Beydemir S. Paraoxonase-1, an organophosphate detoxifier and cardioprotective enzyme, is inhibited by anesthetics: an in vitro and in vivo insight. Pestic Biochem Physiol 2011;doi:10.1016/j.pestbp.2011.09.007.
43. Ekinci D, Beydemir S. Risk assessment of pesticides and fungicides for acid-base regulation and salt transport in rainbow trout tissues. Pestic Biochem Physiol 2010;97:66-70.
44. Ekinci D, Beydemir S. Purification of PON1 from human serum and assessment of enzyme kinetics against metal toxicity. Biol Trace Elem Res 2010;135:112-120.
45. Wistrand PJ, Carter ND, Conroy CW, Mahieu I. Carbonic anhydrase IV activity is localized on the exterior surface of human erythrocytes. Acta Physiol Scand 1999;165:211-218. (Pubitemid 29090270)
46. Whitney PL, Briggle TV. Membrane-associated carbonic anhydrase purified from bovine lung. J Biol Chem 1982;257:12056-12059. (Pubitemid 13168897)
47. 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. (Pubitemid 28022967)
48. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242: 4221-4229.
49. Lineweaver H, Burk D. The determination of enzyme dissocation constants. J Am Chem Soc 1934;56:658-666.
50. 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.
51. Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970;227:680-685.
52. Cavdar H, Saracoglu N. Ring opening of epoxides with NaHSO4: isolation of beta-hydroxy sulfate esters and an effective synthesis for trans-diols. Tetrahedron 2009;65:985-989.