Inhibitory Properties of Aniline, Aminophenol Compounds and their N-acetylated Derivatives on Carbonic Anhydrase

Abstract

Carbonic anhydrases (CAs) are a group of metalloenzymes responsible for speeding up the conversion of carbon dioxide and water to a bicarbonate ion and a proton. CAs is divided into seven well-defined classes, namely, alpha, beta, gamma, delta, zeta, eta and theta. The alpha class of CAs is found in animal systems and is involved in various physiological and pathological processes. In some cases CA inhibition is required to treat certain disorders. Over the years metal complexing anions and sulfonamide compounds have been used extensively for this purpose. This paper investigated the potential inhibitory properties of aminophenol (AP) compounds and their acetylated derivatives against human cytosolic carbonic anhydrase (hCA) isozymes I and II. 

Keywords

• Carbonic anhydrase,aminophenol,inhibitory

References

1. ALP, C., EKINCI, D., GULTEKIN, M. S., SENTURK, M., SAHIN, E., KUFREVIOGLU, O. I. (2010), A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies. Bioorg. Med. Chem., 18:4468-4474.
2. ARMITAGE, M., BRET, G., CHOUDARY, B. M., KINGSWOOD, M., LOFT, M., MOORE, S., SMITH, S., URQUHART, M. W. (2012), Identification and development of an efficient route to SB-649915. J. Org. Process Res. Dev., 16 (10):1626-1634.
3. BARBER, M. (1944), Antibacterial action of 2-aminophenol. Br. Med. J., 2 (4379):754-755.
4. BENDARY, E., FRANCIS, R. R., ALI, H. M. G, SARWAT, M. I., EL HADY, S. (2013), Antioxidant and structure-activity relationships (SARs) of some phenolic and anilines compounds. Annals Agric. Sci., 58 (2):173-181.
5. CAPASSO C., SUPURAN, C. T. (2016), An overview of the carbonic anhydrases from two pathogens of the oral cavity: Streptococcus mutans and Porphyromonas gingivalis. Curr. Top. Med. Chem., 16:2359-2368.
6. CAPASSO C., SUPURAN, C. T. (2015), An overview of the selectivity and efficiency of the bacterial carbonic anhydrase inhibitors. Curr. Med. Chem., 2:2130-2139.
7. CAPASSO C., SUPURAN, C. T. (2015), Bacterial, fungal and protozoan carbonic anhydrases as drug targets. Expert Opin. Ther. Targets, 19:1689-1704. DE SIMONE G., DI FIORE A., CAPASSO C., SUPURAN C. T. (2015), The zinc coordination pattern in the eta-carbonic anhydrase from Plasmodium falciparum is different from all other carbonic anhydrase genetic families. Bioorgan. Med. Chem. Lett., 25:1385-1389.
8. DEL PRETE S., VULLO D., FISHER G. M., ANDREWS K. T., POULSEN S. A. CAPASSO C., SUPURAN C. T. (2014), Discovery of a new family of carbonic anhydrase in the malaria pathogen Plasmodium falciparum – The η-carbonic anhydrases. Bioorgan. Med. Chem. Lett., 24:4389-4396.

9. DEMIRDAG, R., COMAKLI, V., SENTURK, M., EKİNCİ, D., KUFREVIOGLU, O. I. (2013), Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity. Bioorg. Med. Chem., 21:1522-1525.
10. GIURG M., GOLAP A., SUCHODOLSKI J., KALETA R., KRASOWSKA A., PIASECKI E., PIETKA-OTTLIK M. (2017), Reactions of bis((2-chlorocarbonyl)phenyl) diselenide with phenols, aminophenols and other amimes towards diphenyl diselenides with antimicrobials and antiviral properties. Molecules, 22(6):974-996.
11. HASSAN M. I., SHAJEE B., WAHEED A., AHMAD F., SLY W.S. (2013), Structure, function and applications of carbonic anhydrase isozymes. Bioorg. Med. Chem., 21:1570-1582.
12. INNOCENTI, A. I., HILVO, M., SCOZZAFAVA, A., PARKKILA, S., SUPURAN, C. T. (2008), Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg. Med. Chem. Lett., 18:3593-3596.
13. INNOCENTI, A. I., VULLO, D., SCOZZAFAVA, A., SUPURAN, C. T. (2008), Carbonic anhydrase inhibitors: Interactions of phenols with the 12 catalytically active mammalian isoforms (CA 1-XIV). Bioorg. Med. Chem. Lett., 18:1583-1587.
14. JADHAV, B. D., PARDESHI, S. K. (2016), A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent oranobismuth compounds with amines and N-heteroarenes. RSC Advances, 6 (18):14531-14537.
15. JONCOUR, R., DUGUET, N., METAY, E., FERREIRA, A. LEMAIRE, M. (2014), Amidation of phenol derivatives: a direct synthesis of paracetamol (acetaminophen) from hydroquinone. Green Chemistry, 16 (6):2997-3002.
16. KRUNGKRAI J. (2005), Carbonic anhydrase inhibitors. Inhibition of Plasmodium falciparum carbonic anhydrase with aromatic sulfonamides: towards antimalarials with novel mechanism of action?, Biorg. Med. Chem.,13(2):483-489.
17. LINEWEAVER, H., BURK, D. (1934), The determination of enzyme dissociation constants. J. Am. Chem. Soc., 57:685.
18. MANN, T., KEILIN, D. (1940), Sulphanilamide as a specific inhibitor of carbonic anhydrase. Nature, 146:164-165.
19. MINCIONE F., SCOZZAFAVA A., SUPURAN C. T. (2007), The development of topically acting carbonic anhydrase inhibitors as anti-glaucoma agents. Curr. Top. Med. Chem.,7:849-854.
20. NAIR S. K., LUDWIG P. A., CHRISTIANSON D: W. (1994), Two-site binding of phenol in the active site of human Carbonic Anhydrase II: Structural ımplications for substrate association. J. Am. Chem. Soc., 116:3659-3660.
21. OZENSOY GULER O., CAPASSO C., SUPURAN C. T. (2016), A magnificent enzyme superfamily: Carbonic anhydrases, their purification and characterization. J. Enzym. Inhib. Med. Chem., 31:689-694.
22. PICARD F. (2000), Topiramate reduces energy and fat gains in lean (Fa/?) and obese (fa/fa) Zucker rats. Obesity Res., 8:656-663.
23. PISANESCHI, F., SEJBERG, J. J. P., BLAIN, C., NG, W. H., ABOAGYE, E. O., SPIVEY, A. C. (2011), 2-substituted-2,3-dihydro-1H-quinolin-4-ones via acid catalyzed tandem Rupe rearrangement-Donnelly-Farrell ring closure of 2-(3’-hydroxypropynyl)anilines. Synlett, , 2:241-244.
24. RIIHONEN R., SUPURAN C. T., PARKKILA S., PASTOREKOVA S., VÄÄNÄNEN H. K., LAITALA-LEINONEN T. (2007), Membrane-bound carbonic anhydrases in osteoclasts. Bone., 40:1021-1031.
25. SARIKAYA, S. B. O., TOPAL, F., SENTÜURK, M. GULCIN, I., SUPURAN, C. T. (2011), In vitro inhibition of α-carbonic anhydrase isoenzymes by some phenolic compounds. Bioorg. Med. Chem. Lett., 21:4259-4262.
26. SCOZZAFAVA A., MASTROLORENZO A., SUPURAN C. T. (2006), Carbonic anhydrase inhibitors and activators and their use in therapy. Expert Opin. Ther. Pat., 16:1627-1664.
27. SHADYRO O. I., KSENDZOVA G. A., POLOZOV G. I., SOROKIN V. L., BOREKO E. I., SAVINOVA O. V., DUBOVIK B. V., BIZUNOK N. A. (2008), Synthesis and study of antiviral and anit-radical properties of aminophenol derivatives. Bioorg. Med. Chem. Lett., 18(7):2420-2423.
28. SIMONSSON, I., JONSSON, B. H., LINDSKOG, S. (1982), Phenol, a competitive inhibitor of CO2 hydration catalyzed by carbonic anhydrase. Biochem. Biophys. Res. Commun., 108(4):1406-1412.
29. SINGH, T., LAKHAN, R., SINGH, G. S. (2017), Chemoselecive N-benzoylation of aminophenols employing benzoylisothio cyanates, Arabian J. Chem, 10:2778-2781.
30. SLY W. S., HEWETT-EMMETT D., WHYTE M. P., YU Y. S., TASHIAN R. E. (1983), Carbonic anhydrase II deficiency identified as the primary defect in the autosomal recessive syndrome of osteopetrosis with renal tubular acidosis and cerebral calcification. Proc. Natl. Acad. Sci. USA., 80 (9):2752.
31. SPLENDIANI G., CONDO S. (2006), Diuretic therapy in heart failure. J. Ital. Nefrol., 23:74-76.
32. SUGRUE M. F. (2000), Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog. Retin. Eye Res., 19:87-112.
33. SUPURAN C. T. (2008), Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat. Rev. Drug Discov., 7:168-179.
34. SUPURAN C. T. (2008), Carbonic anhydrases-an overview. Curr. Pharm. Des., 14:603-614.
35. SUPURAN C. T. (2017), Advances in structure-based drug discovery of carbonic anhydrase inhibitors. Expert Opin. Drug Discovery., 12:61-88.
36. SUPURAN C. T. (2017), Carbonic anhydrase inhibition and the management of hypotoxic tumours. Metabolites, 7:48-61.
37. SUPURAN, C. T., CAPASSO C. (2017), Carbonic anhydrase from Porphyromonas Gingivalis as a Drug Target. Pathogens., 6 (3):30-43.
38. VERPOORTE, J. A., MEHTA, S., EDSALL, J. T. (1976), Esterase Activities of Human Carbonic Anhydrases. J. Biol. Chem., 242:4221-4229.
39. VULLO D., FRANCHI AM., GALLORI E., PASTOREK J., SCOZZAFAVA A., PASTOREKOVA S., SUPURAN C. T. (2003), Carbonic anhydrase inhibitors. Inhibition of the tumor-associated isozyme XI with aromatic and heterocyclic sulfonamides. Bioorg. Med. Chem. Lett., 13:1005-1009.
40. VULLO D., INNOCENTI A., NISHIMORI I., PASTOREK J., SCOZZAFAVA A., PASTOREKOVA S., SUPURAN C. T. (2005), Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides – a new target for the design of antitumor and antiglaucoma drugs? Bioorg. Med. Chem. Lett., 15:963-969.