Acetylcholinesterase and carbonic anhydrase isoenzymes i and II inhibition profiles of taxifolin

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 31, Issue 3, 2016, Pages 441-447

  Gocer, Hulya ^a   Topal, Fevzi ^b   Topal, Meryem ^b   Küçük, Murat ^c   Teke, Dilek ^c   Gülçin, Ilhami ^c,d   Alwasel, Saleh H ^d   Supuran, Claudiu T ^e  

^a AGRI IBRAHIM CECEN UNIVERSITY   (Turkey)

^b GUMUSHANE UNIVERSITY   (Turkey)

^c ATATÜRK UNIVERSITY   (Turkey)

^d KING SAUD UNIVERSITY   (Saudi Arabia)

^e UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Acetylcholinesterase; carbonic anhydrase; enzyme inhibition; enzyme purification; taxifolin

Indexed keywords

ACETYLCHOLINESTERASE; CARBONATE DEHYDRATASE I; CARBONATE DEHYDRATASE II; DONEPEZIL; TAXIFOLIN; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE INHIBITOR; CHOLINESTERASE INHIBITOR; ISOENZYME; QUERCETIN;

ARTICLE; BINDING AFFINITY; DRUG MECHANISM; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME PURIFICATION; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; KINETIC PARAMETERS; PRIORITY JOURNAL; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; ISOLATION AND PURIFICATION; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ACETYLCHOLINESTERASE; CARBONIC ANHYDRASE INHIBITORS; CARBONIC ANHYDRASES; CHOLINESTERASE INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; HUMANS; ISOENZYMES; MOLECULAR STRUCTURE; QUERCETIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84961247798     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2015.1036051     Document Type: Article

References (110)

1. Rice-Evans CA, Miller NJ, Paganga G. Structure antioxitant activity relationships of flavanoids and phenotic acids. Free Radical Biol Med 1996;20;933-56.
2. Gulcin I. Antioxidant activity of food constituents-an overview. Arch Toxicol 2012;86:345-91.
3. Makarova K, Lastawska K, Wagner D, Wawer I. ESR study of spin trapping in Fenton media in the presence of taxifolin. J Mol Struct 2014;1067:27-36.
4. Gulcin I, Dastan A. Synthesis of dimeric phenol derivatives and determination of in vitro antioxidant and radical scavenging activities. J Enzyme Inhib Med Chem 2007;22:685-95.
5. Ak T, Gulcin I. Antioxidant and radical scavenging properties of curcumin. Chem Biol Interact 2008;174:27-37.
6. Gulcin I, Buyukokuroglu ME, Oktay M, Kufrevioglu O I. On the in vitro antioxidant properties of melatonin. J Pineal Res 2002;33: 167-71.
7. Gulcin I, Buyukokuroglu ME, Kufrevioglu O I. Metal chelating and hydrogen peroxide scavenging effects of melatonin. J Pineal Res 2003;34:278-81.
8. Gulcin I, Beydemir S, Buyukokuroglu ME. In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities. Biol Pharm Bull 2004;27:613-16.
9. Gulcin I, Beydemir S, Alici HA, et al. In vitro antioxidant properties of morphine. Pharmacol Res 2004;49:59-66.
10. Gulcin I, Berashvili D, Gepdiremen A. Antiradical and antioxidant activity of total anthocyanins from Perilla pankinensis decne. J Ethnopharmacol 2005;101:287-93.
11. Gulcin I, Elias R, Gepdiremen A, Boyer L. Antioxidant activity of lignans from fringe tree (Chionanthus virginicus L.). Eur Food Res Technol 2006;223:759-67.
12. Gocer H, Gulcin I. Caffeic acid phenethyl ester (CAPE): correlation of structure and antioxidant properties. Int J Food Sci Nutr 2011;62: 821-5.
13. Gulcin I, Beydemir S, C oban TA, Ekinci D. The inhibitory effect of dantrolene sodium and propofol on 6-phosphogluconate dehydrogenase from rat erythrocyte. Fresen Environ Bull 2008;17:1283-7.
14. Gulcin I, Elias R, Gepdiremen A, et al. Antioxidant secoiridoids from fringe tree (Chionanthus virginicus L.). Wood Sci Technol 2009;43:195-212.
15. Sisecioglu M, C ankaya M, Gulcin I, O zdemir M. The Inhibitory effect of propofol on lactoperoxidase. Protein Peptide Lett 2009;16: 46-9.
16. Gulcin I. Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology 2006;217:213-20.
17. Gulcin I. Antioxidant and antiradical activities of L-carnitine. Life Sci 2006;78:803-11.
18. Sisecioglu M, C ankaya M, Gulcin I, O zdemir M. Interactions of melatonin and serotonin to lactoperoxidase enzyme. J Enzyme Inhib Med Chem 2010;25:779-83.
19. Gulcin I. Comparison of in vitro antioxidant and antiradical activities of L-tyrosine and L-Dopa. Amino Acids 2007;32:431-8.
20. Gulcin I. Measurement of antioxidant ability of melatonin and serotonin by the DMPD and CUPRAC methods as trolox equivalent. J Enzyme Inhib Med Chem 2008;23:871-6.
21. Sisecioglu M, Gulcin I, C ankaya M, O zdemir H. The inhibitory effects of L-adrenaline on lactoperoxidase enzyme (LPO) purified from buffalo milk. Int J Food Propert 2012;15:1182-9.
22. Gulcin I. Antioxidant activity of L-adrenaline: an activity-structure insight. Chem Biol Interact 2009;179:71-80.
23. Gulcin I. Antioxidant properties of resveratrol: a structure-activity insight. Innov Food Sci Emerg 2010;11:210-18.
24. Gulcin I. Antioxidant activity of eugenol-a structure and activity relationship study. J Med Food 2011;14:975-85.
25. Kim NC, Graf TN, Sparacino CM, et al. Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). Org Biomol Chem 2003;1:1684-9.
26. Weidmann AE. Dihydroquercetin: more than just an impurity Eur J Pharmacol 2012;684:19-26.
27. Vladimirov YA, Proskurnina EV, Demin EM, et al. Dihydroquercetin (taxifolin) and other flavonoids as inhibitors of free radical formation at key stages of apoptosis. Biochemistry (Mosc) 2009;74:301-7.
28. Wang YH, Wang WY, Chang CC, et al. Taxifolin ameliorates cerebral ischemia-reperfusion injury in rats through its anti-oxidative effect and modulation of NF-kappa B activation. J Biomed Sci 2006;13:127-41.
29. Haraguchi H, Ohmi I, Fukuda A, et al. Inhibition of aldose reductase and sorbitol accumulation by astilbin and taxifolin dihydroflavonols in Engelhardtia chrysolepis. Biosci Biotechnol Biochem 1997;61: 651-4.
30. Sun X, Chen RC, Yang ZH, et al. Taxifolin prevents diabetic cardiomyopathy in vivo and in vitro by inhibition of oxidative stress and cell apoptosis. Food Chem Toxicol 2014;63:221-32.
31. Arutyunyan TV, Korystova AF, Kublik LN, et al. Effects of taxifolin on the activity of angiotensin-converting enzyme and reactive oxygen and nitrogen species in the aorta of aging rats and rats treated with the nitric oxide synthase inhibitor and dexamethasone. Age 2013;35:2089-97.
32. Middleton Jr E, Kandaswami C, Theoharides TC. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol Rev 2000;52:673-51.
33. Cermak R, Wolffram S. The potential of flavonoids to influence drug metabolism and pharmacokinetics by local gastrointestinal mechanisms. Curr Drug Metab 2006;7:729-44.
34. Egert S, Rimbach G. Which sources of flavonoids: complex diets or dietary supplements Adv Nutr 2011;2:8-14.
35. Bousová I, Hájek J, Drsata J, Skálová L. Naturally occurring flavonoids as inhibitors of purified cytosolic glutathione S-transferase. Xenobiotica 2012;42:872-9.
36. Supuran CT, Scozzafava A. Carbonic anhydrases as targets for medicinal chemistry. Bioorg Med Chem 2007;15:4336-50.
37. Zolnowska B, Slawinskia J, Pogorzelska A, et al. Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N0-(2-arylmethylthio-4-chloro-5-methyl benzenesulfonyl) guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII. Eur J Med Chem 2014;71:135-47.
38. Aksu K, Nar M, Tanc M, et al. The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties. Bioorg Med Chem 2013;21:2925-31.
39. Akincioglu A, Topal M, Gulcin I, Goksu S. Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors. Arch Pharm 2014;347:68-76.
40. Beydemir S, Gulcin I. Effect of melatonin on carbonic anhydrase from human erythrocyte in vitro and from rat erythrocyte in vivo. J Enzyme Inhib Med Chem 2004;19:193-7.
41. Coban TA, Beydemir S, Gulcin I, Ekinci D. Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo. Biol Pharm Bull 2007;30:2257-61.
42. Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168-81.
43. Akbaba Y, Akincioglu A, Gocer H, et al. Carbonic anhydrase inhibitory properties of novel sulfonamide derivatives of aminoindanes and aminotetralins. J Enzyme Inhib Med Chem 2014;29: 35-42.
44. Akbaba Y, Bastem E, Topal F, et al. Synthesis and carbonic anhydrase inhibitory effects of novel sulfamides derived from 1-aminoindanes and anilines. Arch Pharm 2014;347:950-7.
45. Cetinkaya Y, Gocer H, Goksu S, Gulcin I. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of novel benzylamine derivatives. J Enzyme Inhib Med Chem 2014;29:168-74.
46. C etinkaya Y, Gocer H, Gulcin I, Menzek A. Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives. Arch Pharm 2014;347:354-9.
47. Supuran CT, Scozzafava A. Carbonic anhydrase inhibitors and their therapeutic potential. Expert Opin Ther Pat 2000;10:575-600.
48. Mincione F, Scozzafava A, Supuran CT. In drug design of zincenzyme inhibitors: functional, structural, and disease applications. Hoboken: Wiley; 2009:139.
49. Supuran CT. Carbonic anhydrase inhibitors. Bioorg Med Chem Lett 2010;20:3467-74.
50. Guney M, Coskun A, Topal F, et al. Oxidation of cyanobenzocycloheptatrienes: synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives. Bioorg Med Chem 2014;22:3537-43.
51. Gulcin I, Beydemir S. Phenolic compounds as antioxidants: carbonic anhydrase isoenzymes inhibitors. Mini Rev Med Chem 2013;13: 408-30.
52. Nar M, Cetinkaya Y, Gulcin I, Menzek A. (3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors. J Enzyme Inhib Med Chem 2013;28:402-6.
53. De Simone G, Di Fiore A, Supuran CT. Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs Curr Pharm Des 2008;14:655-60.
54. Goksu S, Naderi A, Akbaba Y, et al. Carbonic anhydrase inhibitory properties of novel benzylsulfamides using molecular modeling and experimental studies. Bioorg Chem 2014;56:75-82.
55. Scozzafava A, Passaponti M, Supuran CT, Gulcin I, Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX, and XII). J Enzyme Inhib Med Chem 2015; DOI:10.3109/14756366.2014.956310.
56. Sethi KK, Verma SM, Tanc M, et al. Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, IX and XII with benzene sulfonamides incorporating 4-and 3-nitrophthalimide moieties. Bioorg Med Chem 2014;22:1586-95.
57. Boztas M, C etinkaya Y, Topal M, et al. Synthesis and carbonic anhydrase isoenzymes I, II, IX, and XII inhibitory effects of dimethoxy-bromophenol derivatives incorporating cyclopropane moieties. J Med Chem 2015;58:640-50.
58. Franchi M, Vullo D, Gallori E, et al. Carbonic anhydrase inhibitors: inhibition of human and murine mitochondrial isozymes V with anions. Bioorg Med Chem Lett 2003;13:2857-61.
59. Taslimi P, Gulcin I, Ozgeris B, et al. The human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibition effects of trimethoxyindane derivatives. J Enzyme Inhib Med Chem 2015; DOI:10.3109/14756366.2015.1014476.
60. Gocer H, Akncoglu A, O ztaskn N, et al. Synthesis, antioxidant and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine related compounds. Arch Pharm 2013;346:783-92.
61. Gocer H, Akncoglu A, Goksu S, et al. Carbonic anhydrase and acetylcholine esterase inhibitory effects of carbamates and sulfamoylcarbamates. J Enzyme Inhib Med Chem 2015;30: 316-20.
62. Fulton MH, Key PB. Acetylcholinesterase inhibition in estuarine fish and invertebrates as an indicator of organophosphorus insecticide exposure and effects. Environ Toxicol Chem 2001;20: 37-45.
63. Allam AR, Sridhar GR, Das UN. Elevated butrylcholinesterase and acetylcholinesterase may predict the development of type 2 diabetes mellitus and Alzheimer's disease. Med Hypotheses 2007; 69:1272-6.
64. Greenblatt HM, Dvir H, Silman I, Sussman JL. Acetylcholinesterase: a multifaceted target for structure-based drug design of anticholinesterase agents for the treatment of Alzheimer's disease. J Mol Neurosci 2003;20:369-83.
65. Costa P, Gonccalves S, Valentao P, et al. Accumulation of phenolic compounds in in vitro cultures and wild plants of Lavandula viridis L0Hér and their antioxidant and anti-cholinesterase potential. Food Chem Toxicol 2013;57:69-74.
66. Hobbiger F. The inhibition of acetylcholinesterase by organophosphorus compounds and its reversal. Proc R Soc Med 1961;54:403-5.
67. Massoulie J, Pezzementi L, Bon S, et al. Molecular and cellular biology of cholinesterases. Prog Neurobiol 1993;41:31-91.
68. Ryu HW, Curtis-Long MJ, Jung S, et al. Anticholinesterase potential of flavonols from paper mulberry (Broussonetia papyrifera) and their kinetic studies. Food Chem 2012;132:1244-50.
69. Szwajgier D. Anticholinesterase activities of selected polyphenols-a short report. Pol J Food Nutr Sci 2014;64:59-64.
70. Krikorian R, Shidler MD, Nash TA, et al. Blueberry supplementation improves memory in older adults. J Agric Food Chem 2010;58: 3996-4000.
71. Gutierres JM, Carvalho FB, Schetinger MR, et al. Anthocyanins restore behavioral and biochemical changes caused by streptozotocin-induced sporadic dementia of Alzheimer's type. Life Sci 2013; 96:7-17.
72. Pervin M, Hasnat MDA, Lee YM, et al. Antioxidant activity and acetylcholinesterase inhibition of grape skin anthocyanin (GSA). Molecules 2014;19:9403-18.
73. Zhang DB, Chen JJ, Song QY, et al. Lycodine-type alkaloids from Lycopodiastrum casuarinoides and their acetylcholinesterase inhibitory activity. Molecules 2014;19:9999-10010.
74. Aras Hisar S, Hisar O, Beydemir S, et al. Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Acta Vet Hung 2004;52: 413-22.
75. Coban TA, Beydemir S, Gulcin I, Ekinci D. The inhibitory effect of ethanol on carbonic anhydrase isoenzymes: in vivo and in vitro studies. J Enzyme Inhib Med Chem 2008;23:266-70.
76. Senturk M, Gulcin I, Beydemir S, et al. In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds. Chem Biol Drug Des 2011;77:494-9.
77. Atasaver A, O zdemir H, Gulcin I, Kufrevioglu O I. One-step purification of lactoperoxidase from bovine milk by affinity chromatography. Food Chem 2013;136:864-70.
78. Laemmli DK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970; 227:680-3.
79. Gulcin I, Kufrevioglu OI, Oktay M. Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibition effects of some chemicals on the enzyme activity. J Enzyme Inhib Med Chem 2005;20:297-302.
80. Beydemir S, Gulcin I, Hisar O, et al. Effect of melatonin on glucose-6-phospate dehydrogenase from rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. J Appl Anim Res 2005; 28:65-8.
81. Hisar O, Beydemir S, Gulcin I, et al. The effect of melatonin hormone on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo. Turk J Vet Anim Sci 2005;29:841-5.
82. Verpoorte JA, Mehta S, Edsall JT. Esterase activities of human carbonic anhydrases B and C. J Biol Chem 1967;242:4221-9.
83. Coban TA, Beydemir S, Gulcin I, et al. Sildenafil is a strong activator of mammalian carbonic anhydrase isoforms I-XIV. Bioorg Med Chem 2009;17:5791-5.
84. Gocer H, Gulcin I. Caffeic acid phenethyl ester (CAPE): a potent carbonic anhydrase isoenzymes inhibitor. Int J Acad Res 2013;5: 150-5.
85. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248-51.
86. Koksal E, Gulcin I. Purification and characterization of peroxidase from cauliflower (Brassica oleracea L.) buds. Protein Peptide Lett 2008;15:320-6.
87. Senturk M, Gulcin I, Ciftci M, Kufrevioglu OI. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharm Bull 2008;31: 2036-9.
88. Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658-66.
89. Yldrm A, Atmaca U, Keskin A, et al. N-Acylsulfonamides strongly inhibit human carbonic anhydrase isoenzymes I and II. Bioorg Med Chem 2015; DOI:10.1016/j.bmc.2014.12.054.
90. Cetinkaya Y, Gocer H, Menzek A, Gulcin I. Synthesis and antioxidant properties of (3,4-dihydroxyphenyl)(2,3,4-trihydroxyphenyl) methanone and its derivatives. Arch Pharm 2012;345: 323-34.
91. Akbaba Y, Balaydn HT, Menzek A, et al. Synthesis and biological evaluation of novel bromophenol derivatives as carbonic anhydrase inhibitors. Arch Pharm 2013;346:447-54.
92. Ozturk Sarikaya SB, Topal F, Senturk M, et al. In vitro inhibition of a-carbonic anhydrase isozymes by some phenolic compounds. Bioorg Med Chem Lett 2011;21:4259-62.
93. Ellman GL, Courtney KD, Andres V, Featherston RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol 1961;7:88-95.
94. Topal M, Gulcin I. Rosmarinic acid: a potent carbonic anhydrase isoenzymes inhibitor. Turk J Chem 2014;38:894-902.
95. Innocenti A, Gulcin I, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors. Antioxidant polyphenol natural products effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett 2010;20:5050-3.
96. Innocenti A, Ozturk Sarkaya SB, Gulcin I, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem 2010;18:2159-64.
97. 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;18:1583-7.
98. Ozturk Sarikaya SB, Gulcin I, Supuran CT. Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids. Chem Biol Drug Des 2010;75:515-20.
99. Khoddami A, Wilkes MA, Roberts TH. Techniques for analysis of plant phenolic compounds. Molecules 2013;18:2328-75.
100. Nair SK, Ludwig PA, Christianson DW. Phenol as a carbonic anhydrase inhibitor. J Am Chem Soc 1994;116:3659-60.
101. Innocenti A, Vullo D, Scozzafava A, Supuran CT. Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem 2008;16:7424-8.
102. Davis RA, Innocenti A, Poulsen SA, Supuran CT. Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library. Bioorg Med Chem 2010;18:14-18.
103. Hisar O, Beydemir S, Gulcin I, et al. Effect of low molecular weight plasma inhibitors of rainbow trout (Oncorhyncytes mykiss) on human erythrocytes carbonic anhydrase-II isozyme activity in vitro and rat erythrocytes in vivo. J Enzyme Inhib Med Chem 2005;20:35-9.
104. Akbaba Y, Turkes C, Polat L, et al. Synthesis and paroxonase activities of novel bromophenols. J Enzyme Inhib Med Chem 2013; 28:1073-9.
105. Akincioglu A, Akbaba Y, Gocer H, et al. Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors. Bioorg Med Chem 2013;21:1379-85.
106. Ogilvie JM, Ohlemiller KK, Shah GN, et al. Carbonic anhydrase XIV deficiency produces a functional defect in the retinal light response. Proc Natl Acad Sci USA 2007;104:8514-19.
107. Avvaru BS, Busby SA, Chalmers MJ, et al. Apo-human carbonic anhydrase II revisited: implications of the loss of a metal in protein structure, stability, and solvent network. Biochemistry 2009;48: 7365-72.
108. Balaydin HT, Gulcin I, Menzek A, et al. Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product. J Enzyme Inhib Med Chem 2010;25:685-95.
109. Arabaci B, Gulcin I, Alwasel S. Capsaicin: a potent inhibitor of carbonic anhydrase isoenzymes. Molecules 2014;19:10103-14.
110. Scozzafava A, Kaln P, Supuran CT, et al. The impact of hydroquinone on acetylcholine esterase and certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII). J Enzyme Inhib Med Chem 2015; DOI: 10.3109/14756366.2014.999236.