{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,8]],"date-time":"2026-10-08T10:44:43Z","timestamp":1791456283918,"version":"4.3.4"},"reference-count":73,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2014,7,10]],"date-time":"2014-07-10T00:00:00Z","timestamp":1404950400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Carbonic anhydrase (CA, EC 4.2.1.1) is a zinc containing metalloenzyme that catalyzes the rapid and reversible conversion of carbon dioxide (CO2) and water (H2O) into a proton (H+) and bicarbonate (HCO3\u2013) ion. On the other hand, capsaicin is the main component in hot chili peppers and is used extensively used in spices, food additives and drugs; it is responsible for their spicy flavor and pungent taste. There are sixteen known CA isoforms in humans. Human CA isoenzymes I, and II (hCA I and hCA II) are ubiquitous cytosolic isoforms. In this study, the inhibition properties of capsaicin against the slow cytosolic isoform hCA I, and the ubiquitous and dominant rapid cytosolic isozymes hCA II were studied. Both CA isozymes were inhibited by capsaicin in the micromolar range. This naturally bioactive compound has a Ki of 696.15 \u00b5M against hCA I, and of 208.37 \u00b5M against hCA II.<\/jats:p>","DOI":"10.3390\/molecules190710103","type":"journal-article","created":{"date-parts":[[2014,7,10]],"date-time":"2014-07-10T11:22:59Z","timestamp":1404991379000},"page":"10103-10114","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":145,"title":["Capsaicin: A Potent Inhibitor of Carbonic Anhydrase Isoenzymes"],"prefix":"10.3390","volume":"19","author":[{"given":"Betul","family":"Arabaci","sequence":"first","affiliation":[{"name":"Atat\u00fcrk University, Faculty of Sciences, Department of Chemistry, Erzurum 25240, Turkey"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5993-1668","authenticated-orcid":false,"given":"Ilhami","family":"Gulcin","sequence":"additional","affiliation":[{"name":"Atat\u00fcrk University, Faculty of Sciences, Department of Chemistry, Erzurum 25240, Turkey"},{"name":"Zoology Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Saleh","family":"Alwasel","sequence":"additional","affiliation":[{"name":"Zoology Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2014,7,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4336","DOI":"10.1016\/j.bmc.2007.04.020","article-title":"Carbonic anhydrases as targets for medicinal chemistry","volume":"15","author":"Supuran","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1016\/j.ejmech.2013.10.081","article-title":"Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII","volume":"71","author":"Pogorzelska","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2925","DOI":"10.1016\/j.bmc.2013.03.077","article-title":"The synthesis of sulfamide analogues of dopamine related compounds and their carbonic anhydrase inhibitory properties","volume":"21","author":"Aksu","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1002\/ardp.201300273","article-title":"Novel sulfamides and sulfonamides incorporating tetralin scaffold as carbonic anhydrase and acetylcholine esterase inhibitors","volume":"347","author":"Topal","year":"2014","journal-title":"Arch. Pharm."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"168","DOI":"10.3109\/14756366.2012.763163","article-title":"Synthesis and carbonic anhydrase isoenzymes inhibitory effects of novel benzylamine derivatives","volume":"29","year":"2014","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1038\/nrd2467","article-title":"Carbonic anhydrases: Novel therapeutic applications for inhibitors and activators","volume":"7","author":"Supuran","year":"2008","journal-title":"Nat. Rev. Drug Disc."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"35","DOI":"10.3109\/14756366.2012.750311","article-title":"Carbonic anhydrase inhibitory properties of novel sulfonamide derivatives of aminoindanes and aminotetralins","volume":"29","author":"Akbaba","year":"2014","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1248\/bpb.27.613","article-title":"In vitro and in vivo effects of dantrolene on carbonic anhydrase enzyme activities","volume":"27","author":"Beydemir","year":"2004","journal-title":"Biol. Pharm. Bull."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1080\/14756360310001656736","article-title":"Effect of melatonin on carbonic anhydrase from human erythrocyte in vitro and from rat erythrocyte in vivo","volume":"19","author":"Beydemir","year":"2004","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_10","first-page":"408","article-title":"Phenolic compounds as antioxidants: Carbonic anhydrase isoenzymes inhibitors","volume":"13","author":"Beydemir","year":"2013","journal-title":"Mini Rev. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3537","DOI":"10.1016\/j.bmc.2014.04.007","article-title":"Oxidation of cyanobenzocycloheptatrienes: Synthesis, photooxygenation reaction and carbonic anhydrase isoenzymes inhibition properties of some new benzotropone derivatives","volume":"22","author":"Guney","year":"2014","journal-title":"Bioorg. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3467","DOI":"10.1016\/j.bmcl.2010.05.009","article-title":"Carbonic anhydrase inhibitors","volume":"20","author":"Supuran","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"402","DOI":"10.3109\/14756366.2012.670807","article-title":"(3,4-Dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives as carbonic anhydrase isoenzymes inhibitors","volume":"28","author":"Nar","year":"2013","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1517\/13543776.10.5.575","article-title":"Carbonic anhydrase inhibitors and their therapeutic potential","volume":"10","author":"Supuran","year":"2000","journal-title":"Exp. Opin. Ther. Patents"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Supuran, C.T., and Winum, J.Y. (2009). Antiglaucoma Carbonic Anhydrase Inhibitors as Ophthalomologic Drugs. In Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications, Wiley.","DOI":"10.1002\/9780470508169"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"655","DOI":"10.2174\/138161208783877820","article-title":"Are carbonic anhydrase inhibitors suitable for obtaining antiobesity drugs?","volume":"14","author":"Supuran","year":"2008","journal-title":"Curr. Pharm. Des."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1586","DOI":"10.1016\/j.bmc.2014.01.031","article-title":"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","volume":"22","author":"Sethi","year":"2014","journal-title":"Bioorg. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2857","DOI":"10.1016\/S0960-894X(03)00581-X","article-title":"Carbonic anhydrase inhibitors: Inhibition of human and murine mitochondrial isozymes V with anions","volume":"13","author":"Franchi","year":"2003","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/j.jtemb.2013.01.001","article-title":"Impact of zinc, selenium and lycopene on capsaicin induced mutagenicity and oxidative damage in mice","volume":"27","author":"Banjia","year":"2013","journal-title":"J. Trace Elem. Med. Biol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1034","DOI":"10.1016\/j.nutres.2013.08.007","article-title":"Capsaicin and evodiamine ingestion does not augment energy expenditure and fat oxidation at rest or after moderately-intense exercise","volume":"33","author":"Schwarz","year":"2013","journal-title":"Nutr. Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/j.ejphar.2013.10.053","article-title":"Mechanisms and clinical uses of capsaicin","volume":"720","author":"Sharma","year":"2013","journal-title":"Eur. J. Pharmacol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"358","DOI":"10.1016\/j.jff.2014.04.001","article-title":"Enhanced oral bioavailability of capsaicin in mixed polymeric micelles: Preparation, in vitro and in vivo evaluation","volume":"8","author":"Zhu","year":"2014","journal-title":"J. Funct. Foods"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2075","DOI":"10.1021\/jf970972z","article-title":"Changes in capsaicinoids during development, maturation, and senescence of chile peppers and relation with peroxidase activity","volume":"46","author":"Yahia","year":"1998","journal-title":"J. Agric. Food Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"435","DOI":"10.1080\/10408399109527536","article-title":"Capsicum-production, technology, chemistry, and quality. Part V. Impact on physiology, pharmacology, nutrition, and metabolism; structure, pungency, pain, and desensitization sequences","volume":"29","author":"Govindarajan","year":"1991","journal-title":"Crit. Rev. Food Sci. Nutr."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1845","DOI":"10.1016\/0024-3205(95)00159-4","article-title":"Capsaicin, a double-edged sword: Toxicity, metabolism, and chemopreventive potential","volume":"56","author":"Surh","year":"1995","journal-title":"Life Sci."},{"key":"ref_26","first-page":"669","article-title":"Capsaicin, a unique anti-oxidant, anti-inflammatory, analgesic compound with antifungal activity against dermatophytes","volume":"24","author":"Chowdhury","year":"1996","journal-title":"Med. Sci. Res."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3877","DOI":"10.1016\/j.fct.2012.08.040","article-title":"Combined treatment with capsaicin and resveratrol enhances neuroprotection against glutamate-induced toxicity in mouse cerebral cortical neurons","volume":"50","author":"Lee","year":"2012","journal-title":"Food Chem. Toxicol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"997","DOI":"10.1016\/j.jff.2013.04.014","article-title":"Functional food ingredients for the management of obesity and associated co-morbidities-A review","volume":"5","author":"Baboota","year":"2013","journal-title":"J. Funct. Foods"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/0167-4889(94)90198-8","article-title":"Role of capsaicin, curcumin and dietary n-3 fatty acids in lowering the generation of reactive oxygen species in rat peritoneal macrophages","volume":"1224","author":"Joe","year":"1994","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"634","DOI":"10.1016\/j.neuint.2011.01.027","article-title":"Capsaicin prevents kainic acid-induced epileptogenesis in mice","volume":"58","author":"Lee","year":"2011","journal-title":"Neurochem. Int."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1111\/j.1440-1746.1993.tb01644.x","article-title":"The effect of chilli and its pungent ingredient capsaicin on gastrointestinal transit in the rat","volume":"8","author":"Kang","year":"1993","journal-title":"J. Gastroenterol. Hepatol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2809","DOI":"10.1158\/0008-5472.CAN-10-3756","article-title":"The two faces of capsaicin","volume":"71","author":"Bode","year":"2011","journal-title":"Cancer Res."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1016\/S0006-8993(98)00788-4","article-title":"Neonatal primary neuronal death induced by capsaicin and axotomy involves an apoptotic mechanism","volume":"807","author":"Sugimoto","year":"1998","journal-title":"Brain Res."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1016\/0006-291X(87)90479-7","article-title":"Capsaicin, a pungent principle of hot red pepper, evokes catecholamine secretion from the adrenal medulla of anesthetized rats","volume":"142","author":"Watanabe","year":"1987","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"e67786","DOI":"10.1371\/journal.pone.0067786","article-title":"Acute effects of capsaicin on energy expenditure and fat oxidation in negative energy balance","volume":"8","author":"Janssens","year":"2013","journal-title":"PLoS One"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"503","DOI":"10.1017\/S0007114598001597","article-title":"Effects of red pepper added to high-fat and high-carbohydrate meals on energy metabolism and substrate utilization in Japanese women","volume":"80","author":"Yoshioka","year":"1998","journal-title":"Br. J. Nutr."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Topal, M., and G\u00fcl\u00e7in, \u0130. (2014). Rosmarinic acid: A potent carbonic anhydrase isoenzymes inhibitor. Turk. J. Chem.","DOI":"10.3906\/kim-1403-5"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1089\/jmf.2010.0197","article-title":"Antioxidant activity of eugenol-a structure and activity relationship study","volume":"14","year":"2011","journal-title":"J. Med. Food"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1007\/s00204-011-0774-2","article-title":"Antioxidant activity of food constituents-An overview","volume":"86","year":"2012","journal-title":"Arch. Toxicol."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"2328","DOI":"10.3390\/molecules18022328","article-title":"Techniques for analysis of plant phenolic compounds","volume":"18","author":"Khoddami","year":"2013","journal-title":"Molecules"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1111\/j.1747-0285.2010.00965.x","article-title":"Carbonic anhydrase inhibitors: Inhibition of human erythrocyte isozymes I and II with a series of phenolic acids","volume":"75","author":"Supuran","year":"2010","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1583","DOI":"10.1016\/j.bmcl.2008.01.077","article-title":"Carbonic anhydrase inhibitors. Interactions of phenols with the 12 catalytically active mammalian isoforms (CA I-XIV)","volume":"18","author":"Innocenti","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2159","DOI":"10.1016\/j.bmc.2010.01.076","article-title":"Carbonic anhydrase inhibitors: Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids","volume":"18","author":"Innocenti","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"7424","DOI":"10.1016\/j.bmc.2008.06.013","article-title":"Carbonic anhydrase inhibitors: Inhibition of mammalian isoforms I\u2013XIV with a series of substituted phenols including paracetamol and salicylic acid","volume":"16","author":"Innocenti","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"14","DOI":"10.1016\/j.bmc.2009.11.021","article-title":"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","volume":"18","author":"Davis","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3659","DOI":"10.1021\/ja00087a086","article-title":"Phenol as a carbonic anhydrase inhibitor","volume":"116","author":"Nair","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"3207","DOI":"10.1016\/j.bmc.2009.01.067","article-title":"Carbonic anhydrase inhibitors: Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols","volume":"17","author":"Senturk","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"8514","DOI":"10.1073\/pnas.0702899104","article-title":"Carbonic anhydrase XIV deficiency produces a functional defect in the retinal light response","volume":"104","author":"Ogilvie","year":"2007","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"7365","DOI":"10.1021\/bi9007512","article-title":"Apo-human carbonic anhydrase II revisited: Implications of the loss of a metal in protein structure, stability, and solvent network","volume":"48","author":"Avvaru","year":"2009","journal-title":"Biochemistry"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"150","DOI":"10.7813\/2075-4124.2013\/5-4\/A.21","article-title":"Caffeic acid phenethyl ester (CAPE): A potent carbonic anhydrase isoenzymes inhibitor","volume":"5","year":"2013","journal-title":"Int. J. Acad. Res."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.1248\/bpb.30.2257","article-title":"Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo","volume":"30","author":"Beydemir","year":"2007","journal-title":"Biol. Pharm. Bull."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1556\/avet.52.2004.4.4","article-title":"Effect of vitamin E on carbonic anhydrase enzyme activity in rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo","volume":"52","author":"ArasHisar","year":"2004","journal-title":"Acta Vet. Hung."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"685","DOI":"10.3109\/14756360903514164","article-title":"Synthesis and antioxidant properties of diphenylmethane derivative bromophenols including a natural product","volume":"25","author":"Menzek","year":"2010","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_54","first-page":"379","article-title":"Novel sulfamides as potential carbonic anhydrase isoenzymes inhibitors","volume":"21","author":"Akbaba","year":"2013","journal-title":"Bioorg. Med. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"354","DOI":"10.1002\/ardp.201300349","article-title":"Synthesis and carbonic anhydrase isoenzymes inhibitory effects of brominated diphenylmethanone and its derivatives","volume":"347","author":"Menzek","year":"2014","journal-title":"Arch. Pharm."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1080\/1475636040001704461","article-title":"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","volume":"20","author":"Hisar","year":"2005","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"680","DOI":"10.1038\/227680a0","article-title":"Cleavage of structural proteins during the assembly of the head of bacteriophage T4","volume":"227","author":"Laemmli","year":"1970","journal-title":"Nature"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"297","DOI":"10.1080\/1475636032000141890","article-title":"Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibition effects of some chemicals on the enzyme activity","volume":"20","author":"Oktay","year":"2005","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1080\/09712119.2005.9706791","article-title":"Effect of melatonin on glucose-6-phospate dehydrogenase from rainbow trout (Oncorhynchus mykiss) erythrocytes in vitro and in vivo","volume":"28","author":"Beydemir","year":"2005","journal-title":"J. Appl. Anim. Res."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1080\/14756360701474780","article-title":"The inhibitory effect of ethanol on carbonic anhydrase isoenzymes: In vivo and in vitro studies","volume":"23","author":"Beydemir","year":"2008","journal-title":"J. Enzyme Inhib. Med. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"4221","DOI":"10.1016\/S0021-9258(18)95800-X","article-title":"Esterase activities of human carbonic anhydrases B and C","volume":"242","author":"Verpoorte","year":"1967","journal-title":"J. Biol. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"3207","DOI":"10.1016\/j.bmc.2009.01.067","article-title":"Carbonic anhydrase inhibitors: Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols","volume":"17","author":"Supuran","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"783","DOI":"10.1002\/ardp.201300228","article-title":"Synthesis, antioxidant and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine related compounds","volume":"346","year":"2013","journal-title":"Arch. Pharm."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"5791","DOI":"10.1016\/j.bmc.2009.07.019","article-title":"Sildenafil is a strong activator of mammalian carbonic anhydrase isoforms I-XIV","volume":"17","author":"Coban","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1016\/0003-2697(76)90527-3","article-title":"A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding","volume":"72","author":"Bradford","year":"1976","journal-title":"Anal. Biochem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"320","DOI":"10.2174\/092986608784246506","article-title":"Purification and characterization of peroxidase from cauliflower (Brassica oleracea L.) buds","volume":"15","year":"2008","journal-title":"Protein Peptide Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2036","DOI":"10.1248\/bpb.31.2036","article-title":"Dantrolene inhibits human erythrocyte glutathione reductase","volume":"31","year":"2008","journal-title":"Biol. Pharm. Bull."},{"key":"ref_68","first-page":"299","article-title":"Synthesis and characterization of new chromogenic substrates for exoglycosidases: a-Glucosidase, a-mannosidase, and\u03b2-galactosidase","volume":"37","author":"Iga","year":"2013","journal-title":"Turk. J. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"658","DOI":"10.1021\/ja01318a036","article-title":"The determination of enzyme dissociation constants","volume":"56","author":"Lineweaver","year":"1934","journal-title":"Am. Chem. Soc."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1002\/ardp.201100272","article-title":"Synthesis and antioxidant properties of (3,4-dihydroxyphenyl)(2,3,4-trihydroxyphenyl)methanone and its derivatives","volume":"345","author":"Menzek","year":"2012","journal-title":"Arch. Pharm."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"5050","DOI":"10.1016\/j.bmcl.2010.07.038","article-title":"Carbonic anhydrase inhibitors: Antioxidant polyphenol natural products effectively inhibit mammalian isoforms I-XV","volume":"20","author":"Innocenti","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"4259","DOI":"10.1016\/j.bmcl.2011.05.071","article-title":"In vitro inhibition of \u03b1-carbonic anhydrase isozymes by some phenolic compounds","volume":"21","author":"Topal","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1016\/j.ejmech.2012.05.025","article-title":"Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols and their derivatives including natural products: Vidalol B","volume":"54","author":"Senturk","year":"2012","journal-title":"Eur. J. Med. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/19\/7\/10103\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:13:31Z","timestamp":1760217211000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/19\/7\/10103"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,7,10]]},"references-count":73,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2014,7]]}},"alternative-id":["molecules190710103"],"URL":"https:\/\/doi.org\/10.3390\/molecules190710103","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,7,10]]}}}