title: Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: an in vitro study.
abstract: Two cinnamyl-substituted phloroglucinols, 4-p-methoxycinnamyl phloroglucinol (9) and 4,6-bis-p-methoxycinnamyl phloroglucinol (10) were synthesized. Two carbonic anhydrases, human carbonic anhydrase I and II (hCA I and II), were purified. Kinetic interactions between these isozymes with 9 and 10 were investigated. These new compounds exhibited inhibitory effects on the hCA I and II enzymes' activity in vitro. The combination of the inhibitory effects of both phloroglucinol and p-coumaric acid groups in a single compound was explored. However, relative to the inhibitory effects of the two groups separately, compounds 9 and 10 demonstrated comparable inhibitory effects. More effective inhibitors of CAs could be created by testing these compounds on other CA isozymes.
authors.affiliation: a Tercan Vocational High School, Erzincan University , Tercan-Erzincan , Turkey.|b Department of Biochemistry , Faculty of Pharmacy, Erzincan University , Erzincan , Turkey.
authors.forename: Serdar
authors.initials: S
authors.lastname: Burmaoğlu
authors.affiliation: c Department of Chemistry , Faculty of Science, Atatürk University , Erzurum , Turkey , and.
authors.forename: Esra
authors.initials: E
authors.lastname: Dilek
authors.affiliation: b Department of Biochemistry , Faculty of Pharmacy, Erzincan University , Erzincan , Turkey.
authors.forename: Ali Osman
authors.initials: AO
authors.lastname: Yılmaz
authors.affiliation: d Neurofarba Department, Section of Pharmaceutical and Nutriceutical Sciences, Universita degli Studi di Firenze , Sesto Fiorentino , Florence , Italy.
authors.forename: Claudiu T
authors.initials: CT
authors.lastname: Supuran
mesh_terms: D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors* / Q000302:isolation & purification / Q000378:metabolism; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors* / Q000302:isolation & purification / Q000378:metabolism; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002846:Chromatography, Affinity; D002934:Cinnamates / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000201:enzymology; D006801:Humans; D066298:In Vitro Techniques; D007527:Isoenzymes / Q000037:antagonists & inhibitors / Q000378:metabolism; D015394:Molecular Structure; D010696:Phloroglucinol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D002257:Carbonic Anhydrase Inhibitors; D002934:Cinnamates; D007527:Isoenzymes; C029010:cinnamic acid; D010696:Phloroglucinol; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Enzyme inhibition, human CAI, human CAII, phloroglucinol, synthesis