title: Synthesis, carbonic anhydrase I and II isoenzymes inhibition properties, and antibacterial activities of novel tetralone-based 1,4-benzothiazepine derivatives.
abstract: Benzothiazepine compounds have a wide range of applications such as antibacterial, antidepressants, anticonvulsants, antihypertensives, antibiotics, antifungal, hypnotic, enzyme inhibitors, antitumor, anticancer and anti-HIV agents. In this study, the synthesis of novel tetralone-based benzothiazepine derivatives (1-16) and their in vitro antibacterial activity and human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibitory effects were investigated. Both isoenzymes were purified by sepharose-4B-l-tyrosine-sulfanilamide affinity chromatography from fresh human red blood cells. All compounds demonstrated the low nanomolar inhibitory effects on both isoenzymes using esterase activity. Benzothiazepine derivative 2 demonstrated the best hCA I inhibitory effect with Kivalue of 18.19 nM. Also, benzothiazepine derivative 7 showed the best hCA II inhibitory effect with Kivalue of 11.31 nM. On the other hand, acetazolamide clinically used as CA inhibitor, showed Kivalue of 19.92 nM against hCA I and 33.60 nM against hCA II, respectively.
authors: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, 60250, Turkey.
authors: Mustafa
authors: M
authors: Ceylan
authors: Cumhuriyet University,, Vocational School of Health Services, Sivas, 58140, Turkey.
authors: Umit M
authors: UM
authors: Kocyigit
authors: Department of Biology, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, 60250, Turkey.
authors: Necibe Canan
authors: NC
authors: Usta
authors: Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, 60250, Turkey.
authors: Belma
authors: B
authors: Gürbüzlü
authors: Department of Solhan School of Health Services, Bingol University, Bingol, 12000, Turkey.
authors: Yusuf
authors: Y
authors: Temel
authors: Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia.
authors: Saleh H
authors: SH
authors: Alwasel
authors: Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia.|Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, 25240, Turkey.
authors: İlhami
authors: İ
authors: Gülçin
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D024401:Carbonic Anhydrase I / Q000037:antagonists & inhibitors / Q000302:isolation & purification; D024402:Carbonic Anhydrase II / Q000037:antagonists & inhibitors / Q000302:isolation & purification; D002257:Carbonic Anhydrase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D004912:Erythrocytes / Q000201:enzymology; D006801:Humans; D044024:Tetralones / Q000138:chemical synthesis / Q000494:pharmacology*; D013841:Thiazepines / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D002257:Carbonic Anhydrase Inhibitors; D044024:Tetralones; D013841:Thiazepines; D024401:Carbonic Anhydrase I; D024402:Carbonic Anhydrase II
keywords: Antibacterial activity; Benzothiazepine; Carbonic anhydrase; Enzyme inhibition; Enzyme purification