Determination of the inhibition profiles of pyrazolyl–thiazole derivatives against aldose reductase and α-glycosidase and molecular docking studies
Yeliz Demir
Department of Pharmacy Services, Nihat Delibalta Göle Vocational High School, Ardahan University, Ardahan, Turkey
Search for more papers by this authorParham Taslimi
Department of Biotechnology, Faculty of Science, Bartin University, Bartin, Turkey
Search for more papers by this authorCorresponding Author
Ümit M. Koçyiğit
Department of Basic Pharmaceutical Sciences, Division of Biochemistry, Faculty of Pharmacy, Cumhuriyet University, Sivas, Turkey
Correspondence Ümit M. Koçyiğit, Department of Basic Pharmaceutical Sciences, Division of Biochemistry, Faculty of Pharmacy, Cumhuriyet University, 58140-Sivas, Turkey.
Email: [email protected]
Search for more papers by this authorMusa Akkuş
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey
Search for more papers by this authorMuhammet Serhat Özaslan
Department of Pharmacy Services, Nihat Delibalta Göle Vocational High School, Ardahan University, Ardahan, Turkey
Search for more papers by this authorHatice Esra Duran
Department of Biochemistry, Medical School, Kafkas University, Kars, Turkey
Search for more papers by this authorYakup Budak
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey
Search for more papers by this authorBurak Tüzün
Department of Chemistry, Faculty of Science, Cumhuriyet University, Sivas, Turkey
Search for more papers by this authorMeliha B. Gürdere
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey
Search for more papers by this authorMustafa Ceylan
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey
Search for more papers by this authorSeyithan Taysi
Department of Biochemistry and Clinical Biochemistry, Medical School, Gaziantep University, Gaziantep, Turkey
Search for more papers by this authorİlhami Gülçin
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey
Search for more papers by this authorŞükrü Beydemir
Department of Biochemistry, Faculty of Pharmacy, Anadolu University, Eskişehir, Turkey
The Rectorate of Bilecik Şeyh Edebali University, Bilecik, Turkey
Search for more papers by this authorYeliz Demir
Department of Pharmacy Services, Nihat Delibalta Göle Vocational High School, Ardahan University, Ardahan, Turkey
Search for more papers by this authorParham Taslimi
Department of Biotechnology, Faculty of Science, Bartin University, Bartin, Turkey
Search for more papers by this authorCorresponding Author
Ümit M. Koçyiğit
Department of Basic Pharmaceutical Sciences, Division of Biochemistry, Faculty of Pharmacy, Cumhuriyet University, Sivas, Turkey
Correspondence Ümit M. Koçyiğit, Department of Basic Pharmaceutical Sciences, Division of Biochemistry, Faculty of Pharmacy, Cumhuriyet University, 58140-Sivas, Turkey.
Email: [email protected]
Search for more papers by this authorMusa Akkuş
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey
Search for more papers by this authorMuhammet Serhat Özaslan
Department of Pharmacy Services, Nihat Delibalta Göle Vocational High School, Ardahan University, Ardahan, Turkey
Search for more papers by this authorHatice Esra Duran
Department of Biochemistry, Medical School, Kafkas University, Kars, Turkey
Search for more papers by this authorYakup Budak
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey
Search for more papers by this authorBurak Tüzün
Department of Chemistry, Faculty of Science, Cumhuriyet University, Sivas, Turkey
Search for more papers by this authorMeliha B. Gürdere
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey
Search for more papers by this authorMustafa Ceylan
Department of Chemistry, Faculty of Arts and Sciences, Gaziosmanpasa University, Tokat, Turkey
Search for more papers by this authorSeyithan Taysi
Department of Biochemistry and Clinical Biochemistry, Medical School, Gaziantep University, Gaziantep, Turkey
Search for more papers by this authorİlhami Gülçin
Department of Chemistry, Faculty of Science, Atatürk University, Erzurum, Turkey
Search for more papers by this authorŞükrü Beydemir
Department of Biochemistry, Faculty of Pharmacy, Anadolu University, Eskişehir, Turkey
The Rectorate of Bilecik Şeyh Edebali University, Bilecik, Turkey
Search for more papers by this authorAbstract
Aldose reductase (AR) is the first and rate-limiting enzyme of the polyol pathway, which converts glucose to sorbitol in an NADPH-dependent reaction. α-Glycosidase breaks down starch and disaccharides to glucose. Hence, inhibition of these enzymes can be regarded a considerable approach in the treatment of diabetic complications. AR was purified from sheep liver using simple chromatographic methods. The inhibitory effects of pyrazolyl–thiazoles ((3aR,4S,7R,7aS)-2-(4-{1-[4-(4-bromophenyl)thiazol-2-yl]-5-(aryl)-4,5-dihydro-1H-pyrazol-3-yl}phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives; 3a–i) on AR and α-glycosidase enzymes were investigated. All compounds showed a good inhibitory action against AR and α-glycosidase. Among these compounds, compound 3d exhibited the best inhibition profiles against AR, with a Ki value of 7.09 ± 0.19 µM, whereas compound 3e showed the lowest inhibition effects, with a Ki value of 21.89 ± 1.87 µM. Also, all compounds showed efficient inhibition profiles against α-glycosidase, with Ki values in the range of 0.43 ± 0.06 to 2.30 ± 0.48 µM, whereas the Ki value of acarbose was 12.60 ± 0.78 µM. Lastly, molecular modeling approaches were implemented to predict the binding affinities of compounds against AR and α-glycosidase. In addition, the ADME analysis of the molecules was performed.
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