Synthesis and In Vitro Human Carbonic Anhydrase I and II Inhibition Properties of Some Novel Hydrazone Compounds Containing an Aryl Sulfonate Moiety

Yıl 2022, , 659 - 669, 31.08.2022

Reşit Çakmak

https://doi.org/10.18185/erzifbed.1132001

Cited By: 1

Öz

The aim of this research was to evaluate the enzyme inhibitory potential of some new hydrazone derivatives bearing an aryl sulfonate moiety against the human carbonic anhydrase isoenzymes I and II (hCA I and II), which were attained from commercial suppliers. In the current study, the structures of targeted molecules (5-8) were characterized by some spectroscopic techniques. The inhibition capacities of the compounds on hCA I and II activities were examined by employing the esterase activity method under in vitro conditions. The IC50 values of the tested molecules were determined in the range of 15.7-135.2 µM against hCA I and in the range of 13.5-76.3 µM against hCA II. Among them, compound 7 exhibited the highest activity against both hCA I and II. The inhibitory activity results of all tested compounds were also compared to the standard drug Acetazolamide (AAZ). It was established that some of the tested molecules showed the inhibitory activities close to AAZ.

Anahtar Kelimeler

Aryl sulfonate, hydrazone compound, enzyme inhibitory, human carbonic anhydrase

Teşekkür

I would like to thank Batman University and Ağrı İbrahim Çecen University for their laboratory support to this study. On the other hand, I would like to thank Prof. Dr. Murat Şentürk for enabling me to benefit from the laboratory facilities. The author funded this study.

Bir Aril Sülfonat Parçası İçeren Bazı Yeni Hidrazon Bileşiklerinin Sentezi ve İn Vitro İnsan Karbonik Anhidraz I ve II İnhibisyon Özellikleri

Öz

Kaynakça

• Gul, H. I., Kucukoglu, K., Yamali, C., Bilginer, S., Yuca, H., Ozturk, I., Taslimi, P., Gulcin, I., Supuran, C. T. 2016. “Synthesis of 4-(2-substituted hydrazinyl) benzenesulfonamides and their carbonic anhydrase inhibitory effects”. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(4), 568-573.
• Ayvaz, S., Çankaya, M., Atasever, A., Altuntas, A. 2013. “2-Amino-3-cyanopyridine derivatives as carbonic anhydrase inhibitors”. Journal of Enzyme Inhibition and Medicinal Chemistry, 28(2), 305-310.
• Çankaya, M., Kuzucu, M. 2015. “Effect of Some Drugs on Sheep Liver Carbonic Anhydrase I and II”. Erzincan University Journal of Science and Technology, 8(2), 201-212.
• Arslan, T., Türkoğlu, E. A., Şentürk, M., Supuran, C. T. 2016. “Synthesis and carbonic anhydrase inhibitory properties of novel chalcone substituted benzenesulfonamides”. Bioorganic & Medicinal Chemistry Letters, 26(24), 5867-5870.
• Alper Türkoğlu, E., Şentürk, M., Supuran, C. T., Ekinci, D. 2017. “Carbonic anhydrase inhibitory properties of some uracil derivatives”. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 74-77.
• Işık, S., Vullo, D., Durdagi, S., Ekinci, D., Şentürk, M., Çetin, A., Şentürk, E., Supuran, C. T. 2015. “Interaction of carbonic anhydrase isozymes I, II, and IX with some pyridine and phenol hydrazinecarbothioamide derivatives”. Bioorganic & Medicinal Chemistry Letters, 25(23), 5636-5641.
• Balaydın, H. T., Şentürk, M., Menzek, A. 2012. “Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives”. Bioorganic & Medicinal Chemistry Letters, 22(3), 1352-1357.
• Fidan, I., Salmas, R. E., Arslan, M., Şentürk, M., Durdagi, S., Ekinci, D., Şentürk, E., Coşgun, S., Supuran, C. T. 2015. “Carbonic anhydrase inhibitors: Design, synthesis, kinetic, docking and molecular dynamics analysis of novel glycine and phenylalanine sulfonamide derivatives”. Bioorganic & Medicinal Chemistry, 23(23), 7353-7358.
• Dilek, E., Çankaya, M., Ezmeci, T., Sunar, M., Çoban, T. A.2017. “Investigation in vitro effects of rivastigmine and galantamine used to treatment of Alzheimer's disease on CA isozymes I and II”. Erzincan University Journal of Science and Technology, 10(1), 1-10.
• Tas, M., Şentürk, E., Ekinci, D., Demirdag, R., Comakli, V., Bayram, M., Akyüz, M., Şentürk, M., Supuran, C. T. 2019. “Comparison of blood carbonic anhydrase activity of athletes performing interval and continuous running exercise at high altitude”. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1), 218-223.
• Coban, T. A., Beydemir, Ş., Gülçin, İ., Ekinci, D. 2007. “Morphine inhibits erythrocyte carbonic anhydrase in vitro and in vivo”. Biological and Pharmaceutical Bulletin, 30(12), 2257-2261.
• Göçer, H., Akincioğlu, A., Göksu, S., Gülçin, İ., Supuran, C. T. 2015. “Carbonic anhydrase and acetylcholinesterase inhibitory effects of carbamates and sulfamoylcarbamates”. Journal of Enzyme Inhibition and Medicinal Chemistry, 30(2), 316-320.
• Topal, F., Aksu, K., Gulcin, I., Tümer, F., Goksu, S. 2021. “Inhibition profiles of some symmetric sulfamides derived from phenethylamines on human carbonic anhydrase I, and II isoenzymes”. Chemistry & Biodiversity, 18(10), e2100422.
• De Simone, G., Pizika, G., Monti, S. M., Di Fiore, A., Ivanova, J., Vozny, I., Trapencieris, P., Zalubovskis, R., Alterio, V. 2014. “Hydrophobic substituents of the phenylmethylsulfamide moiety can be used for the development of new selective carbonic anhydrase inhibitors”. Biomed Research International, 2014.
• Khloya, P., Ceruso, M., Ram, S., Supuran, C. T., Sharma, P. K. 2015. “Sulfonamide bearing pyrazolylpyrazolines as potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII”. Bioorganic & Medicinal Chemistry Letters, 25(16), 3208-3212.
• Kose, L. P., Gulcin, İ., Yıldırım, A., Atmaca, U., Çelik, M., Alwasel, S. H., Supuran, C. T. 2016. “The human carbonic anhydrase isoenzymes I and II inhibitory effects of some hydroperoxides, alcohols, and acetates”. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(6), 1248-1253.
• Supuran, C. T. 2011. “Carbonic anhydrase inhibition with natural products: novel chemotypes and inhibition mechanisms”. Molecular Diversity, 15(2), 305-316.
• Supuran, C. T. 2016. “Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors”. Expert Opinion on Drug Metabolism & Toxicology, 12(4), 423-431.
• Pichake, J., Kharkar, P. S., Ceruso, M., Supuran, C. T., Toraskar, M. P. 2014. “Carbonic anhydrase inhibitors: design, synthesis, and biological evaluation of novel sulfonyl semicarbazide derivatives”. ACS Medicinal Chemistry Letters, 5(7), 793-796.
• Çakmak, R., Başaran, E., Şentürk, M. 2022. “Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors”. Archiv der Pharmazie, 355(4), 2100430.
• Demirdağ, R., Çomaklı, V., Şentürk, M., Ekinci, D., Küfrevioğlu, Ö. İ., Supuran, C. T. 2013. “Purification and characterization of carbonic anhydrase from sheep kidney and effects of sulfonamides on enzyme activity”. Bioorganic & Medicinal Chemistry, 21(6), 1522-1525.
• Büyükkidan, N., Büyükkidan, B., Bülbül, M., Kasimoğullari, R., Serdar, M., Mert, S. 2013. “Synthesis and characterisation of novel Co (II) complexes of pyrazole carboxylate derivated of sulfonamide as carbonic anhydrase inhibitors”. Journal of Pharmacy and Pharmacology, 65(3), 363-369.
• Kamalı, A., Çakmak, R., Boğa, M. 2022. “Anticholinesterase and antioxidant activities of novel heterocyclic Schiff base derivatives containing an aryl sulfonate moiety”. Journal of the Chinese Chemical Society, 69(4), 731-743.
• [ Başaran, E. 2021. “Some aryl sulfonyl ester-based heterocyclic schiff bases: synthesis, structure elucidation and antioxidant activity”. Journal of the Institute of Science and Technology, 11(4), 2967-2978.
• Başaran, E., Çakmak, R., Akkoç, S., Kaya, S. 2022. “Combined experimental and theoretical analyses on design, synthesis, characterization, and in vitro cytotoxic activity evaluation of some novel imino derivatives containing pyrazolone ring”. Journal of Molecular Structure, 1265, 133427.
• Freudenberg, K., Hess, H. 1926. “Ein Verfahren zur Kennzeichnung verschiedenartiger Hydroxylgruppen. Seine Anwendung auf das Lignin”. Justus Liebigs Annalen der Chemie, 448(1), 121-133.
• Piller, F. M., Metzger, A., Schade, M. A., Haag, B. A., Gavryushin, A., Knochel, P. 2009. “Preparation of polyfunctional arylmagnesium, arylzinc, and benzylic zinc reagents by using magnesium in the presence of LiCl”. Chemistry-A European Journal, 15(29), 7192-7202.
• Collado, D., Perez-Inestrosa, E., Suau, R., Navarrete, J. T. L. 2006. “Regioselective hydroxylation of phenols by simultaneous photochemical generation of phenol cation-radical and hydroxyl radical”. Tetrahedron, 62(12), 2927-2935.
• Lei, X., Jalla, A., Abou Shama, M. A., Stafford, J. M., Cao, B. 2015. “Chromatography-free and eco-friendly synthesis of aryl tosylates and mesylates”. Synthesis, 47(17), 2578-2585.
• Başaran, E., Haşimi, N., Çakmak, R., Çınar, E. 2022. “Synthesis, structural characterization, and biological evaluation of some hydrazone compounds as potential antioxidant agents”. Russian Journal of Bioorganic Chemistry, 48(1), 143-152.
• Çakmak, R., Başaran, E., Kaya, S., Erkan, S. 2022. “Synthesis, spectral characterization, chemical reactivity and anticancer behaviors of some novel hydrazone derivatives: experimental and theoretical insights”. Journal of Molecular Structure, 1253, 132224.
• Verpoorte, J. A., Mehta, S., Edsall, J. T. 1967. “Esterase activities of human carbonic anhydrases B and C”. Journal of Biological Chemistry, 242(18), 4221-4229.
• Altıntop, M. D., Sever, B., Özdemir, A., Kucukoglu, K., Onem, H., Nadaroglu, H., Kaplancıklı, Z. A. 2017. “Potential inhibitors of human carbonic anhydrase isozymes I and II: Design, synthesis and docking studies of new 1, 3, 4-thiadiazole derivatives”. Bioorganic & Medicinal Chemistry, 25(13), 3547-3554.
• Verma, G., Marella, A., Shaquiquzzaman, M., Akhtar, M., Ali, M. R., Alam, M. M. 2014. “A review exploring biological activities of hydrazones”. Journal of Pharmacy & Bioallied Sciences, 6(2), 69.
• Bhaskar, R., Salunkhe, N., Yaul, A., Aswar, A. 2015. “Bivalent transition metal complexes of ONO donor hydrazone ligand: Synthesis, structural characterization and antimicrobial activity”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 151, 621-627.
• Rollas, S., Güniz Küçükgüzel, Ş. 2007. “Biological activities of hydrazone derivatives”. Molecules, 12(8), 1910-1939.
• Altıntop, M. D., Özdemir, A., Turan-Zitouni, G., Ilgın, S., Atlı, Ö., İşcan, G., Kaplancıklı, Z. A. 2012. “Synthesis and biological evaluation of some hydrazone derivatives as new anticandidal and anticancer agents”. European Journal of Medicinal Chemistry, 58, 299-307.
• Kucukoglu, K., Gul, H. I., Taslimi, P., Gulcin, I., Supuran, C. T. 2019. “Investigation of inhibitory properties of some hydrazone compounds on hCA I, hCA II and AChE enzymes”. Bioorganic Chemistry, 86, 316-321.
• Sharma, V., Kumar, R., Bua, S., Supuran, C. T., Sharma, P. K. 2019. “Synthesis of novel benzenesulfonamide bearing 1, 2, 3-triazole linked hydroxy-trifluoromethylpyrazolines and hydrazones as selective carbonic anhydrase isoforms IX and XII inhibitors”. Bioorganic Chemistry, 85, 198-208.
• Tawfik, H. O., Petreni, A., Supuran, C. T., El-Hamamsy, M. H. 2022. “Discovery of new carbonic anhydrase IX inhibitors as anticancer agents by toning the hydrophobic and hydrophilic rims of the active site to encounter the dual-tail approach”. European Journal of Medicinal Chemistry, 232, 114190.