In silico and in vitro inhibition abilities of novel benzene sulfonamides on carbonic anhydrase and choline esterases

References

• DeTure, M. A.; Dickson, D. W. The Neuropathological Diagnosis of Alzheimer’s Disease. Mol. Neurodegener. 2019, 14, 32. DOI: 10.1186/s13024-019-0333-5.
   PubMed Web of Science ®Google Scholar
• Dincel, E. D.; Başoğlu‐Ünal, F.; Kuran, E. D.; Kayra, T.; Aydın, N.; Kanber, E.; Gülçin, İ.; Ulusoy‐Güzeldemirci, N. Design, Synthesis, and Evaluation of Novel Bistrifluoromethyl-Based Hydrazones as Dual İnhibitors of Acetylcholinesterase and Carbonic Anhydrase Enzymes for Alzheimer’s Disease. Chem. Biol. Drug Des. 2024, 103, e14482. DOI: 10.1111/cbdd.14482.
   PubMed Web of Science ®Google Scholar
• Abdoli, M.; Bonardi, A.; Supuran, C. T.; Žalubovskis, R. Investigation of Novel Alkyl/Benzyl (4-Sulphamoylphenyl)Carbamimidothioates as Carbonic Anhydrase İnhibitors. J. Enzyme Inhib. Med. Chem. 2023, 38, 2152811. DOI: 10.1080/14756366.2022.2152811.
   PubMed Web of Science ®Google Scholar
• Wang, S.; Blahut, M.; Wu, Y.; Philipkosky, K. E.; Outten, F. W. Communication between Binding Sites Is Required for YqjI Regulation of Target Promoters within the yqjH-yqjI Intergenic Region. J. Bacteriol. 2014, 196, 3199–3207. DOI: 10.1128/jb.01835-14.
   PubMed Web of Science ®Google Scholar
• Gocer, H.; Aslan, A.; Gülçin, İ.; Supuran, C. T. Spirobisnaphthalenes Effectively İnhibit Carbonic Anhydrase. J. Enzyme Inhib. Med. Chem. 2015, 31, 1–5. DOI: 10.3109/14756366.2015.1043298.
   PubMed Web of Science ®Google Scholar
• Çetinkaya, Y.; Göçer, H.; Göksu, S.; Gülçin, İ. Synthesis and Carbonic Anhydrase İsoenzymes I and II İnhibitory Effects of Novel Benzylamine Derivatives. J. Enzyme Inhib. Med. Chem. 2014, 29, 168–174. DOI: 10.3109/14756366.2012.763163.
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu, A.; Akbaba, Y.; Göçer, H.; Göksu, S.; Gülçin, İ.; Supuran, C. T. Novel Sulfamides as Potential Carbonic Anhydrase İsoenzymes İnhibitors. Bioorg. Med. Chem. 2013, 21, 1379–1385. DOI: 10.1016/j.bmc.2013.01.019.
   PubMed Web of Science ®Google Scholar
• Artunç, T.; Çetinkaya, Y.; Göçer, H.; Gülçin, İ.; Menzek, A.; Şahin, E.; Supuran, C. T. Synthesis of 4-[2-(3,4-Dimethoxybenzyl)Cyclopentyl]-1,2-Dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects. Chem. Biol. Drug Des. 2016, 87, 594–607. DOI: 10.1111/cbdd.12695.
   PubMed Web of Science ®Google Scholar
• Moi, D.; Vittorio, S.; Angeli, A.; Balboni, G.; Supuran, C. T.; Onnis, V. Investigation on Hydrazonobenzenesulfonamides as Human Carbonic Anhydrase I, II, IX and XII Inhibitors. Molecules 2023, 28, 91. DOI: 10.3390/molecules28010091.
   Web of Science ®Google Scholar
• Oztürk Sarikaya, S. B.; Topal, F.; Sentürk, M.; Gülçin, I.; Supuran, C. T. In Vitro İnhibition of α-Carbonic Anhydrase İsozymes by Some Phenolic Compounds. Bioorg. Med. Chem. Lett. 2011, 21, 4259–4262. DOI: 10.1016/j.bmcl.2011.05.071.
   PubMed Web of Science ®Google Scholar
• Taslimi, P.; Gülçin, İ.; Öztaşkın, N.; Çetinkaya, Y.; Göksu, S.; Alwasel, S. H.; Supuran, C. T. The Effects of Some Bromophenols on Human Carbonic Anhydrase İsoenzymes. J. Enzyme Inhib. Med. Chem. 2016, 31, 603–607. DOI: 10.3109/14756366.2015.1054820.
   PubMedGoogle Scholar
• Aksu, K.; Akıncıoğlu, H.; Akıncıoğlu, A.; Göksu, S.; Tümer, F.; Gülçin, İ. Synthesis of Novel Sulfamides İncorporating Phenethylamines and Determination of Their İnhibition Profiles against Some Metabolic Enzymes. Arch. Pharm. 2018, 351, 1800150. DOI: 10.1002/ardp.201800150.
   Web of Science ®Google Scholar
• Gokcen, T.; Al, M.; Topal, M.; Gulcin, I.; Ozturk, T.; Goren, A. C. Synthesis of Some Natural Sulphonamide Derivatives as Carbonic Anhydrase İnhibitors. Org. Commun. 2017, 10, 15–23. DOI: 10.25135/acg.oc.4.16.05.418.
   Web of Science ®Google Scholar
• Gök, N.; Akıncıoğlu, A.; Erümit Binici, E.; Akıncıoğlu, H.; Kılınç, N.; Göksu, S. Synthesis of Novel Sulfonamides with anti-Alzheimer and Antioxidant Capacities. Arch. Pharm. 2021, 354, 2000496. DOI: 10.1002/ardp.202000496.
   Web of Science ®Google Scholar
• Yıldırım, A.; Atmaca, U.; Keskin, A.; Topal, M.; Çelik, M.; Gülçin, İ.; Supuran, C. T. N-Acylsulfonamides Strongly İnhibit Human Carbonic Anhydrase İsoenzymes I and II. Bioorg. Med. Chem. 2015, 23, 2598–2605. DOI: 10.1016/j.bmc.2014.12.054.
   PubMed Web of Science ®Google Scholar
• Tugrak, M.; Gul, H. I.; Akincioglu, H.; Gulcin, I. New Chalcone Derivatives with Pyrazole and Sulfonamide Pharmacophores as Carbonic Anhydrase Inhibitors. LDDD. 2021, 18, 191–198. DOI: 10.2174/1570180817999201001160414.
   Google Scholar
• Akıncıoğlu, H.; Gülçin, İ. Potent Acetylcholinesterase Inhibitors: Potential Drugs for Alzheimer’s Disease. Mini Rev. Med. Chem. 2020, 20, 703–715. DOI: 10.2174/1389557520666200103100521.
   PubMed Web of Science ®Google Scholar
• Žnidaršič, N.; Štrbenc, M.; Grgurevič, N.; Snoj, T. Potential Revival of Cholinesterase İnhibitors as Drugs in Veterinary Medicine. Front. Vet. Sci. 2023, 10, 1125618. DOI: 10.3389/fvets.2023.1125618.
   PubMed Web of Science ®Google Scholar
• El-Sayed, N. A. E.; Farag, A. E. S.; Ezzat, M. A. F.; Akincioglu, H.; Gülçin, İ.; Abou-Seri, S. M. Design, Synthesis, in Vitro and in Vivo Evaluation of Novel Pyrrolizine-Based Compounds with Potential Activity as Cholinesterase İnhibitors and anti-Alzheimer’s Agents. Bioorg. Chem. 2019, 93, 103312. DOI: 10.1016/j.bioorg.2019.103312.
   PubMed Web of Science ®Google Scholar
• Davies, T. Q.; Tilby, M. J.; Skolc, D.; Hall, A.; Willis, M. C. Primary Sulfonamide Synthesis Using the Sulfinylamine Reagent N-Sulfinyl-O-(Tert-Butyl)Hydroxylamine, t-BuONSO. Org. Lett. 2020, 22, 9495–9499. DOI: 10.1021/acs.orglett.0c03505.
   PubMed Web of Science ®Google Scholar
• Batool, M.; Afzal, Z.; Junaid, H. M.; Solangi, A. R.; Hassan, A. Sulfonamides as Optical Chemosensors. Crit. Rev. Anal. Chem. 2022, 1–28. DOI: 10.1080/10408347.2022.2105135.
   PubMed Web of Science ®Google Scholar
• Tačić, A.; Nikolić, V.; Nikolić, L.; Savić, I. Antimikrobni Sulfonamidni Lekovi. Adv. Technol 2017, 6, 58–71. DOI: 10.5937/savteh1701058T.
   Google Scholar
• Supuran, C. T.; Briganti, F.; Tilli, S.; Chegwidden, W. R.; Scozzafava, A. Carbonic Anhydrase İnhibitors: Sulfonamides as Antitumor Agents? Bioorg. Med. Chem. 2001, 9, 703–714. DOI: 10.1016/S0968-0896(00)00288-1.
   PubMed Web of Science ®Google Scholar
• Gangapuram, M.; Mazzio, E.; Eyunni, S.; Soliman, K. F.; Redda, K. K. Synthesis and Biological Evaluation of Substituted N-[3-(1H-Pyrrol-1-Yl)Methyl]-1,2,5,6-Tetrahydropyridin-1-Yl]Benzamide/Benzene Sulfonamides as Anti-Inflammatory Agents. Arch. Pharm. 2014, 347, 360–369. DOI: 10.1002/ardp.201300379.
   PubMed Web of Science ®Google Scholar
• Chohan, Z. H.; Shad, H. A.; Supuran, C. T. Synthesis, Characterization and Biological Studies of Sulfonamide Schiff’s Bases and Some of Their Metal Derivatives. J. Enzyme Inhib. Med. Chem. 2012, 27, 58–68. DOI: 10.3109/14756366.2011.574623.
   PubMed Web of Science ®Google Scholar
• Owa, T.; Nagasu, T. Novel Sulphonamide Derivatives for the Treatment of Cancer. Expert Opin. Ther. Pat. 2000, 10, 1725–1740. DOI: 10.1517/13543776.10.11.1725.
   Web of Science ®Google Scholar
• Akıncıoğlu, A.; Topal, M.; Gülçin, İ.; Göksu, S. Novel Sulphamides and Sulphonamides Incorporating the Tetralin Scaffold as Carbonic Anhydrase and Acetylcholine Esterase Inhibitors. Arch. Pharm. 2014, 347, 68–76. DOI: 10.1002/ardp.201300273.
   PubMed Web of Science ®Google Scholar
• Ogden, R. C.; Flexner, C. W. Protease Inhibitors in AIDS Therapy. Marcel Dekker: New York, Basel, 2001.
   Google Scholar
• Lee, V. J. Anti-Gram-Positive Agents of Natural Product Origins, Volume 7, Comprehensive Medicinal Chemistry II. Ed: Taylor, J. B.; Triggle, D. J. Adesis, Inc. New Castle, DE, USA, 2007, 653–671.
   Google Scholar
• Göçer, H.; Akıncıoğlu, A.; Öztaşkın, N.; Göksu, S.; Gülçin, İ. Synthesis, Antioxidant, and Antiacetylcholinesterase Activities of Sulfonamide Derivatives of Dopamine-Related Compounds. Arch. Pharm. (Weinheim) 2013, 346, 783–792. DOI: 10.1002/ardp.201300228.
   PubMed Web of Science ®Google Scholar
• Mok, B. L.; J. The Synthesis of Functionalized Sulfonamides., PhD Thesis, Chemistry Department, University College, London, U.K, 2008.
   Google Scholar
• Keil, K.; Frerichs, V. A.; DiFrancesco, R.; Morse, G. Reverse Phase High-Performance Liquid Chromatography Method for the Analysis of Amprenavir, Efavirenz, Indinavir, Lopinavir, Nelfinavir and Its Active Metabolite (M8), Ritonavir, and Saquinavir in Heparinized Human Plasma. Ther. Drug Monit. 2003, 25, 340–346. DOI: 10.1097/00007691-200306000-00015.
   PubMed Web of Science ®Google Scholar
• Yan, B.; Peng, Z.; Xing, X.; Du, C. Glibenclamide İnduces Apoptosis by Activating Reactive Oxygen Species Dependent JNK Pathway in Hepatocellular Carcinoma Cells. Biosci. Rep. 2017, 37, BSR20170685. DOI: 10.1042/BSR20170685.
   PubMed Web of Science ®Google Scholar
• Han, T.; Goralski, M.; Gaskill, N.; Capota, E.; Kim, J.; Ting, T. C.; Xie, Y.; Williams, N. S.; Nijhawan, D. Anticancer Sulfonamides Target Splicing by İnducing RBM39 Degradation via Recruitment to DCAF15. Science 2017, 356, eaal3755. DOI: 10.1126/science.aal3755.
   PubMed Web of Science ®Google Scholar
• Sun, W.; Hu, X.; Xiang, Y.; Ye, N. Adsorption Behavior and Mechanism of Sulfonamides on Controllably Synthesized Covalent Organic Frameworks. Environ. Sci. Pollut. Res. 2022, 29, 18680–18688. DOI: 10.1007/s11356-021-17169-z.
   PubMed Web of Science ®Google Scholar
• Ovung, A.; Bhattacharyya, J. Sulfonamide Drugs: Structure, Antibacterial Property, Toxicity, and Biophysical İnteractions. Biophys. Rev. 2021, 13, 259–272. DOI: 10.1007/s12551-021-00795-9.
   PubMedGoogle Scholar
• DeBergh, J. R.; Niljianskul, N.; Buchwald, S. L. Synthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids. J. Am. Chem. Soc. 2013, 135, 10638–10641. DOI: 10.1021/ja405949a.
   PubMed Web of Science ®Google Scholar
• Scozzafava, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors. Arylsulfonylureido-and Arylureido-Substituted Aromatic and Heterocyclic Sulfonamides: Towards Selective Inhibitors of Carbonic Anhydrase Isozyme I. J. Enzyme Inhib. Med. Chem. 1999, 14, 343–363. DOI: 10.3109/14756369909030328.
   Web of Science ®Google Scholar
• Arslan, O. Inhibition of Bovine Carbonic Anhydrase by New Sulfonamide Compounds. Biochemistry. (Mosc) 2001, 66, 982–983. DOI: 10.1023/A:1012365424900.
   PubMed Web of Science ®Google Scholar
• Angeli, A.; Paoletti, N.; Supuran, C. T. Five-Membered Heterocyclic Sulfonamides as Carbonic Anhydrase Inhibitors. Molecules 2023, 28, 3220. DOI: 10.3390/molecules28073220.
   PubMed Web of Science ®Google Scholar
• Yamali, C.; Gul, H. I.; Cakir, T.; Demir, Y.; Gulcin, I. Aminoalkylated Phenolic Chalcones: Investigation of Biological Effects on Acetylcholinesterase and Carbonic Anhydrase I and II as Potential Lead Enzyme Inhibitors. LDDD. 2020, 17, 1283–1292. DOI: 10.2174/1570180817999200520123510.
   Google Scholar
• Site Map 3.5 User Manual. https://gohom.win/ManualHom/Schrodinger/Schrodinger_20152_docs/sitemap/sitemap_user_manual.pdf. (accessed 8 August, 2023).
   Google Scholar
• Göçer, H.; Akincioğlu, A.; Göksu, S.; Gülçin, İ.; Supuran, C. T. Carbonic Anhydrase and Acetylcholinesterase İnhibitory Effects of Carbamates and Sulfamoylcarbamates. J. Enzyme Inhib. Med. Chem. 2015, 30, 316–320. DOI: 10.3109/14756366.2014.928704.
   PubMed Web of Science ®Google Scholar
• Sherman, W.; Day, T.; Jacobson, M. P.; Friesner, R. A.; Farid, R. Novel Procedure for Modeling Ligand/Receptor Induced Fit Effects. J. Med. Chem. 2006, 49, 534–553. DOI: 10.1021/jm050540c.
   PubMed Web of Science ®Google Scholar
• Sotriffer, C. A. Accounting for Induced-Fit Effects in Docking: What is Possible and What is Not? Curr. Top. Med. Chem. 2011, 11, 179–191. DOI: 10.2174/156802611794863544.
   PubMed Web of Science ®Google Scholar
• Structure of human acetylcholinesterase in complex with dihydrotanshinone I. https://www.rcsb.org/structure/4m0e. (accessed 8 August, 2023).
   Google Scholar
• Cheung, J.; Gary, E. N.; Shiomi, K.; Rosenberry, T. L. Structures of Human Acetylcholinesterase Bound to Dihydrotanshinone I and Territrem B Show Peripheral Site Flexibility. ACS Med. Chem. Lett. 2013, 4, 1091–1096. DOI: 10.1021/ml400304w.
   PubMed Web of Science ®Google Scholar
• Human butyrylcholinesterase in complex with N-((1-(2,3-dihydro-1H-inden-2-yl)piperidin-3-yl)methyl)-N-(2-methoxyethyl)-2-naphthamide. https://www.rcsb.org/structure/4tpk. (accessed Aug. 8, 2023).
   Google Scholar
• Crystal structure of human carbonic anhydrase isozyme I with 2,3,5,6-Tetrafluoro-4-(propylthio)benzenesulfonamide. https://www.rcsb.org/structure/4wr7. (accessed Aug. 8, 2023).
   Google Scholar
• Three-dimensional structure of human carbonic anhydrase II in complex with 2-(But-2-yn-1-ylsulfamoyl)-4-sulfamoylbenzoicacid. https://www.rcsb.org/structure/5aml. (accessed Aug. 8, 2023).
   Google Scholar
• Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Adv. Drug Deliv. Rev 1997, 23, 3–25. DOI: 10.1016/j.addr.2012.09.019.
   Web of Science ®Google Scholar
• Xing, L.; Wang, X.; Cheng, C.; Zhu, R.; Liu, B.; Hu, Y. A Solvent-Controlled Highly Efficient Pd–C Catalyzed Hydrogenolysis of Benzaldehydes to Methylbenzenes via a Novel ‘Acetal Pathway’. Tetrahedron 2007, 63, 9382–9386. DOI: 10.1016/j.tet.2007.06.105.
   Web of Science ®Google Scholar
• Gülçin, İ.; Scozzafava, A.; Supuran, C. T.; Akıncıoğlu, H.; Koksal, Z.; Turkan, F.; Alwasel, S. The Effect of Caffeic Acid Phenethyl Ester (CAPE) on Metabolic Enzymes İncluding Acetylcholinesterase, Butyrylcholinesterase, Glutathione S-Transferase, Lactoperoxidase, and Carbonic Anhydrase İsoenzymes I, II, IX, and XII. J. Enzyme Inhib. Med. Chem. 2016, 31, 1095–1101. DOI: 10.3109/14756366.2015.1094470.
   PubMed Web of Science ®Google Scholar
• Ellman, G. L.; Courtney, K. D.; Andres, V.; Feather-Stone, R. M. A New and Rapid Colorimetric Determination of Acetylcholinesterase Activity. Biochem. Pharmacol. 1961, 7, 88–95. DOI: 10.1016/0006-2952(61)90145-9.
   PubMed Web of Science ®Google Scholar
• Verpoorte, J. A.; Mehta, S.; Edsall, J. T. Esterase Activities of Human Carbonic Anhydrases B and C. J. Biol. Chem. 1967, 242, 4221–4229. DOI: 10.1016/S0021-9258(18)95800-X.
   PubMed Web of Science ®Google Scholar
• Akıncıoğlu, A.; Göksu, S.; Naderi, A.; Akıncıoğlu, H.; Kılınç, N.; Gülçin, İ. Cholinesterases, Carbonic Anhydrase İnhibitory Properties and in Silico Studies of Novel Substituted Benzylamines Derived from Dihydrochalcones. Comput. Biol. Chem. 2021, 94, 107565. DOI: 10.1016/j.compbiolchem.2021.107565.
   PubMed Web of Science ®Google Scholar
• Orhan, F.; Akincioglu, H. Determination of Carbonic Anhydrase Enzyme Activity in Halophilic/Halotolerant Bacteria. Appl. Soil Ecol. 2020, 155, 103650. DOI: 10.1016/j.apsoil.2020.103650.
   Web of Science ®Google Scholar
• Schrödinger Release 2022-4. Maestro; Schrödinger, LLC, New York, 2022.
   Google Scholar
• Schrödinger Release 2022-4. Maestro; Protein Preparation, Wizard Schrödinger, LLC, New York, 2022.
   Google Scholar
• Schrödinger Release 2022-4. Maestro; SiteMap, Schrödinger, LLC, New York, 2022.
   Google Scholar
• Halgren, T. New Method for Fast and Accurate Binding-Site Identification and Analysis. Chem. Biol. Drug Des. 2007, 69, 146–148. DOI: 10.1111/j.1747-0285.2007.00483.x.
   PubMed Web of Science ®Google Scholar
• Schrödinger Release 2022-4. Maestro; LigPrep, Schrödinger, LLC, New York, 2022.
   Google Scholar
• Schrödinger Release 2022-4. Maestro; Induced Fit Docking protocol, Glide, Prime, Schrödinger, LLC, New York, 2022.
   Google Scholar
• Schrödinger Release 2022-4. Maestro; QikProp, Schrödinger, LLC, New York, 2022.
   Google Scholar