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Exploring Novel Schiff Base Compounds Derived from Benzothiophene-3- carboxaldehyde Hydrazones: In vitro and In silico Evaluation as Potential Inhibitors of Cholinesterases and Carbonic Anhydrases I-II

Yıl 2024, Cilt: 17 Sayı: 1, 174 - 195, 28.03.2024

Şule Gürsoy Zeynep Çaka Nagihan Faydalı Hanif Sirinzade Esra Dilek

https://doi.org/10.18185/erzifbed.1377310

Öz

In this study, inhibitions of some cytosolic enzymes were evaluated. Inhibitors of these enzymes can help illuminate and treat many related diseases (Alzhaimer, Parkinson's, Glaucoma, etc.). It is aimed to minimize drug side effects with multiple effects in one molecule. For this purpose in vitro effects of two benzothiophene Schiff bases on cholinesterases (AChE and BuChE) and human carbonic anhydrase isoforms (CAI and CAII) were investigated. Molecular modeling studies were carried out to elucidate the inhibition mechanism of two effective compounds on these enzymes. Then, two benzothiophene Schiff bases (1a and 1b compounds) were tested in vitro on these enzymes. The in vitro study results supported the in silico study results. Obtained results revealed that the benzothiophene derivatives inhibited the enzymes significantly. Ki values for CAI isoenzyme were determined to be in the range of 58.82 ± 7.96-126.28 ± 26.22 nM; for the CAII isoenzyme in the range of 27.86 ± 3.76-74.30 ± 7.89 nM; for acetylcholinesterase in the range of 1.31 ± 0.39-2.16 ± 1.01 nM; for butyrylcholinesterase in the range of 1.80 ± 0.27-2.01 ± 1.67 nM. Compared to the AZA control compound, 1b has demonstrated more strong inhibitory effect against CAI and CAII. Wherease compared with other control compound Tacrine, both compounds showed more potent inhibitory effect for cholinesterases (AChE and BuChE).

Anahtar Kelimeler

Benzothiophene Schiff bases cholinesterases carbonic anhydrase inhibition.

Destekleyen Kurum

2209-A University Students Research Projects Support Program 2021, 2 semesters, carried out by the TÜBITAK Scientist Support Programs Presidency (BIDEB)

Proje Numarası

1919B012109379

Kaynakça

  • [1]. Deka S, Mohan S, Saravanan J, Kakati M, Talukdar A, Sahariah BJ, Dey BK and Sarma RK (2012) Syntheses, characterization and in-vitro anti-Inflammatory activity of some novel thiophenes, Maced. J. Med. Sci. 5:159–163 DOI: org/10.3889/MJMS.1957-5773.2012.0225.
  • [2]. Abbas S, Hussain M, Ali S, Parvez M, Raza A, Haider A and Iqbal J (2013) Structural, enzyme inhibition, antibacterial and DNA protection studies of organotin (IV) derivatives of thiophene-2-carboxylic acid, J. Organometallic Chem. 724:255–261 https://doi.org/10.1016/j.jorganchem.2012.11.033
  • [3]. Asiri AM and Khan SA (2011) Synthesis and antibacterial activities of a bis-chalcone derived fromthiophene and its bis-cyclized products, Molecules 16:523–531. https://doi.org/10.3390/molecules16010523
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  • [5]. Rashad AE, Shamroukh AH, Abdel-Megeid RE, Mostafa A, El-Shesheny R, Kandeil A, Ali MA and Banert K (2010) Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for anti-avian influenza virus (H5N1) activity, Eur. J. Med.Chem. 45:5251–5257. https://doi.org/10.1016/j.ejmech.2010.08.044
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  • [8]. Aziz A, Salem AE, Sayed MA, Aboaly MM (2012). Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M(II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2). Journal of Molecular Structure, 1010:130-138. https://doi.org/10.1016/j.molstruc.2011.11.043
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  • [10]. Lam PL, Lee KKH, Kok SHL, Gambari R, Lam KH, Ho CL, Ma X, Lo YH, Wong WY, Dong QC, Bian ZX, Chui CH (2016), Antifungal study of substituted 4- pyridylmethylene-4’-aniline Schiff bases, RSC Adv., 106:104575-104581. https://doi.org/10.1039/C6RA20186E
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  • [19]. Unver Y, Unlüer D, Direkel S, Durdaği S. (2020) Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies. Turk J Chem. 44(4):1164-1176. https://doi.org/10.3906/kim-2004-78
  • [20]. Puthran D, Poojary B, Nayak SG, Purushotham N, Bhat M, Hedge H (2020) Novel Schiff bases–based thiophenes: Design, synthesisand biological evaluation. J Chin Chem Soc. 67:1278–1288. https://doi.org/10.1002/jccs.201900388
  • [21]. Langerman et al. (2020) Recent Advances in Acetylcholinesterase Inhibitors and Their Potential Applications in Central Nervous System Disorders. ACS Chemical Neuroscience 11(13): 1825-1836. https://doi.org/10.1021/acschemneuro.0c00029
  • [22]. Supuran CT (2010). Carbonic anhydrase inhibitors. Bioorganic & Medicinal Chemistry Letters, 20(12): 3467-3474. https://doi.org/10.1016/j.bmcl.2010.05.009
  • [23]. Zverova M. (2018) Alzheimer’s disease and blood-based biomarkers–potential contexts of use. Neuropsychiatric disease and treatment. 14:1877-1882. https://doi.org/10.2147/NDT.S172285
  • [24]. Zverova M. (2019) Clinical aspects of Alzheimer's disease. Clinical biochemistry. 72:3-6 https://doi.org/10.1016/j.clinbiochem.2019.04.015
  • [25]. Rezazadeh et al. (2020) A Review of Acetylcholinesterase Inhibitors as Alzheimer’s Disease Therapeutics. Neurotherapeutics 17(1): 53-77. https://doi.org/10.1007/s13311-019-00781-6
  • [26]. Sun MK and Alkon DL (2002) Carbonic anhydrase gating of attention: memory therapy and enhancement Trends Pharmacol. Sci., 23, 83-89. https://doi.org/10.1016/S0165-6147(02)01899-0
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  • [28]. Kidwai M, Negı N, Gupta S.D. (1994) Synthesis and antifertility activity of 1,5- diaryl-3(3’indolyl) formazans. Chem Pharm Bull (Tokyo) 42(11): 2363-64. https://doi.org/10.1248/cpb.42.2363
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  • [30]. Gao H, Jiang Y, Zhan J, Sun Y. (2021) Pharmacophore-based drug design of AChE and BChE dual inhibitors as potential anti-Alzheimer's disease agents. Bioorg Chem.114:105149. https://doi.org/10.1016/j.bioorg.2021.105149
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  • [33]. Lill MA, Danielson ML. (2011) Computer-aided drug design platform using PyMOL. J Comput Aided Mol Des. 25(1): 13-19. https://doi.org/10.1007/s10822-010-9395-8
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  • [37]. Bayram E, Senturk M, Kufrevioglu OI, Supuran CT (2008) In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg. Med. Chem., 6, 9101-9105. https://doi.org/10.1016/j.bmc.2008.09.028
  • [38]. Burmaoğlu S, Dilek E, Yılmaz AO, Supuran CT (2016) Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: an in vitro study. J. Enzyme Inhib. Med. Chem., 31(sup2):208-212. https://doi.org/10.1080/14756366.2016.1181626
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Yıl 2024, Cilt: 17 Sayı: 1, 174 - 195, 28.03.2024

Şule Gürsoy Zeynep Çaka Nagihan Faydalı Hanif Sirinzade Esra Dilek

https://doi.org/10.18185/erzifbed.1377310

Öz

Proje Numarası

1919B012109379

Kaynakça

  • [1]. Deka S, Mohan S, Saravanan J, Kakati M, Talukdar A, Sahariah BJ, Dey BK and Sarma RK (2012) Syntheses, characterization and in-vitro anti-Inflammatory activity of some novel thiophenes, Maced. J. Med. Sci. 5:159–163 DOI: org/10.3889/MJMS.1957-5773.2012.0225.
  • [2]. Abbas S, Hussain M, Ali S, Parvez M, Raza A, Haider A and Iqbal J (2013) Structural, enzyme inhibition, antibacterial and DNA protection studies of organotin (IV) derivatives of thiophene-2-carboxylic acid, J. Organometallic Chem. 724:255–261 https://doi.org/10.1016/j.jorganchem.2012.11.033
  • [3]. Asiri AM and Khan SA (2011) Synthesis and antibacterial activities of a bis-chalcone derived fromthiophene and its bis-cyclized products, Molecules 16:523–531. https://doi.org/10.3390/molecules16010523
  • [4]. Khalil AM, Berghot MA and Gouda MA (2009) Synthesis and antibacterial activity of some newthiazole and thiophene derivatives, Eur. J. Med. Chem. 44:4434–4440 https://doi.org/10.1016/j.ejmech.2009.06.002
  • [5]. Rashad AE, Shamroukh AH, Abdel-Megeid RE, Mostafa A, El-Shesheny R, Kandeil A, Ali MA and Banert K (2010) Synthesis and screening of some novel fused thiophene and thienopyrimidine derivatives for anti-avian influenza virus (H5N1) activity, Eur. J. Med.Chem. 45:5251–5257. https://doi.org/10.1016/j.ejmech.2010.08.044
  • [6]. Forsch RA, Wright JE and Rosowsky A (2002) Synthesis and in vitro antitumor activity of thiopheneanalogues of 5-chloro-5,8-dideazafolic acid and 2-methyl-2-desamino-5-chloro- 5,8-dideazafolicacid, Bioorg. Med. Chem. 10:2067–2076 https://doi.org/10.1016/S0968-0896(02)00018-4
  • [7]. Saad HA, Youssef MM and Mosselhi MA (2011) Microwave assisted synthesis of some new fused1,2,4-triazines bearing thiophene moieties with expected pharmacological activity, Molecules, 16:4937–4957 https://doi.org/10.3390/molecules16064937
  • [8]. Aziz A, Salem AE, Sayed MA, Aboaly MM (2012). Synthesis, structural characterization, thermal studies, catalytic efficiency and antimicrobial activity of some M(II) complexes with ONO tridentate Schiff base N-salicylidene-o-aminophenol (saphH2). Journal of Molecular Structure, 1010:130-138. https://doi.org/10.1016/j.molstruc.2011.11.043
  • [9]. Sujarani A and Ramu A (2013) Synthesis, characterization, antimicrobial and DNA interaction studies of benzophenone - ethanamine schiff base with transition metal (II) [Cu(II), Co(II), Mn(II) and Ni(II)] complexes. Journal of Chemical and Pharmaceutical Research 5(4):347-358
  • [10]. Lam PL, Lee KKH, Kok SHL, Gambari R, Lam KH, Ho CL, Ma X, Lo YH, Wong WY, Dong QC, Bian ZX, Chui CH (2016), Antifungal study of substituted 4- pyridylmethylene-4’-aniline Schiff bases, RSC Adv., 106:104575-104581. https://doi.org/10.1039/C6RA20186E
  • [11]. Chopde HN, Meshram JS, Pandhurnekar CP, Pagadala R, Jonnalagadda SB (2016) Efficient Synthesis, Characterization, In Vitro Antibacterial and Antifungal Activity Study and Computational Tool for Prediction of Molecular Properties of Some Novel Schiff's Base via Betti's Protocol and Azetidinones,Journal of Heterocyclic Chemistry, 53(3):824-831. https://doi.org/10.1002/jhet.2349.
  • [12]. Kgokong JL, Smith PP, Matsabisa GM. (2005) 1,2,4-Triazino-[5,6b]indole derivatives: effects of the trifluoromethyl group on in vitro antimalarial activity. Bioorg Med Chem. Apr 15;13(8):2935-42. https://doi.org/10.1016/j.bmc.2005.02.017
  • [13]. Rathelot P, Vanelle P, Gasquet M, Delmas F, Crozet MP, Timon-David P, Maldonado J (1995) Synthesis of novel functionalized 5-nitroisoquinolines and evaluation of in vitro antimalarial activity, European Journal of Medicinal Chemistry, 30(6):503-508. https://doi.org/10.1016/0223-5234(96)88261-4
  • [14]. Kumar G, Devi S, Kumar D (2016) Synthesis of Schiff base 24-membered trivalent transition metal derivatives with their anti-inflammation and antimicrobial evaluation, J. Mole. Str., 1108:680-688. https://doi.org/10.1016/j.molstruc.2015.12.059
  • [15]. Alam MS, Choi JH, Lee DU. (2012) Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity. Bioorg Med Chem. 20(13):4103-8. https://doi.org/10.1016/j.bmc.2012.04.058
  • [16]. Jarrahpour A, Khalili D, De Clercq E, Salmi C, Brunel JM. (2007) Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-Schiff bases of isatin and their derivatives. Molecules. 12(8):1720-30. https://doi.org/10.3390/12081720
  • [17]. Nayab S, Alam A, Ahmad N, Khan SW, Khan W, Shams DF, Shah MIA, Ateeq M, Shah SK, and Hyosun Lee. (2023) Thiophene-Derived Schiff Base Complexes: Synthesis, Characterization, Antimicrobial Properties, and Molecular Docking. ACS Omega, 8 (20):17620-17633 https://doi.org/10.1021/acsomega.2c01981
  • [18]. Bingöl M, Turan N (2020) Schiff base and metal(II) complexes containing thiophene-3-carboxylate: Synthesis, characterization and antioxidant activities. Journal of Molecular Structure 1205(5):127542. https://doi.org/10.1016/j.molstruc.2019.127542
  • [19]. Unver Y, Unlüer D, Direkel S, Durdaği S. (2020) Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies. Turk J Chem. 44(4):1164-1176. https://doi.org/10.3906/kim-2004-78
  • [20]. Puthran D, Poojary B, Nayak SG, Purushotham N, Bhat M, Hedge H (2020) Novel Schiff bases–based thiophenes: Design, synthesisand biological evaluation. J Chin Chem Soc. 67:1278–1288. https://doi.org/10.1002/jccs.201900388
  • [21]. Langerman et al. (2020) Recent Advances in Acetylcholinesterase Inhibitors and Their Potential Applications in Central Nervous System Disorders. ACS Chemical Neuroscience 11(13): 1825-1836. https://doi.org/10.1021/acschemneuro.0c00029
  • [22]. Supuran CT (2010). Carbonic anhydrase inhibitors. Bioorganic & Medicinal Chemistry Letters, 20(12): 3467-3474. https://doi.org/10.1016/j.bmcl.2010.05.009
  • [23]. Zverova M. (2018) Alzheimer’s disease and blood-based biomarkers–potential contexts of use. Neuropsychiatric disease and treatment. 14:1877-1882. https://doi.org/10.2147/NDT.S172285
  • [24]. Zverova M. (2019) Clinical aspects of Alzheimer's disease. Clinical biochemistry. 72:3-6 https://doi.org/10.1016/j.clinbiochem.2019.04.015
  • [25]. Rezazadeh et al. (2020) A Review of Acetylcholinesterase Inhibitors as Alzheimer’s Disease Therapeutics. Neurotherapeutics 17(1): 53-77. https://doi.org/10.1007/s13311-019-00781-6
  • [26]. Sun MK and Alkon DL (2002) Carbonic anhydrase gating of attention: memory therapy and enhancement Trends Pharmacol. Sci., 23, 83-89. https://doi.org/10.1016/S0165-6147(02)01899-0
  • [27]. Lemon N, Canepa E, Ilies MA, Fossati S. (2021) Carbonic Anhydrases as Potential Targets Against Neurovascular Unit Dysfunction in Alzheimer's Disease and Stroke. Front Aging Neurosci. 13:772278. https://doi.org/10.3389/fnagi.2021.772278
  • [28]. Kidwai M, Negı N, Gupta S.D. (1994) Synthesis and antifertility activity of 1,5- diaryl-3(3’indolyl) formazans. Chem Pharm Bull (Tokyo) 42(11): 2363-64. https://doi.org/10.1248/cpb.42.2363
  • [29]. Xiang F, Xiang J, Fang Y, Zhang M, Li M. (2014) Discovering isozyme-selective inhibitor scaffolds of human carbonic anhydrases using structural alignment and de novo drug design approaches. Chem Biol Drug Des. 83(2):247-58. https://doi.org/10.1111/cbdd.12234
  • [30]. Gao H, Jiang Y, Zhan J, Sun Y. (2021) Pharmacophore-based drug design of AChE and BChE dual inhibitors as potential anti-Alzheimer's disease agents. Bioorg Chem.114:105149. https://doi.org/10.1016/j.bioorg.2021.105149
  • [31]. Huey R and Morris GM. (2008) Using AutoDock 4 with AutoDocktools: a tutorial. The Scripps Research Institute, USA. 54-56.
  • [32]. Trott O, Olson AJ. (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem. 31(2): 455-461. https://doi.org/10.1002/jcc.21334
  • [33]. Lill MA, Danielson ML. (2011) Computer-aided drug design platform using PyMOL. J Comput Aided Mol Des. 25(1): 13-19. https://doi.org/10.1007/s10822-010-9395-8
  • [34]. Biovia DS. (2017) Discovery studio visualizer. San Diego, CA, USA. 936.
  • [35]. Ellman GL, Courtney KD, Andres V, Featherstone RM (1961) A new and rapid colorimetric determination of acetylcholinesterase activity, Biochemical Pharmacology, 7(2): 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
  • [36]. Gocer H, Akıncıoğlu A, Oztaşkın N, Göksu S, Gulcin I (2013) Synthesis, antioxidant and antiacetylcholinesterase activities of sulfonamide derivatives of dopamine related compounds. Arch Pharm 346(11): 783–792. https://doi.org/10.1002/ardp.201300228
  • [37]. Bayram E, Senturk M, Kufrevioglu OI, Supuran CT (2008) In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II. Bioorg. Med. Chem., 6, 9101-9105. https://doi.org/10.1016/j.bmc.2008.09.028
  • [38]. Burmaoğlu S, Dilek E, Yılmaz AO, Supuran CT (2016) Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: an in vitro study. J. Enzyme Inhib. Med. Chem., 31(sup2):208-212. https://doi.org/10.1080/14756366.2016.1181626
  • [39]. Caglar S, Dilek E, Caglar B, Adigüzel E, Temel E, Buyukgungor O (2016) New metal complexes with diclofenac containing 2-pyridineethanol or 2-pyridinepropanol: synthesis, structural, spectroscopic, thermalproperties, catechol oxidase and carbonic anhydrase activities. J. Coord. Chem., 69:3321-3335. https://doi.org/10.1080/00958972.2016.1227802
  • [40]. Shirinzadeh H and Dilek E (2020) Synthesis, characterization and biological activity evaluation of novel naphthalenylmethylen hydrazine derivatives as carbonic anhydrase inhibitors. J. Mol. Struct., 1220: Article 128657. https://doi.org/10.1016/j.molstruc.2020.128657
  • [41]. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72:248-254. https://doi.org/10.1016/0003-2697(76)90527-3
  • [42]. Verpoorte J, Mehta S, Edsall JT (1967) Esterase activities of human carbonic anhydrases B and C. J. Biol. Chem. 242(18), 4221-4229. https://doi.org/10.1016/S0021-9258(18)95800-X
  • [43]. Redshaw C (2017) Use of Metal Catalysts Bearing Schiff Base Macrocycles for the Ring Opening Polymerization (ROP) of Cyclic Esters, Catalysts, 7(5): 165-176. https://doi.org/10.3390/catal7050165
  • [44]. DiRisio RJ, Armstrong JE, Frank MA, Lake WR, McNamara WR (2017) Cobalt Schiff-base complexes for electrocatalytic hydrogen generation, Dalton Trans., 46: 10418- 10425. https://doi.org/10.1039/C7DT01750B
  • [45]. Upadhyay KK, Kumar A, Upadhyay S, Mishra PC (2008) Synthesis, characterization, structural optimization using density functional theory and superoxide ion scavenging activity of some Schiff bases, J. Mol. Struct., 873: 5-16. https://doi.org/10.1016/j.molstruc.2007.02.031
  • [46]. Roberts DW, Schultz TW, Api AM, (2017) Skin Sensitization QMM for HRIPT NOEL Data: Aldehyde Schiff-Base Domain, Chem. Res. Toxicol., 30(6): 1309- 1316. https://doi.org/10.1021/acs.chemrestox.7b00050
  • [47]. Shokrollahi S, Amiri A, Fadaei-Tirani F, Schank-Job K (2020) Promising anti-cancer potency of 4,5,6,7-tetrahydrobenzo[d]thiazole-based Schiff-bases J. Mol. Liq. 2020, 300:122262. https://doi.org/10.1016/j.molliq.2019.112262
  • [48]. Shukla , Singh AP, Sonar P, Mishra M, Saraf K. (2016). Schiff bases of benzothiazol-2-ylamine and thiazolo[5,4-b] pyridin-2-ylamine as anticonvulsants: synthesis, characterization and toxicity profiling. Cent. Nerv. Syst. Agents Med. Chem. 16(3):240–248. DOI: 10.2174/1871524916666160428110728
  • [49]. Zoubi WA (2013) Biological Activities of Schiff Bases and Their Complexes: A Review of Recent Works. Int. J. Org. Chem., 3:73-95. DOI: 10.4236/ijoc.2013.33A008
Toplam 49 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Eczacılık Biyokimyası, Farmasotik Kimya, Toksikoloji
Bölüm Makaleler
Yazarlar

Şule Gürsoy 0000-0001-5236-5974

Zeynep Çaka 0009-0006-4061-7816

Nagihan Faydalı 0000-0002-8895-1825

Hanif Sirinzade 0000-0001-9663-9199

Esra Dilek 0000-0002-3629-5168

Proje Numarası 1919B012109379
Erken Görünüm Tarihi 27 Mart 2024
Yayımlanma Tarihi 28 Mart 2024
Gönderilme Tarihi 17 Ekim 2023
Kabul Tarihi 7 Mart 2024
Yayımlandığı Sayı Yıl 2024 Cilt: 17 Sayı: 1

Kaynak Göster

APA Gürsoy, Ş., Çaka, Z., Faydalı, N., Sirinzade, H., vd. (2024). Exploring Novel Schiff Base Compounds Derived from Benzothiophene-3- carboxaldehyde Hydrazones: In vitro and In silico Evaluation as Potential Inhibitors of Cholinesterases and Carbonic Anhydrases I-II. Erzincan University Journal of Science and Technology, 17(1), 174-195. https://doi.org/10.18185/erzifbed.1377310
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