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Article

Biological Evaluation, Molecular Docking, and SAR Studies of Novel 2-(2,4-Dihydroxyphenyl)-1H- Benzimidazole Analogues

by
Joanna Matysiak
1,*,
Alicja Skrzypek
1,
Monika Karpińska
2,
Kamila Czarnecka
3,
Paweł Szymański
3,
Marek Bajda
4 and
Andrzej Niewiadomy
1,2
1
Department of Chemistry, University of Life Sciences in Lublin, Akademicka 15, 20-950 Lublin, Poland
2
Łukasiewicz Research Network – Institute of Industrial Organic Chemistry, Annopol 6, 03-236 Warsaw, Poland
3
Department of Pharmaceutical Chemistry, Drug Analyses and Radiopharmacy, Faculty of Pharmacy, Medical University of Lodz, Muszynskiego 1, 90-151 Lodz, Poland
4
Department of Physicochemical Drug Analysis, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Cracow, Poland
*
Author to whom correspondence should be addressed.
Biomolecules 2019, 9(12), 870; https://doi.org/10.3390/biom9120870
Submission received: 11 November 2019 / Revised: 9 December 2019 / Accepted: 10 December 2019 / Published: 12 December 2019
(This article belongs to the Special Issue Advances in Cholinesterases)
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Abstract

In the present study, new 4-(1H-benzimidazol-2-yl)-benzene-1,3-diols, modified in both rings, have been synthesized and their efficacies as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors have been determined. The modified Ellman’s spectrophotometric method was applied for the biological evaluation. The compounds showed strong (IC50 80–90 nM) AChE and moderate (IC50 5–0.2 µM) BuChE inhibition in vitro. Some compounds were effective toward AChE/BuChE, exhibiting high selectivity ratios versus BuChE, while the other compounds were active against both enzymes. The structure–activity relationships were discussed. The compounds inhibited also in vitro self-induced Aβ(1–42) aggregation and exhibited antioxidant properties. The docking simulations showed that the benzimidazoles under consideration interact mainly with the catalytic site of AChE and mimic the binding mode of tacrine.
Keywords: benzimidazole; acetylcholinesterase; butyrylcholinesterase; inhibitor; beta amyloid; molecular docking; lipophilicity; SAR benzimidazole; acetylcholinesterase; butyrylcholinesterase; inhibitor; beta amyloid; molecular docking; lipophilicity; SAR

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MDPI and ACS Style

Matysiak, J.; Skrzypek, A.; Karpińska, M.; Czarnecka, K.; Szymański, P.; Bajda, M.; Niewiadomy, A. Biological Evaluation, Molecular Docking, and SAR Studies of Novel 2-(2,4-Dihydroxyphenyl)-1H- Benzimidazole Analogues. Biomolecules 2019, 9, 870. https://doi.org/10.3390/biom9120870

AMA Style

Matysiak J, Skrzypek A, Karpińska M, Czarnecka K, Szymański P, Bajda M, Niewiadomy A. Biological Evaluation, Molecular Docking, and SAR Studies of Novel 2-(2,4-Dihydroxyphenyl)-1H- Benzimidazole Analogues. Biomolecules. 2019; 9(12):870. https://doi.org/10.3390/biom9120870

Chicago/Turabian Style

Matysiak, Joanna, Alicja Skrzypek, Monika Karpińska, Kamila Czarnecka, Paweł Szymański, Marek Bajda, and Andrzej Niewiadomy. 2019. "Biological Evaluation, Molecular Docking, and SAR Studies of Novel 2-(2,4-Dihydroxyphenyl)-1H- Benzimidazole Analogues" Biomolecules 9, no. 12: 870. https://doi.org/10.3390/biom9120870

APA Style

Matysiak, J., Skrzypek, A., Karpińska, M., Czarnecka, K., Szymański, P., Bajda, M., & Niewiadomy, A. (2019). Biological Evaluation, Molecular Docking, and SAR Studies of Novel 2-(2,4-Dihydroxyphenyl)-1H- Benzimidazole Analogues. Biomolecules, 9(12), 870. https://doi.org/10.3390/biom9120870

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