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Volume 25
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Article

Novel Class of Chalcone Oxime Ethers as Potent Monoamine Oxidase-B and Acetylcholinesterase Inhibitors

by
Jong Min Oh
1,
T. M. Rangarajan
2,*,
Reeta Chaudhary
3,4,
Rishi Pal Singh
2,
Manjula Singh
5,
Raj Pal Singh
3,
Anna Rita Tondo
6,
Nicola Gambacorta
6,
Orazio Nicolotti
6,
Bijo Mathew
7,* and
Hoon Kim
1,*
1
Department of Pharmacy, and Research Institute of Life Pharmaceutical Sciences, Sunchon National University, Suncheon 57922, Korea
2
Department of Chemistry, Sri Venketeswara College, University of Delhi, New Delhi-110021, India
3
Centre for Fire, Explosive and Environment Saftey, DRDO, Delhi-110054, India
4
Department of Chemistry, University of Dehli, Dehli-110007, India
5
Department of Chemistry, Shivaji College, University of Delhi, New Delhi-110027, India
6
Dipartimento di Farmacia—Scienze del Farmaco, Università degli Studi di Bari “Aldo Moro”, via E. Orabona, 4, I-70125 Bari, Italy
7
Division of Drug Design and Medicinal Chemistry Research Lab, Department of Pharmaceutical Chemistry, Ahalia School of Pharmacy, Palakkad-678557, Kerala, India
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(10), 2356; https://doi.org/10.3390/molecules25102356
Received: 24 April 2020 / Revised: 13 May 2020 / Accepted: 13 May 2020 / Published: 18 May 2020
(This article belongs to the Special Issue Multifunctional Hybrid and Chimeric Compounds as Candidates for the Treatment of Neurological and Neurodegenerative Disorders)
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Abstract

Previously synthesized novel chalcone oxime ethers (COEs) were evaluated for inhibitory activities against monoamine oxidases (MAOs) and acetylcholinesterase (AChE). Twenty-two of the 24 COEs synthesized, except COE-17 and COE-24, had potent and/or significant selective inhibitory effects on MAO-B. COE-6 potently inhibited MAO-B with an IC50 value of 0.018 µM, which was 105, 2.3, and 1.1 times more potent than clorgyline, lazabemide, and pargyline (reference drugs), respectively. COE-7, and COE-22 were also active against MAO-B, both had an IC50 value of 0.028 µM, which was 67 and 1.5 times lower than those of clorgyline and lazabemide, respectively. Most of the COEs exhibited weak inhibitory effects on MAO-A and AChE. COE-13 most potently inhibited MAO-A (IC50 = 0.88 µM) and also significantly inhibited MAO-B (IC50 = 0.13 µM), and it could be considered as a potential nonselective MAO inhibitor. COE-19 and COE-22 inhibited AChE with IC50 values of 5.35 and 4.39 µM, respectively. The selectivity index (SI) of COE-22 for MAO-B was higher than that of COE-6 (SI = 778.6 vs. 222.2), but the IC50 value (0.028 µM) was slightly lower than that of COE-6 (0.018 µM). In reversibility experiments, inhibitions of MAO-B by COE-6 and COE-22 were recovered to the levels of reference reversible inhibitors and both competitively inhibited MAO-B, with Ki values of 0.0075 and 0.010 µM, respectively. Our results show that COE-6 and COE-22 are potent, selective MAO-B inhibitors, and COE-22 is a candidate of dual-targeting molecule for MAO-B and AChE. View Full-Text
Keywords: monoamine oxidase; acetylcholinesterase; chalcones; oximes; kinetics; reversibility monoamine oxidase; acetylcholinesterase; chalcones; oximes; kinetics; reversibility
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
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MDPI and ACS Style

Oh, J.M.; Rangarajan, T.M.; Chaudhary, R.; Singh, R.P.; Singh, M.; Singh, R.P.; Tondo, A.R.; Gambacorta, N.; Nicolotti, O.; Mathew, B.; Kim, H. Novel Class of Chalcone Oxime Ethers as Potent Monoamine Oxidase-B and Acetylcholinesterase Inhibitors. Molecules 2020, 25, 2356. https://doi.org/10.3390/molecules25102356

AMA Style

Oh JM, Rangarajan TM, Chaudhary R, Singh RP, Singh M, Singh RP, Tondo AR, Gambacorta N, Nicolotti O, Mathew B, Kim H. Novel Class of Chalcone Oxime Ethers as Potent Monoamine Oxidase-B and Acetylcholinesterase Inhibitors. Molecules. 2020; 25(10):2356. https://doi.org/10.3390/molecules25102356

Chicago/Turabian Style

Oh, Jong M., T. M. Rangarajan, Reeta Chaudhary, Rishi P. Singh, Manjula Singh, Raj P. Singh, Anna R. Tondo, Nicola Gambacorta, Orazio Nicolotti, Bijo Mathew, and Hoon Kim. 2020. "Novel Class of Chalcone Oxime Ethers as Potent Monoamine Oxidase-B and Acetylcholinesterase Inhibitors" Molecules 25, no. 10: 2356. https://doi.org/10.3390/molecules25102356

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