Two dimensional-QSAR and molecular dynamics studies of a selected class of aldoxime- and hydroxy-functionalized chalcones as monoamine oxidase-B inhibitors

References

• Abdelgawad, M. A., Oh, J. M., Parambi, D. G., Kumar, S., Musa, A., Ghoneim, M. M., Nayl, A. A., El-Ghorab, A. H., Ahmad, I., Patel, H., Kim, H., & Mathew, B. (2022). Development of bromo-and fluoro-based α, β-unsaturated ketones as highly potent MAO-B inhibitors for the treatment of Parkinson’s disease. Journal of Molecular Structure, 1266, 133545. https://doi.org/10.1016/j.molstruc.2022.133545
   Web of Science ®Google Scholar
• Ambure, P., Bhat, J., Puzyn, T., & Roy, K. (2019). Identifying natural compounds as multi-target-directed ligands against Alzheimer’s disease: An in silico approach. Journal of Biomolecular Structure & Dynamics, 37(5), 1282–1306. https://doi.org/10.1080/07391102.2018.1456975
   PubMed Web of Science ®Google Scholar
• Bharadwaj, K. K., Ahmad, I., Pati, S., Ghosh, A., Sarkar, T., Rabha, B., Patel, H., Baishya, D., Edinur, H. A., Abdul Kari, Z., Ahmad Mohd Zain, M. R., & Wan Rosli, W. I. (2022). Potent bioactive compounds from seaweed waste to combat cancer through bioinformatics investigation. Frontiers in Nutrition, 9, 889276. https://doi.org/10.3389/fnut.2022.889276
   PubMed Web of Science ®Google Scholar
• Binda, C., Wang, J., Pisani, L., Caccia, C., Carotti, A., Salvati, P., Edmondson, D. E., & Mattevi, A. (2007). Structures of human monoamine oxidase B complexes with selective noncovalent inhibitors: Safinamide and coumarin analogs. Journal of Medicinal Chemistry, 50(23), 5848–5852. https://doi.org/10.1021/jm070677y
   PubMed Web of Science ®Google Scholar
• Boulaamane, Y., Ahmad, I., Patel, H., Das, N., Britel, M. R., & Maurady, A. (2022). Structural exploration of selected C6 and C7-substituted coumarin isomers as selective MAO-B inhibitors. Journal of Biomolecular Structure and Dynamics, 1–15. https://doi.org/10.1080/07391102.2022.2033643
   PubMed Web of Science ®Google Scholar
• Carradori, S., Secci, D., & Petzer, J. P. (2018). MAO inhibitors and their wider applications: A patent review. Expert Opinion on Therapeutic Patents, 28(3), 211–226. https://doi.org/10.1080/13543776.2018.1427735
   PubMed Web of Science ®Google Scholar
• Gramatica, P., Chirico, N., Papa, E., Cassani, S., & Kovarich, S. (2013). QSARINS: A new software for the development, analysis, and validation of QSAR MLR models. Journal of Computational Chemistry, 34(24), 2121–2132. https://doi.org/10.1002/jcc.23361
   Web of Science ®Google Scholar
• Guglielmi, P., Carradori, S., Ammazzalorso, A., & Secci, D. (2019). Novel approaches to the discovery of selective human monoamine oxidase-B inhibitors: Is there room for improvement? Expert Opinion on Drug Discovery, 14(10), 995–1035. https://doi.org/10.1080/17460441.2019.1637415
   PubMed Web of Science ®Google Scholar
• Guglielmi, P., Carradori, S., D'Agostino, I., Campestre, C., & Petzer, J. P. (2022). An updated patent review on monoamine oxidase (MAO) inhibitors. Expert Opinion on Therapeutic Patent, 32(8), 849-883. https://doi.org/10.1080/13543776.2022.2083501
   PubMed Web of Science ®Google Scholar
• Guglielmi, P., Mathew, B., Secci, D., & Carradori, S. (2020). Chalcones: Unearthing their therapeutic possibility as monoamine oxidase B inhibitors. European Journal of Medicinal Chemistry, 205, 112650. https://doi.org/10.1016/j.ejmech.2020.112650
   PubMed Web of Science ®Google Scholar
• Harilal, S., Kumar, R., Mathew, G. E., Jose, J., Uddin, M. S., & Mathew, B. (2020). Neurochemicals in nervous system and exploring the chemical make-up of human brain. In B. Mathew, & D.G. Thomas Parambi (Eds.), Principles of neurochemistry. Springer.
   Google Scholar
• Hong, R., & Li, X. (2018). Discovery of monoamine oxidase inhibitors by medicinal chemistry approaches. MedChemComm, 10(1), 10–25. https://doi.org/10.1039/c8md00446c
   PubMed Web of Science ®Google Scholar
• Iacovino, L. G., Pinzi, L., Facchetti, G., Bortolini, B., Christodoulou, M. S., Binda, C., Rastelli, G., Rimoldi, I., Passarella, D., Di Paolo, M. L., & Dalla Via, L. (2021). Promising non-cytotoxic monosubstituted chalcones to target monoamine oxidase-B. ACS Medicinal Chemistry Letters, 12(7), 1151–1158. https://doi.org/10.1021/acsmedchemlett.1c00238
   PubMed Web of Science ®Google Scholar
• Is, Y. S., Aksoydan, B., Senturk, M., Yurtsever, M., & Durdagi, S. (2020). Integrated binary QSAR-driven virtual screening and in vitro studies for finding novel hMAO-B-selective inhibitors. Journal of Chemical Information and Modeling, 60(8), 4047–4055. https://doi.org/10.1021/acs.jcim.0c00169
   PubMed Web of Science ®Google Scholar
• Koyiparambath, V. P., Prayaga Rajappan, K., Rangarajan, T. M., Al-Sehemi, A. G., Pannipara, M., Bhaskar, V., Nair, A. S., Sudevan, S. T., Kumar, S., & Mathew, B. (2021). Deciphering the detailed structure-activity relationship of coumarins as Monoamine oxidase enzyme inhibitors—An updated review. Chemical Biology & Drug Design, 98(4), 655–673. https://doi.org/10.1111/cbdd.13919
   PubMed Web of Science ®Google Scholar
• Kumar, S., Nair, A. S., Abdelgawad, M. A., & Mathew, B. (2022). Exploration of the detailed structure-activity relationships of isatin and their isomers as monoamine oxidase inhibitors. ACS Omega, 7(19), 16244–16259. https://doi.org/10.1021/acsomega.2c01470
   PubMed Web of Science ®Google Scholar
• Mathew, B., Adeniyi, A. A., Dev, S., Joy, M., Ucar, G., Mathew, G. E., Singh-Pillay, A., & Soliman, M. E. (2017). Pharmacophore-based 3D-QSAR analysis of thienyl chalcones as a new class of human MAO-B inhibitors: Investigation of combined quantum chemical and molecular dynamics approach. The Journal of Physical Chemistry. B, 121(6), 1186–1203. https://doi.org/10.1021/acs.jpcb.6b09451
   PubMed Web of Science ®Google Scholar
• Mathew, B., & Kim, H. (2020). Inhibitors of monoamine oxidase and acetylcholinesterase as a front runner in CNS drug discovery. Combinatorial Chemistry & High Throughput Screening, 23(9), 834–835. https://doi.org/10.2174/138620732309201127093123
   PubMed Web of Science ®Google Scholar
• Mathew, B., Mathew, G. E., Petzer, J. P., & Petzer, A. (2017a). Structural exploration of synthetic chromones as selective MAO-B inhibitors: A mini review. Combinatorial Chemistry & High Throughput Screening, 20(6), 522–532.
   PubMed Web of Science ®Google Scholar
• Mellado, M., González, C., Mella, J., Aguilar, L. F., Viña, D., Uriarte, E., Cuellar, M., & Matos, M. J. (2021). Combined 3D-QSAR and docking analysis for the design and synthesis of chalcones as potent and selective monoamine oxidase B inhibitors. Bioorganic Chemistry, 108, 104689. https://doi.org/10.1016/j.bioorg.2021.104689
   PubMed Web of Science ®Google Scholar
• Oh, J. M., Rangarajan, T. M., Chaudhary, R., Gambacorta, N., Nicolotti, O., Kumar, S., Mathew, B., & Kim, H. (2022). Aldoxime-and hydroxy-functionalized chalcones as highly potent and selective monoamine oxidase-B inhibitors. Journal of Molecular Structure, 1250, 131817. https://doi.org/10.1016/j.molstruc.2021.131817
   Web of Science ®Google Scholar
• Ramesh, M., & Muthuraman, A. (2020). Quantitative Structure-Activity Relationship (QSAR) studies for the inhibition of MAOs. Combinatorial Chemistry & High Throughput Screening, 23(9), 887–897. https://doi.org/10.2174/1386207323666200324173231
   PubMed Web of Science ®Google Scholar
• Ramsay, R. R. (2016). Molecular aspects of monoamine oxidase B. Progress in Neuro-Psychopharmacology & Biological Psychiatry, 69, 81–89. https://doi.org/10.1016/j.pnpbp.2016.02.005
   PubMed Web of Science ®Google Scholar
• Rangarajan, T. M., Kaushik, K., Singh, R. P., Singh, M., Singh., & R. P., Reeta. (2020). Efficient solvent- and temperature-tuned access to aldoxime ethers and phenolic func- tions by Pd-catalyzed C–O cross-coupling of aldoximes with aryl bromides and bromo-chalcones. New Journal of Chemistry, 44, 1326–1336. https://doi.org/10.1039/C9NJ05124D
   Web of Science ®Google Scholar
• Rangarajan, T. M., & Mathew, B. (2021). Updates on pyrazolines derivatives as promising scaffold for neuropsychiatric and neurodegenerative disorders. Current Topics in Medicinal Chemistry, 21(30), 2695–2714. https://doi.org/10.2174/1568026621999210902123132
   PubMed Web of Science ®Google Scholar
• Rehuman, N. A., Oh, J. M., Nath, L. R., Khames, A., Abdelgawad, M. A., Gambacorta, N., Nicolotti, O., Jat, R. K., Kim, H., & Mathew, B. (2021). Halogenated coumarin-chalcones as multifunctional monoamine oxidase-B and butyrylcholinesterase inhibitors. ACS Omega, 6(42), 28182–28193. https://doi.org/10.1021/acsomega.1c04252
   PubMed Web of Science ®Google Scholar
• Riederer, P., & Müller, T. (2017). Use of monoamine oxidase inhibitors in chronic neurodegeneration. Expert Opinion on Drug Metabolism & Toxicology, 13(2), 233–240. https://doi.org/10.1080/17425255.2017.1273901
   PubMed Web of Science ®Google Scholar
• Shaw, D. E. (2021). Desmond molecular dynamics system. Maestro-Desmond interoperability tools. Research, Schrödinger Release.
   Google Scholar
• Son, S. Y., Ma, J., Kondou, Y., Yoshimura, M., Yamashita, E., & Tsukihara, T. (2008). Structure of human monoamine oxidase A at 2.2-A resolution: The control of opening the entry for substrates/inhibitors. Proceedings of the National Academy of Sciences of the United States of America, 105(15), 5739–5744. https://doi.org/10.1073/pnas.0710626105
   PubMed Web of Science ®Google Scholar
• Szatmari, B., Balicza, P., Nemeth, G., & Molnar, M. J. (2019). The panomics approach in neurodegenerative disorders. Current Medicinal Chemistry, 26(10), 1712–1720. https://doi.org/10.2174/0929867324666170705120038
   PubMed Web of Science ®Google Scholar
• Tripathi, R. K. P., & Ayyannan, S. R. (2019). Monoamine oxidase-B inhibitors as potential neurotherapeutic agents: An overview and update. Medicinal Research Reviews, 39(5), 1603–1706. https://doi.org/10.1002/med.21561
   PubMed Web of Science ®Google Scholar
• Veerasamy, R., Rajak, H., Jain, A., Sivadasan, S., Varghese, C. P., & Agrawal, R. K. (2011). Validation of QSAR models-strategies and importance. International Journal of Drug Design and Discovery, 3, 511–519.
   Google Scholar