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Research Articles

Structural exploration of selected C6 and C7-substituted coumarin isomers as selective MAO-B inhibitors

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Pages 2326-2340 | Received 12 Aug 2021, Accepted 10 Jan 2022, Published online: 15 Feb 2022

References

  • Ahmad, I., Jadhav, H., Shinde, Y., Jagtap, V., Girase, R., & Patel, H. (2021). Optimizing Bedaquiline for cardiotoxicity by structure based virtual screening, DFT analysis and molecular dynamic simulation studies to identify selective MDR-TB inhibitors. In Silico Pharmacology, 9(1), 23. https://doi.org/10.1007/s40203-021-00086-x
  • Binda, C., Li, M., Hubálek, F., Restelli, N., Edmondson, D. E., & Mattevi, A. (2003). Insights into the mode of inhibition of human mitochondrial monoamine oxidase B from high-resolution crystal structures. Proceedings of the National Academy of Sciences, 100(17), 9750–9755. https://doi.org/10.1073/pnas.1633804100
  • Binda, C., Mattevi, A., & Edmondson, D. E. (2011). Structural properties of human monoamine oxidases A and B. International Review of Neurobiology, 100, 1–11.
  • Binda, C., Newton-Vinson, P., Hubálek, F., Edmondson, D. E., & Mattevi, A. (2002). Structure of human monoamine oxidase B, a drug target for the treatment of neurological disorders. Nature Structural Biology, 9(1), 22–26.
  • 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.
  • Congreve, M., Carr, R., Murray, C., & Jhoti, H. (2003). A'rule of three'for fragment-based lead discovery? Drug Discovery Today, 8(19), 876–877.
  • Culpepper, L. (2013). Reducing the burden of difficult-to-treat major depressive disorder: Revisiting monoamine oxidase inhibitor therapy. The Primary Care Companion for CNS Disorders, 15(5), 27220. https://doi.org/10.4088/PCC.13r01515
  • D. E. Shaw Research, Schrödinger Release. (2020–3). Desmond molecular dynamics system. Maestro-Desmond interoperability tools.
  • Das, D., Koh, Y., Tojo, Y., Ghosh, A. K., & Mitsuya, H. (2009). Prediction of potency of protease inhibitors using free energy simulations with polarizable quantum mechanics-based ligand charges and a hybrid water model. Journal of Chemical Information and Modeling, 49(12), 2851–2862. https://doi.org/10.1021/ci900320p
  • De Colibus, L., Li, M., Binda, C., Lustig, A., Edmondson, D. E., & Mattevi, A. (2005). Three- dimensional structure of human monoamine oxidase A (MAO A): Relation to the structures of rat MAO A and human MAO B. Proceedings of the National Academy of Sciences, 102(36), 12684–12689. https://doi.org/10.1073/pnas.0505975102
  • Dorsey, E. R., Elbaz, A., Nichols, E., Abbasi, N., Abd-Allah, F., Abdelalim, A., Adsuar, J. C., Ansha, M. G., Brayne, C., Choi, J.-Y J., Collado-Mateo, D., Dahodwala, N., Do, H. P., Edessa, D., Endres, M., Fereshtehnejad, S.-M., Foreman, K. J., Gankpe, F. G., Gupta, R., … Murray, C. J. L. (2018). Global, reginal, and national burden of Parkinson's disease, 199–2016: A systematic analysis for the Global Burden of Disease Study 2016. The Lancet Neurology, 17(11), 939–953. https://doi.org/10.1016/S1474-4422(18)30295-3
  • Edmondson, D. E., Binda, C., & Mattevi, A. (2007). Structural insights into the mechanism of amine oxidation by monoamine oxidases A and B. Archives of Biochemistry and Biophysics, 464(2), 269–276. https://doi.org/10.1016/j.abb.2007.05.006
  • Finberg, J. P., & Rabey, J. M. (2016). Inhibitors of MAO-A and MAO-B in psychiatry and neurology. Frontiers in Pharmacology, 7, 340.
  • Friesner, R. A., Banks, J. L., Murphy, R. B., Halgren, T. A., Klicic, J. J., Mainz, D. T., Repasky, M. P., Knoll, E. H., Shelley, M., Perry, J. K., Shaw, D. E., Francis, P., & Shenkin, P. S. (2004). Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. Journal of Medicinal Chemistry, 47(7), 1739–1749.
  • Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., & Mainz, D. T. (2006). Extra precision glide: Docking and scoring incorporating a model of hydrophobic enclosure for protein − ligand complexes. Journal of Medicinal Chemistry, 49(21), 6177–6196. https://doi.org/10.1021/jm051256o
  • Gaweska, H., & Fitzpatrick, P. F. (2011). Structures and mechanism of the monoamine oxidase family, 2(5), 365–377. https://doi.org/10.1515/BMC.2011.030
  • Genheden, S., & Ryde, U. (2015). The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities. Expert Opinion on Drug Discovery, 10(5), 449–461. https://doi.org/10.1517/17460441.2015.1032936
  • Greenwood, J. R., Calkins, D., Sullivan, A. P., & Shelley, J. C. (2010). Towards the comprehensive, rapid, and accurate prediction of the favorable tautomeric states of drug-like molecules in aqueous solution. Journal of Computer-Aided Molecular Design, 24(6–7), 591–604.
  • Halgren, T. A., Murphy, R. B., Friesner, R. A., Beard, H. S., Frye, L. L., Pollard, W. T., & Banks, J. L. (2004). Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. Journal of Medicinal Chemistry, 47(7), 1750–1759.
  • Jacobson, M. P., Friesner, R. A., Xiang, Z., & Honig, B. (2002). On the role of the crystal environment in determining protein side-chain conformations. Journal of Molecular Biology, 320(3), 597–608.
  • Jacobson, M. P., Pincus, D. L., Rapp, C. S., Day, T. J., Honig, B., Shaw, D. E., & Friesner, R. A. (2004). A hierarchical approach to all‐atom protein loop prediction. Proteins: Structure, Function, and Bioinformatics, 55(2), 351–367. https://doi.org/10.1002/prot.10613
  • Jorgensen, W. L., Maxwell, D. S., & Tirado-Rives, J. (1996). Development and testing of the OPLS all atom force field on conformational energetics and properties of organic liquids. Journal of the American Chemical Society, 118(45), 11225–11236. https://doi.org/10.1021/ja9621760
  • Knez, D., Colettis, N., Iacovino, L. G., Sova, M., Pišlar, A., Konc, J., Lešnik, S., Higgs, J., Kamecki, F., Mangialavori, I., Dolšak, A., Žakelj, S., Trontelj, J., Kos, J., Binda, C., Marder, M., & Gobec, S. (2020). Stereoselective activity of 1-propargyl-4-styrylpiperidine-like analogues that can discriminate between monoamine oxidase isoforms A and B. Journal of Medicinal Chemistry, 63(3), 1361–1387. https://doi.org/10.1021/acs.jmedchem.9b01886
  • Lee, H. Y., Cho, D. Y., Ahmad, I., Patel, H. M., Kim, M. J., Jung, J. G., Jeong, E. H., Haque, M. A., & Cho, K. M. (2021). Mining of a novel esterase (est3S) gene from a cow rumen metagenomic library with organosphosphorus insecticides degrading capability: Catalytic insights by site directed mutations, docking, and molecular dynamic simulations. International Journal of Biological Macromolecules, 190, 441–455.
  • Li, J., Abel, R., Zhu, K., Cao, Y., Zhao, S., & Friesner, R. A. (2011). The VSGB 2.0 model: A next generation energy model for high resolution protein structure modeling. Proteins: Structure, Function, and Bioinformatics, 79(10), 2794–2812. https://doi.org/10.1002/prot.23106
  • Lin, J., Sahakian, D. C., De Morais, S. M., Xu, J. J., Polzer, R. J., & Winter, S. M. (2003). The role of absorption, distribution, metabolism, excretion and toxicity in drug discovery. Current Topics in Medicinal Chemistry, 3(10), 1125–1154.
  • Lipinski, C. A. (2004). Lead- and drug-like compounds: The rule-of-five revolution . Drug Discovery Today. Technologies, 1(4), 337–341. https://doi.org/10.1016/j.ddtec.2004.11.007
  • Lyne, P. D., Lamb, M. L., & Saeh, J. C. (2006). Accurate prediction of the relative potencies of members of a series of kinase inhibitors using molecular docking and MM-GBSA scoring. Journal of Medicinal Chemistry, 49(16), 4805–4808.
  • Mallajosyula, J. K., Kaur, D., Chinta, S. J., Rajagopalan, S., Rane, A., Nicholls, D. G., Di Monte, D. A., MacArthur, H., & Andersen, J. K. (2008). MAO-B elevation in mouse brain astrocytes results in Parkinson's pathology. PLoS ONE, 3(2), e1616. https://doi.org/10.1371/journal.pone.0001616
  • Martyna, G. J. (1994). Remarks on "Constant-temperature molecular dynamics with momentum conservation". Physical Review. E, Statistical Physics, Plasmas, Fluids, and Related Interdisciplinary Topics, 50(4), 3234–3236. https://doi.org/10.1103/physreve.50.3234
  • Mehta, C. H., Narayan, R., Aithal, G., Pandiyan, S., Bhat, P., Dengale, S., Shah, A., Nayak, U. Y., & Garg, S. (2019). Molecular simulation driven experiment for formulation of fixed dose combination of Darunavir and Ritonavir as anti-HIV nanosuspension. Journal of Molecular Liquids, 293, 111469. https://doi.org/10.1016/j.molliq.2019.111469
  • Mertens, M. D., Hinz, S., Müller, C. E., & Gütschow, M. (2014). Alkynyl-coumarinyl ethers as MAO-B inhibitors. Bioorganic & Medicinal Chemistry, 22(6), 1916–1928. https://doi.org/10.1016/j.bmc.2014.01.046
  • Mostert, S., Petzer, A., & Petzer, J. P. (2015). Indanones as high‐potency reversible inhibitors of monoamine oxidase. ChemMedChem, 10(5), 862–873. https://doi.org/10.1002/cmdc.201500059
  • Noda, S., Sato, S., Fukuda, T., Tada, N., Uchiyama, Y., Tanaka, K., & Hattori, N. (2020). Loss of Parkin contributes to mitochondrial turnover and dopaminergic neuronal loss in aged mice. Neurobiology of Disease, 136, 104717. https://doi.org/10.1016/j.nbd.2019.104717
  • Olsson, M. H., Søndergaard, C. R., Rostkowski, M., & Jensen, J. H. (2011). PROPKA3: Consistent treatment of internal and surface residues in empirical p K a predictions. Journal of Chemical Theory and Computation, 7(2), 525–537. https://doi.org/10.1021/ct100578z
  • Pawara, R., Ahmad, I., Surana, S., & Patel, H. (2021). Computational identification of 2,4-disubstituted amino-pyrimidines as L858R/T790M-EGFR double mutant inhibitors using pharmacophore mapping, molecular docking, binding free energy calculation, DFT study and molecular dynamic simulation. In Silico Pharmacol, 9 (1), 54. https://doi.org/10.1007/s40203-021-00113-x
  • Poewe, W., & Mahlknecht, P. (2020). Pharmacologic treatment of motor symptoms associated with Parkinson disease. Neurologic Clinics, 38(2), 255–267. https://doi.org/10.1016/j.ncl.2019.12.002
  • Rempel, V., Volz, N., Hinz, S., Karcz, T., Meliciani, I., Nieger, M., Wenzel, W., Bräse, S., & Müller, C. E. (2012). 7-Alkyl-3-benzylcoumarins: A versatile scaffold for the development of potent and selective cannabinoid receptor agonists and antagonists. Journal of Medicinal Chemistry, 55(18), 7967–7977.
  • Roos, K., Wu, C., Damm, W., Reboul, M., Stevenson, J. M., Lu, C., Dahlgren, M. K., Mondal, S., Chen, W., Wang, L., Abel, R., Friesner, R. A., & Harder, E. D. (2019). OPLS3e: Extending force field coverage for drug-like small molecules. Journal of Chemical Theory and Computation, 15(3), 1863–1874. https://doi.org/10.1021/acs.jctc.8b01026
  • Schrödinger Release: Maestro. (2021). Schrödinger, LLC.
  • Shih, J. C., Chen, K., & Ridd, M. J. (1999). Monoamine oxidase: From genes to behavior. Annual Review of Neuroscience, 22(1), 197–217.
  • Son, S. Y., Ma, J., Kondou, Y., Yoshimura, M., Yamashita, E., & Tsukihara, T. (2008). Structure of human monoamine oxidase A at 2.2-Å resolution: The control of opening the entry for substrates/inhibitors. Proceedings of the National Academy of Sciences, 105(15), 5739–5744. https://doi.org/10.1073/pnas.0710626105
  • Tetrud, J. W., & Koller, W. C. (2004). A novel formulation of selegiline for the treatment of Parkinson’s disease. Neurology, 63(7 Suppl 2), S2–S6. suppl
  • Vora, J., Patel, S., Athar, M., Sinha, S., Chhabria, M. T., Jha, P. C., & Shrivastava, N. (2019). Pharmacophore modeling, molecular docking and molecular dynamics simulation for screening and identifying anti-dengue phytocompounds. Journal of Biomolecular Structure and Dynamics, 38(6), 1726–1740. https://doi.org/10.1080/07391102.2019.1615002
  • Wang, D., Hong, R. Y., Guo, M., Liu, Y., Chen, N., Li, X., & Kong, D. X. (2019). Novel C7-substituted coumarins as selective monoamine oxidase inhibitors: Discovery, synthesis and theoretical simulation. Molecules, 24(21), 4003. https://doi.org/10.3390/molecules24214003
  • Youdim, M. B., Gross, A., & Finberg, J. P. (2001). Rasagiline [N‐propargyl‐1R (+)‐aminoindan], a selective and potent inhibitor of mitochondrial monoamine oxidase B. British Journal of Pharmacology, 132(2), 500–506.
  • Youdim, M. B., Edmondson, D., & Tipton, K. F. (2006). The therapeutic potential of monoamine oxidase inhibitors. Nature Reviews. Neuroscience, 7(4), 295–309.
  • Zrieq, R., Ahmad, I., Snoussi, M., Noumi, E., Iriti, M., Algahtani, F. D., Patel, H., Saeed, M., Tasleem, M., Sulaiman, S., Aouadi, K., & Kadri, A. (2021). Tomatidine and Patchouli alcohol as inhibitors of SARS-CoV-2 enzymes (3CLpro, PLpro and NSP15) by molecular docking and molecular dynamics simulations. International Journal of Molecular Sciences, 22(19), 10693. https://doi.org/10.3390/ijms221910693

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