Development of methylthiosemicarbazones as new reversible monoamine oxidase-B inhibitors for the treatment of Parkinson’s disease

References

• Angelopoulou, E., Pyrgeli, E. S., & Piperi, C. (2020). Neuroprotective potential of chrysin in Parkinson's disease: Molecular mechanisms and clinical implications. Neurochemistry International, 132, 104612. https://doi.org/10.1016/j.neuint.2019.104612
   PubMed Web of Science ®Google Scholar
• Baek, S. C., Park, M. H., Ryu, H. W., Lee, J. P., Kang, M. G., Park, C. M., Oh, S. R., & Kim, H. (2018). Rhamnocitrin isolated from Prunus padus var. seoulensis: A potent and selective reversible inhibitor of human monoamine oxidase A. Bioorganic Chemistry, 28, 317–325.
   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
• Blair, H. A., & Dhillon, S. (2017). Safinamide: A review in Parkinson's disease. CNS Drugs, 31(2), 169–176. https://doi.org/10.1007/s40263-017-0408-1
   PubMed Web of Science ®Google Scholar
• Carradori, S., & Silvestri, R. (2015). New frontiers in selective human MAO-B inhibitors. Journal of Medicinal Chemistry, 58(17), 6717–6732. https://doi.org/10.1021/jm501690r
   PubMed Web of Science ®Google Scholar
• Chan, H. H., Tse, M. K., Kumar, S., & Zhuo, L. (2018). A novel selective MAO-B inhibitor with neuroprotective and anti-Parkinsonian properties. European Journal of Pharmacology, 818, 254–262. https://doi.org/10.1016/j.ejphar.2017.10.023
   PubMed Web of Science ®Google Scholar
• Clarke, C. E. (2007). Parkinson's disease. BMJ (Clinical Research Edition), 335(7617), 441–445. https://doi.org/10.1136/bmj.39289.437454.AD
   PubMed Web of Science ®Google Scholar
• Dev, S., Parambi, D. G. T., Baby, B., Mathew, G. E., Hendawy, O. M., Joy, M., Sudev, S., & Mathew, B. (2020). An environmental synthesis of piperonal chalcones and their cytotoxic and antioxidant evaluation. Letters in Drug Design & Discovery, 17(2), 138–144. https://doi.org/10.2174/1570180815666181016155934
   Web of Science ®Google Scholar
• Ellman, G. L., Courtney, K. D., Andres, V., Jr., & Feather-Stone, R. M. (1961). New and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7, 88–95. https://doi.org/10.1016/0006-2952(61)90145-9
   PubMed Web of Science ®Google Scholar
• Joy, M., Mathew, B., & Sudarsanakumar, C. (2018). Structural features of Safinamide: A combined Hirshfeld surface analysis & quantum chemical treatment. Chemical Data Collection, 17-18, 404–414.
   Google Scholar
• Kalia, L. V., & Lang, A. E. (2015). Parkinson’s disease. The Lancet, 386(9996), 896–912. https://doi.org/10.1016/S0140-6736(14)61393-3
   PubMed Web of Science ®Google Scholar
• Lakshminarayanan, B., Baek, S. C., Lee, J. P., Kannappan, N., Mangiatordi, G. F., Nicolotti, O., Subburaju, T., Kim, H., & Mathew, B. (2019). Ethoxylated head of chalcones as a new class of multi-targeted MAO inhibitors. ChemistrySelect, 4(21), 6614–6619. https://doi.org/10.1002/slct.201901093
   Web of Science ®Google Scholar
• Mathew, B., Baek, S. C., Parambi, D. G. T., Lee Lee, J. P., Joy, M., Annie Rilda, P. R., Randev, R. V., Nithyamol, P., Vijayan, V., Inasu, S. T., Mathew, G. E., Lohidakshan, K. K., Kumar Krishnan, G., & Kim, H. (2018). Selected aryl thiosemicarbazones as a new class of multi-targeted monoamine oxidase inhibitors. MedChemComm, 9(11), 1871–1881. https://doi.org/10.1039/c8md00399h
   PubMed Web of Science ®Google Scholar
• Mathew, B., Baek, S. C., Thomas Parambi, D. G., Lee, J. P., Mathew, G. E., Jayanthi, S., Vinod, D., Rapheal, C., Devikrishna, V., Kondarath, S. S., Uddin, M. S., & Kim, H. (2019). Potent and highly selective dual-targeting monoamine oxidase-B inhibitors: Fluorinated chalcones of morpholine versus imidazole. Archiv Der Pharmazie, 352(4), e1800309. https://doi.org/10.1002/ardp.201800309
   PubMed Web of Science ®Google Scholar
• Mathew, B., Mathew, G. E., Suresh, J., Ucar, G., Sasidharan, R., Anbazhagan, S., K. Vilapurathu, J., & Jayaprakash, V. (2016). Monoamine oxidase inhibitors: Perspective design for the treatment of depression and neurological disorders. Current Enzyme Inhibition, 12(2), 115–122. https://doi.org/10.2174/1573408012666160402001715
   Google Scholar
• Mathew, B., Mathew, G. E., Uçar, G., Baysal, I., Suresh, J., Vilapurathu, J. K., Prakasan, A., Suresh, J. K., & Thomas, A. (2015). Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: Synthesis, biochemistry and molecular docking studies. Bioorganic Chemistry, 62, 22–29. https://doi.org/10.1016/j.bioorg.2015.07.001
   PubMed Web of Science ®Google Scholar
• Mathew, B., Parambi, D. G. T., Mathew, G. E., Uddin, M. S., Inasu, S. T., Kim, H., Marathakam, A., Unnikrishnan, M. K., & Carradori, S. (2019). Emerging therapeutic potentials of dual-acting MAO and AChE inhibitors in Alzheimer’s and Parkinson’s diseases. Archiv Der Pharmazie, 352(11), e1900177. https://doi.org/10.1002/ardp.201900177
   PubMed Web of Science ®Google Scholar
• Mathew, B., Suresh, J., Anbazhagan, S., & Chidambaranathan, N. (2016). Discovery of some novel imines of 2-amino, 5-thio, 1, 3, 4-thiadiazole as mucomembranous protector. Synthesis, anti-oxidant activity and in silico PASS approach. Journal of Saudi Chemical Society, 20, S426–S432. https://doi.org/10.1016/j.jscs.2013.01.002
   Web of Science ®Google Scholar
• Mathew, B., Uçar, G., Rapheal, C., Mathew, G. E., Joy, M., Machaba, K. E., & Soliman, M. E. S. (2017). Characterization of thienylchalcones as hMAO-B inhibitors: Synthesis, biochemistry and molecular dynamics studies. ChemistrySelect, 2(34), 11113–11119. https://doi.org/10.1002/slct.201702141
   Web of Science ®Google Scholar
• Mathew, G. E., Oh, J. M., Mohan, K., Kumudhavalli, M. V., Jayanthi, S., Kim, H., & Mathew, B. (2020). Inhibitions of monoamine oxidases and acetylcholinesterase by 1-methyl, 5-phenyl substituted thiosemicarbazones: Synthesis, biochemical, and computational investigations. Process Biochemistry. Doi: . https://doi.org/10.1016/j.procbio.2020.05.016
   Google Scholar
• Muller, T., & Mohr, J. D. (2019). Pharmacokinetics disease current status. Expert Opinion of Drug Metabolism and Toxicology, 15, 429–435.
   PubMed Web of Science ®Google Scholar
• Parambi, D. G. T., Oh, J. M., Baek, S. C., Lee, J. P., Tondo, A. R., Nicolotti, O., Kim, H., & Mathew, B. (2019). Design, synthesis and biological evaluation of oxygenated chalcones as potent and selective MAO-B inhibitors. Bioorganic Chemistry, 93, 103335. https://doi.org/10.1016/j.bioorg.2019.103335
   PubMed Web of Science ®Google Scholar
• Riederer, P., & Müller, T. (2018). Monoamine oxidase-B inhibitors in the treatment of Parkinson's disease: Clinical-pharmacological aspects. Journal of Neural Transmission (Vienna), 125(11), 1751–1757. https://doi.org/10.1007/s00702-018-1876-2
   PubMed Web of Science ®Google Scholar
• Sasidharan, R., Baek, S. C., Manju, S. L., Kim, H., & Mathew, B. (2018). Imidazole bearing chalcones as a new class of monoamine oxidase inhibitors. Biomedicine & Pharmacotherapy, 106, 8–13. https://doi.org/10.1016/j.biopha.2018.06.064
   PubMed Web of Science ®Google Scholar
• Schrödinger Release. (2017). Desmond molecular dynamics system, version 3: D.E. Shaw research: Maestro-Desmond interoperability tools. Schrödinger.
   Google Scholar
• Schrödinger Release. (2018). Glide, version 2. Schrödinger.
   Google Scholar
• Shulman, J. M., De Jager, P. L., & Feany, M. B. (2011). Parkinson's disease: Genetics and pathogenesis. Annual Review of Pathology, 6, 193–222. https://doi.org/10.1146/annurev-pathol-011110-130242
   PubMed Web of Science ®Google Scholar
• Suresh, J., Baek, S. C., Ramakrishnan, S. P., Kim, H., & Mathew, B. (2018). Discovery of potent and reversible MAO-B inhibitors as furanochalcones. International Journal of Biological Macromolecules, 108, 660–664. https://doi.org/10.1016/j.ijbiomac.2017.11.159
   PubMed Web of Science ®Google Scholar
• Tripathi, R. K., Rai, G. K., & Ayyannan, S. R. (2016). Exploration of a library of 3,4-(methylenedioxy)aniline-derived semicarbazones as dual inhibitors of monoamine oxidase and acetylcholinesterase: Design, synthesis, and evaluation. ChemMedChem., 11(11), 1145–1160. https://doi.org/10.1002/cmdc.201600128
   PubMed Web of Science ®Google Scholar
• Tripathi, R. K. P., M Sasi, V., Gupta, S. K., Krishnamurthy, S., & Ayyannan, S. R. (2018). Design, synthesis, and pharmacological evaluation of 2-amino-5-nitrothiazole derived semicarbazones as dual inhibitors of monoamine oxidase and cholinesterase: Effect of the size of aryl binding site. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 37–57. https://doi.org/10.1080/14756366.2017.1389920
   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
• Zheng, J., Zhang, X., & Zhen, X. (2019). Development of adenosine A2A receptor antagonists for the treatment of Parkinson's disease: A recent update and challenge. ACS Chemical Neuroscience, 10(2), 783–791. https://doi.org/10.1021/acschemneuro.8b00313
   PubMed Web of Science ®Google Scholar