Synthesis, spectroscopic analysis, and computational-based investigations on ‘azo-coumarin-Co(II)-galangin’ hybrids exhibit multipotential activities

References

• Ali, Y., Hamid, S. A., & Rashid, U. (2018). Biomedical applications of aromatic azo compounds. Mini Reviews in Medicinal Chemistry, 18(18), 1548–1558. https://doi.org/10.2174/1389557518666180524113111
   PubMed Web of Science ®Google Scholar
• Almatroodi, S. A., Almatroudi, A., Khan, A. A., Alhumaydhi, F. A., Alsahli, M. A., & Rahmani, A. H. (2020). Potential therapeutic targets of epigallocatechin gallate (EGCG), the most abundant catechin in green tea, and its role in the therapy of various types of cancer. Molecules (Basel, Switzerland), 25(14), 3146. https://doi.org/10.3390/molecules25143146
   PubMed Web of Science ®Google Scholar
• Anthony, E. J., Bolitho, E. M., Bridgewater, H. E., Carter, O. W. L., Donnelly, J. M., Imberti, C., Lant, E. C., Lermyte, F., Needham, R. J., Palau, M., Sadler, P. J., Shi, H., Wang, F. X., Zhang, W. Y., & Zhang, Z. (2020). Metallodrugs are unique: Opportunities and challenges of discovery and development. Chemical Science, 11(48), 12888–12917. https://doi.org/10.1039/d0sc04082g
   PubMed Web of Science ®Google Scholar
• Atanasov, A. G., Waltenberger, B., Pferschy-Wenzig, E. M., Linder, T., Wawrosch, C., Uhrin, P., Temml, V., Wang, L., Schwaiger, S., Heiss, E. H., Rollinger, J. M., Schuster, D., Breuss, J. M., Bochkov, V., Mihovilovic, M. D., Kopp, B., Bauer, R., Dirsch, V. M., & Stuppner, H. (2015). Discovery and resupply of pharmacologically active plant-derived natural products: A review. Biotechnology Advances, 33(8), 1582–1614. https://doi.org/10.1016/j.biotechadv.2015.08.001
   PubMed Web of Science ®Google Scholar
• Boros, E., Dyson, P. J., & Gasser, G. (2020). Classification of metal-based drugs according to their mechanisms of action. Chem, 6(1), 41–60. https://doi.org/10.1016/j.chempr.2019.10.013
   PubMed Web of Science ®Google Scholar
• Boy, S., Aras, A., Türkan, F., Akyıldırım, O., Beytur, M., Sedef Karaman, H., Manap, S., & Yüksek, H. (2021). Synthesis, spectroscopic analysis, and in vitro/in silico biological studies of novel piperidine derivatives heterocyclic Schiff-Mannich base compounds. Chemistry & Biodiversity, 18(12), e2100433. https://doi.org/10.1002/cbdv.202100433
   PubMed Web of Science ®Google Scholar
• Buczkowska, M., Bodtke, A., Lindequist, U., Gdaniec, M., & Bednarski, P. J. (2011). Cytotoxic and antimicrobial activities of Cu(II), Co(II), Pt(II) and Zn(II) Complexes with N,O-chelating heterocyclic carboxylates. Archiv Der Pharmazie, 344(9), 605–616. https://doi.org/10.1002/ardp.201100101
   PubMed Web of Science ®Google Scholar
• Cavasotto, C. N., & Di Filippo, J. I. (2021). Artificial intelligence in the early stages of drug discovery. Archives of Biochemistry and Biophysics, 698, 108730. https://doi.org/10.1016/j.abb.2020.108730
   PubMed Web of Science ®Google Scholar
• Edo, G. I., Ugbune, U., Onoharigho, F. O., Ezekiel, G. O., Ugbuwe, E., & Agbo, J. J. (2023). Investigation of the metal complexes and bioactive compound formed by coordination of bioactive phytochemical from ginger (Zingiber officinale) extracts to metal ions. Food Chemistry Advances, 3, 100337. https://doi.org/10.1016/j.focha.2023.100337
   Google Scholar
• El-Attar, M. S., Elshafie, H. S., Sadeek, S. A., El-Farargy, A. F., El-Desoky, S. I., El-Shwiniy, W. H., & Camele, I. (2022). Biochemical characterization and antimicrobial activity against some human or phyto-pathogens of new diazonium heterocyclic metal complexes. Chemistry & Biodiversity, 19(2), e202100785. https://doi.org/10.1002/cbdv.202100785
   PubMed Web of Science ®Google Scholar
• El-Baradie, K., El-Sharkawy, R., El-Ghamry, H., & Sakai, K. (2014). Synthesis and characterization of Cu(II), Co(II) and Ni(II) complexes of a number of sulfadrug azodyes and their application for wastewater treatment. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 121, 180–187. https://doi.org/10.1016/j.saa.2013.09.070
   PubMed Web of Science ®Google Scholar
• Fogel, D. B. (2018). Factors associated with clinical trials that fail and opportunities for improving the likelihood of success: A review. Contemporary Clinical Trials Communications, 11, 156–164. https://doi.org/10.1016/j.conctc.2018.08.001
   PubMed Web of Science ®Google Scholar
• Heffern, M. C., Yamamoto, N., Holbrook, R. J., Eckermann, A. L., & Meade, T. J. (2013). Cobalt derivatives as promising therapeutic agents. Current Opinion in Chemical Biology, 17(2), 189–196. https://doi.org/10.1016/j.cbpa.2012.11.019
   PubMed Web of Science ®Google Scholar
• Ismael, M., Abdel-Rahman, L. H., Abou El-Ezz, D., Ahmed, E. A., & Nafady, A. (2021). Synthesis, structural characterization, and biological studies of ATBS-M complexes (M(II) = Cu, Co, Ni, and Mn): Access for promising antibiotics and anticancer agents. Archiv Der Pharmazie, 354(4), e2000241. https://doi.org/10.1002/ardp.202000241
   PubMed Web of Science ®Google Scholar
• Jamil, W., Shaikh, J., Yousuf, M., Taha, M., Khan, K. M., & Shah, S. A. A. (2022). Synthesis, anti-diabetic and in silico QSAR analysis of flavone hydrazide Schiff base derivatives. Journal of Biomolecular Structure & Dynamics, 40(23), 12723–12738. https://doi.org/10.1080/07391102.2021.1975565
   PubMed Web of Science ®Google Scholar
• Jia, C. Y., Li, J. Y., Hao, G. F., & Yang, G. F. (2020). A drug-likeness toolbox facilitates ADMET study in drug discovery. Drug Discovery Today, 25(1), 248–258. https://doi.org/10.1016/j.drudis.2019.10.014
   PubMed Web of Science ®Google Scholar
• Kar, S., & Leszczynski, J. (2020). Open access in silico tools to predict the ADMET profiling of drug candidates. Expert Opinion on Drug Discovery, 15(12), 1473–1487. https://doi.org/10.1080/17460441.2020.1798926
   PubMed Web of Science ®Google Scholar
• Khan, T., & Gurav, P. (2017). PhytoNanotechnology: Enhancing delivery of plant based anti-cancer drugs. Frontiers in Pharmacology, 8, 1002. https://doi.org/10.3389/fphar.2017.01002
   PubMed Web of Science ®Google Scholar
• Kiriiri, G. K., Njogu, P. M., & Mwangi, A. N. (2020). Exploring different approaches to improve the success of drug discovery and development projects: A review. Future Journal of Pharmaceutical Sciences, 6(1), 27. https://doi.org/10.1186/s43094-020-00047-9
   Web of Science ®Google Scholar
• 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
   PubMedGoogle Scholar
• Lombardino, J. G., & Lowe, J. A. 3rd. (2004). The role of the medicinal chemist in drug discovery–then and now. Nature Reviews. Drug Discovery, 3(10), 853–862. https://doi.org/10.1038/nrd1523
   PubMed Web of Science ®Google Scholar
• Machado, D., Girardini, M., Viveiros, M., & Pieroni, M. (2018). Challenging the drug-likeness dogma for new drug discovery in tuberculosis. Frontiers in Microbiology, 9, 1367. https://doi.org/10.3389/fmicb.2018.01367
   PubMed Web of Science ®Google Scholar
• Mishra, S., Pandey, A., & Manvati, S. (2020). Coumarin: An emerging antiviral agent. Heliyon, 6(1), e03217. https://doi.org/10.1016/j.heliyon.2020.e03217
   PubMed Web of Science ®Google Scholar
• Mohammed, F. Z., Rizzk, Y. W., El Deen, I. M., Mourad, A. A. E., & El Behery, M. (2021). Design, synthesis, cytotoxic screening and molecular docking studies of novel hybrid thiosemicarbazone derivatives as anticancer agents. Chemistry & Biodiversity, 18(12), e2100580. https://doi.org/10.1002/cbdv.202100580
   PubMed Web of Science ®Google Scholar
• Motloung, D. M., Mashele, S. S., Matowane, G. R., Swain, S. S., Bonnet, S. L., Noreljaleel, A. E. M., Oyedemi, S. O., & Chukwuma, C. I. (2020). Synthesis, characterization, antidiabetic and antioxidative evaluation of a novel Zn(II)-gallic acid complex with multi-facet activity. The Journal of Pharmacy and Pharmacology, 72(10), 1412–1426. https://doi.org/10.1111/jphp.13322
   PubMed Web of Science ®Google Scholar
• Newman, D. J., & Cragg, G. M. (2020). Natural products as sources of new drugs over the nearly four decades from 01/1981 to 09/2019. Journal of Natural Products, 83(3), 770–803. https://doi.org/10.1021/acs.jnatprod.9b01285
   PubMed Web of Science ®Google Scholar
• Ng, P. Q., Ling, L. S. C., Chellian, J., Madheswaran, T., Panneerselvam, J., Kunnath, A. P., Gupta, G., Satija, S., Mehta, M., Hansbro, P. M., Collet, T., Dua, K., & Chellappan, D. K. (2020). Applications of nanocarriers as drug delivery vehicles for active phytoconstituents. Current Pharmaceutical Design, 26(36), 4580–4590. https://doi.org/10.2174/1381612826666200610111013
   PubMed Web of Science ®Google Scholar
• Nichols, P. L. (2021). Automated and enabling technologies for medicinal chemistry. Progress in Medicinal Chemistry, 60, 191–272. https://doi.org/10.1016/bs.pmch.2021.01.003
   PubMedGoogle Scholar
• Palermo, G., Spinello, A., Saha, A., & Magistrato, A. (2021). Frontiers of metal-coordinating drug design. Expert Opinion on Drug Discovery, 16(5), 497–511. https://doi.org/10.1080/17460441.2021.1851188
   PubMed Web of Science ®Google Scholar
• Plenge, R. M. (2016). Disciplined approach to drug discovery and early development. Science Translational Medicine, 8(349), 349ps15. https://doi.org/10.1126/scitranslmed.aaf2608
   PubMed Web of Science ®Google Scholar
• Ramorobi, L. M., Matowane, G. R., Mashele, S. S., Swain, S. S., Makhafola, T. J., Mfengwana, P. H., & Chukwuma, C. I. (2022). Zinc(II)-syringic acid complexation synergistically exerts antioxidant action and modulates glucose uptake and utilization in L-6 myotubes and rat muscle tissue. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 154, 113600. https://doi.org/10.1016/j.biopha.2022.113600
   PubMed Web of Science ®Google Scholar
• Roy, S., Das, S. K., & Chattopadhyay, B. (2018). Cobalt(II)-based metalloradical activation of 2-(diazomethyl)pyridines for radical transannulation and cyclopropanation. Angewandte Chemie (International ed. in English), 57(8), 2238–2243. https://doi.org/10.1002/anie.201711209
   PubMed Web of Science ®Google Scholar
• Sahoo, A., Fuloria, S., Swain, S. S., Panda, S. K., Sekar, M., Subramaniyan, V., Panda, M., Jena, A. K., Sathasivam, K. V., & Fuloria, N. K. (2021). Potential of marine terpenoids against SARS-CoV-2: An in silico drug development approach. Biomedicines, 9(11), 1505. https://doi.org/10.3390/biomedicines9111505
   PubMed Web of Science ®Google Scholar
• Sahoo, J., & Paidesetty, S. K. (2017). Biological investigation of novel metal complexes of 2-amino-4-substituted phenylthiazole Schiff bases. Journal of Taibah University Medical Sciences, 13(2), 142–155. https://doi.org/10.1016/j.jtumed.2017.10.007
   PubMedGoogle Scholar
• Sahoo, A., Swain, S. S., Paital, B., & Panda, M. (2022). Combinatorial approach of vitamin C derivative and anti-HIV drug-darunavir against SARS-CoV-2. Frontiers in Bioscience (Landmark Edition), 27(1), 10. https://doi.org/10.31083/j.fbl2701010
   PubMed Web of Science ®Google Scholar
• Sahoo, A., Swain, S. S., Panda, S. K., Hussain, T., Panda, M., & Rodrigues, C. F. (2022). In silico identification of potential insect peptides against biofilm-producing Staphylococcus aureus. Chemistry & Biodiversity, 19(10), e202200494. https://doi.org/10.1002/cbdv.202200494
   PubMed Web of Science ®Google Scholar
• Seyhan, A. A. (2019). Lost in translation: The valley of death across preclinical and clinical divide –identification of problems and overcoming obstacles. Translational Medicine Communications, 4(1). https://doi.org/10.1186/s41231-019-0050-7
   Google Scholar
• Shalash, A. M., & Abu Ali, H. I. (2017). Synthesis, crystallographic, spectroscopic studies and biological activity of new cobalt(II) complexes with bioactive mixed sulindac and nitrogen-donor ligands. Chemistry Central Journal, 11(1), 40. https://doi.org/10.1186/s13065-017-0268-2
   PubMedGoogle Scholar
• Stefanachi, A., Leonetti, F., Pisani, L., Catto, M., & Carotti, A. (2018). Coumarin: A natural, privileged and versatile scaffold for bioactive compounds. Molecules (Basel, Switzerland), 23(2), 250. https://doi.org/10.3390/molecules23020250
   PubMed Web of Science ®Google Scholar
• Sun, H., Liu, Z., Zhao, H., & Ang, E. L. (2015). Recent advances in combinatorial biosynthesis for drug discovery. Drug Design, Development and Therapy, 9, 823–833. https://doi.org/10.2147/DDDT.S63023
   PubMed Web of Science ®Google Scholar
• Swain, S. S., & Hussain, T. (2022). Combined bioinformatics and combinatorial chemistry tools to locate drug-able anti-tb phytochemicals: A cost-effective platform for natural product-based drug discovery. Chemistry & Biodiversity, 19(11), e202200267. https://doi.org/10.1002/cbdv.202200267
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Hussain, T., & Pati, S. (2021). Drug-lead anti-tuberculosis phytochemicals: A systematic review. Current Topics in Medicinal Chemistry, 21(20), 1832–1868. https://doi.org/10.2174/1568026621666210705170510
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Paidesetty, S. K., Dehury, B., Das, M., Vedithi, S. C., & Padhy, R. N. (2020). Computer-aided synthesis of dapsone-phytochemical conjugates against dapsone-resistant Mycobacterium leprae. Scientific Reports, 10(1), 6839. https://doi.org/10.1038/s41598-020-63913-9
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Paidesetty, S. K., Dehury, B., Sahoo, J., Vedithi, S. C., Mahapatra, N., Hussain, T., & Padhy, R. N. (2018). Molecular docking and simulation study for synthesis of alternative dapsone derivative as a newer antileprosy drug in multidrug therapy. Journal of Cellular Biochemistry, 119(12), 9838–9852. https://doi.org/10.1002/jcb.27304
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Paidesetty, S. K., & Padhy, R. N. (2017). Antibacterial activity, computational analysis and host toxicity study of thymol-sulfonamide conjugates. Biomedicine & Pharmacotherapy = Biomedecine & Pharmacotherapie, 88, 181–193. https://doi.org/10.1016/j.biopha.2017.01.036
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Panda, S. K., & Luyten, W. (2021). Phytochemicals against SARS-CoV as potential drug leads. Biomedical Journal, 44(1), 74–85. https://doi.org/10.1016/j.bj.2020.12.002
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Pati, S., & Hussain, T. (2022). Quinoline heterocyclic containing plant and marine candidates against drug-resistant Mycobacterium tuberculosis: A systematic drug-ability investigation. European Journal of Medicinal Chemistry, 232, 114173. https://doi.org/10.1016/j.ejmech.2022.114173
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Rout, S. S., Sahoo, A., Oyedemi, S. O., & Hussain, T. (2022). Antituberculosis, antioxidant and cytotoxicity profiles of quercetin: A systematic and cost-effective in silico and in vitro approach. Natural Product Research, 36(18), 4763–4767. https://doi.org/10.1080/14786419.2021.2008387
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Singh, S. R., Sahoo, A., Hussain, T., & Pati, S. (2022). Anti-HIV-drug and phyto-flavonoid combination against SARS-CoV-2: A molecular docking-simulation base assessment. Journal of Biomolecular Structure & Dynamics, 40(14), 6463–6476. https://doi.org/10.1080/07391102.2021.1885495
   PubMed Web of Science ®Google Scholar
• Swain, S. S., Singh, S. R., Sahoo, A., Panda, P. K., Hussain, T., & Pati, S. (2022b). Integrated bioinformatics-cheminformatics approach toward locating pseudo-potential antiviral marine alkaloids against SARS-CoV-2-Mpro. Proteins, 90(9), 1617–1633. https://doi.org/10.1002/prot.26341
   PubMed Web of Science ®Google Scholar
• Tahir, T., Ashfaq, M., Saleem, M., Rafiq, M., Shahzad, M. I., Kotwica-Mojzych, K., & Mojzych, M. (2021). Pyridine Scaffolds, phenols and derivatives of azo moiety: Current therapeutic perspectives. Molecules (Basel, Switzerland), 26(16), 4872. https://doi.org/10.3390/molecules26164872
   PubMed Web of Science ®Google Scholar
• Vamathevan, J., Clark, D., Czodrowski, P., Dunham, I., Ferran, E., Lee, G., Li, B., Madabhushi, A., Shah, P., Spitzer, M., & Zhao, S. (2019). Applications of machine learning in drug discovery and development. Nature Reviews. Drug Discovery, 18(6), 463–477. https://doi.org/10.1038/s41573-019-0024-5
   PubMed Web of Science ®Google Scholar
• Wooller, S. K., Benstead-Hume, G., Chen, X., Ali, Y., & Pearl, F. M. G. (2017). Bioinformatics in translational drug discovery. Bioscience Reports, 37(4), BSR20160180. https://doi.org/10.1042/BSR20160180
   PubMedGoogle Scholar
• Wright, P. M., Seiple, I. B., & Myers, A. G. (2014). The evolving role of chemical synthesis in antibacterial drug discovery. Angewandte Chemie (International ed. in English), 53(34), 8840–8869. https://doi.org/10.1002/anie.201310843
   PubMed Web of Science ®Google Scholar
• Wu, F., Zhou, Y., Li, L., Shen, X., Chen, G., Wang, X., Liang, X., Tan, M., & Huang, Z. (2020). Computational approaches in preclinical studies on drug discovery and development. Frontiers in Chemistry, 8, 726. https://doi.org/10.3389/fchem.2020.00726
   PubMed Web of Science ®Google Scholar