Design, Synthesis, Anticancer Activity and Molecular Docking of New 1,2,3-Triazole combined Glucosides with coumarin

Main Article Content

Ruaa Wassim Adam
Ezzat Hussein Zimam

Keywords

Carbohydrate, 4-hydroxy coumarin, Click chemistery,1,2,3-triazole

Abstract

The synthetic strategy for the preparation of the targeted glycosides involved two different pathways to obtain two types of hybrid compounds; the first represents new 1,2,3-triazole derivative in the 6-carbon glucopyranose, and the other is a new glycoside of 4-hydroxy coumarin bases. The starting derivative 1 prepared by reaction of 6-azide glucopyranose and 2 ethylene azide-2,3,4,6-tetraacetate- β-D- glucopyranoside with propargyl 4-hydroxy coumarin under click conditions .The cytotoxicity potentials of glucosides derivatives were evaluated by MTT assay against liver cancer primary tissue culture , which appear that derivatives exhibited selective cytotoxicity against liver cancer cells isolated from Iraqi patients with inhibitory concentration (IC50) 106.81 μg/ml. Docking simulation studies were performed to check the binding patterns of the synthesized compounds. Enzyme inhibition assay studies were also conducted for the epidermal growth factor receptor (EGFR), and the results explained the activity of a number of derivatives.

Abstract 183 | PDF Downloads 178

References

1. A. Zorin, L. Klenk, T. Mack, H.P. Deigner, and M. S. Schmidt, “Current Synthetic Approaches to the Synthesis of Carbasugars from Non-Carbohydrate Sources, Top. Curr. Chem., 2022, 380, 2, pp. 1–31.
2. A. F. Razaq and M. J. Mohammed, “Synthesis and Studying of the Biological Activity of Some New Coumarin-3-carboxylic Acid Heterocyclic Derivatives, Egypt. J. Chem., 2022, 65, 2, pp. 35–40.
3. M. M. Heravi, S. Khaghaninejad, and M. Mostofi, Pechmann reaction in the synthesis of coumarin derivatives,” in Advances in heterocyclic chemistry, 2014 , 112, Elsevier, , pp. 1–50.
4. M. Tolba et al., “An overview on synthesis and reactions of coumarin based compounds, Curr. Chem. Lett., 2022, 11, 1, pp. 29–42.
5. A. S. Barrow, C. J. Smedley, Q. Zheng, S. Li, J. Dong, and J. E. Moses, The growing applications of SuFEx click chemistry,” Chem. Soc. Rev., 2019 ,48, 17, pp. 4731–4758.
6. S. I. Presolski, V. P. Hong, and M. G. Finn, Copper‐catalyzed azide–alkyne click chemistry for bioconjugation,” Curr. Protoc. Chem. Biol., 2011 , 3, 4, pp. 153–162.
7. Y. Shi, X. Cao, and H. Gao, “The use of azide–alkyne click chemistry in recent syntheses and applications of polytriazole-based nanostructured polymers, Nanoscale, 2016, 8, ,9, pp. 4864–4881.
8. M. S. Singh, S. Chowdhury, and S. Koley, “Advances of azide-alkyne cycloaddition-click chemistry over the recent decade , Tetrahedron, 2016 , 72, 35, pp. 5257-5283
9. E. Bonandi, M. S. Christodoulou, G. Fumagalli, D. Perdicchia, G. Rastelli, and D. Passarella, “The 1, 2, 3-triazole ring as a bioisostere in medicinal chemistry, Drug Discov. Today, 2017 , 22, ,10, pp. 1572–1581.
10. F. Wei, W. Wang, Y. Ma, C.-H. Tung, and Z. Xu, “Regioselective synthesis of multisubstituted 1, 2, 3-triazoles: moving beyond the copper-catalyzed azide–alkyne cycloaddition, Chem. Commun., 2016 , 52, 99, pp. 14188–14199..
11. R. S. Gomes, G. A. M. Jardim, R. L. de Carvalho, M. H. Araujo, and E. N. da Silva Júnior, “Beyond copper-catalyzed azide-alkyne 1, 3-dipolar
cycloaddition: Synthesis and mechanism insights, Tetrahedron, 2019 , 75, 27, pp. 3697–3712.
12. J. El-Abid, V. Moreau, J. Kovensky, and V. Chagnault, “Effects of CoCl2 on the regioselective tosylation of oligosaccharides, J. Mol. Struct., 2021 ,1241, p. 130609.
13. V. Yarlagadda, M. M. Konai, G. B. Manjunath, C. Ghosh, and J. Haldar, “Tackling vancomycin-resistant bacteria with ‘lipophilic–vancomycin–carbohydrate conjugates, J. Antibiot. (Tokyo). 2015. 68, 5, pp. 302–312.
14. Z. D. Wang, Y. Mo, C.-L. Chiou, and M. Liu, “A simple preparation of 2, 3, 4, 6-tetra-O-acyl-gluco-, galacto-and mannopyranoses and relevant theoretical study, Molecules, 2010. 15, 1, pp. 374–384.
15. M. M. Zeydi, S. J. Kalantarian, and Z. Kazeminejad, “Overview on developed synthesis procedures of coumarin heterocycles, J. Iran. Chem. Soc., 2020., 17, 12, pp. 3031–3094.
16. S. Hao et al., “Design, synthesis and biological evaluation of novel carbohydrate-based sulfonamide derivatives as antitumor agents, Bioorg. Chem., 2020 ,104, p. 104237.
17. V. Aragão-Leoneti, V. L. Campo, A. S. Gomes, R. A. Field, and I. Carvalho, “Application of copper (I)-catalysed azide/alkyne cycloaddition (CuAAC)‘click chemistry’in carbohydrate drug and neoglycopolymer synthesis, Tetrahedron, 2010. 66, 49, pp. 9475–9492.
18. A. I. Mohammed, N. H. Mansour, and L. S. Mahdi, “Synthesis and antibacterial activity of 1-N-(β-d-glucopyranosyl)-4-((1-substituted-1H-1, 2, 3-triazol-4-yl) ethoxymethyl)-1, 2, 3-triazoles, Arab. J. Chem., 2017. 10, pp. S3508–S3514.
19. R. A. Friesner et al., “Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy, J. Med. Chem., 2004. 47, 7, pp. 1739–1749.
20. S. Release, “1: Maestro, Schrodinger, 2019 LLC, New York..
21. S. K. Burley et al., “RCSB Protein Data Bank: biological macromolecular structures enabling research and education in fundamental biology, biomedicine, biotechnology and energy, Nucleic Acids Res., 2019 ,47, D1, pp. D464–D474.
22. W. L. Jorgensen, D. S. Maxwell, and J. Tirado-Rives, “Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids, J. Am. Chem. Soc., 1996. 118, 45, pp. 11225–11236.
23. S. Release, “4: LigPrep, Schrödinger, 2019.LLC, New York, NY.
24. A. C. Kaushik, D. Gautam, A. S. Nangraj, D.-Q. Wei, and S. Sahi, “Protection of primarydopaminergic midbrain neurons through impact of small molecules using virtual screening of gpr139 supported by molecular dynamic simulation and systems biology, Interdiscip. Sci. Comput. Life Sci., 2019. 11, 2, pp. 247–257.
25. L. K. Williams, C. Li, S. G. Withers, and G. D. Brayer, “Order and disorder: differential structural impacts of myricetin and ethyl caffeate on human amylase, an antidiabetic target, J. Med. Chem., 2012, 55, 22, pp. 10177–10186.
26. T. Sander, J. Freyss, M. von Korff, and C. Rufener, “DataWarrior: an open-source program for chemistry aware data visualization and analysis, J. Chem. Inf. Model., 2015. 55, 2, pp. 460–473.
27. C.-F. Liu, Q.-K. Shen, J.-J. Li, Y.-S. Tian, and Z. Quan, “Synthesis and biological evaluation of novel 7-hydroxy-4-phenylchromen-2-one–linked to triazole moieties as potent cytotoxic agents, J. Enzyme Inhib. Med. Chem., 2017. 32, 1, pp. 1111–1119.
28. T. Hayon, A. Dvilansky, O. Shpilberg, and I. Nathan, “Appraisal of the MTT-based assay as a useful tool for predicting drug chemosensitivity in leukemia, Leuk. Lymphoma, 2003, 44, 11, pp. 1957–1962.
29. S. Kasibhatla, G. P. Amarante-Mendes, D. Finucane, T. Brunner, E. Bossy-Wetzel, and D. R. Green, “Acridine orange/ethidium bromide (AO/EB) staining to detect apoptosis,” Cold Spring Harb. Protoc., 2006, 3, p. 4493..
30. H. E. Hashem, A. E.-G. E. Amr, E. S. Nossier, M. M. Anwar, and E. M. Azmy, “New benzimidazole-, 1, 2, 4-triazole-, and 1, 3, 5-triazine-based derivatives as potential EGFRWT and EGFRT790M inhibitors: microwave-assisted synthesis, anticancer evaluation, and molecular docking study, ACS omega, 2022, 7, 8, pp. 7155–7171.
31. H. S. Mohammed, S. William, T. Aboushousha, H. M. A. Taleb, R. Sabour, and M. A. Ghareeb, “Ailanthus excelsa leaf extract: Chemical characterization, antischistosomal activity, and in silico study of isolated phenolic compounds as promising thioredoxin glutathione reductase inhibitors,,J. Appl. Pharm. Sci., 2023,13, 2, pp. 124–145.