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26/02/2025
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Bùi, T. T., Nguyễn, T. P., Mai, T. Q. A., & Bùi, T. H. (2025). Evaluating the anticancer effects of compounds from Celastrus hindsii Benth. on liver cancer using molercular docking method. Viet Nam Journal of Traditional Medicine and Pharmacy, 59(01), 63-72. https://doi.org/10.60117/vjmap.v59i01.357
Evaluating the anticancer effects of compounds from Celastrus hindsii Benth. on liver cancer using molercular docking method
Main Article Content
Abstract
Objectives: To evaluate the inhibitory effects on human multidrug resistance protein 1 (hMRP1) of 41 compounds isolated from Black Plum through previously published studies.
Subjects and methods: Molecular docking screening were conducted using Autodock Vina software. The Lipinski's rule of five was employed to assess drug-likeness properties of compounds with lower docking scores than the reference compound. Pharmacokinetic-toxicity parameters of drug-like compounds were evaluated using pkCSM tool.
Results: Results indicated two compounds, Triptobenzene A and (−)–Epiafzelechin, with significantly low binding energies (∆G = -6.6 kcal/mol and -6.5 kcal/mol) after screening. Lipinski analysis revealed drug-like properties for both compounds. Predicted pharmacokinetic-toxicity parameters also suggested excellent gut absorption and non-toxicity for these compounds. Biological activity estimation indicated moderate to good activity for both compounds.
Conclusions: Therefore, these two compounds Triptobenzene A and (−)–Epiafzelechin have the potential to become future therapeutics for liver cancer
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References
1. Bộ Y tế. Hướng dẫn chẩn đoán và điều trị ung thư biểu mô tế bào gan, 2020.
2. Johnson, Z.L. and J. Chen. Structural Basis of Substrate Recognition by the Multidrug Resistance Protein MRP1. Cell, 2017, 168(6), pp. 1075-1085,e9.
3. Ramaen, O., et al. Structure of the human multidrug resistance protein 1 nucleotide binding domain 1 bound to Mg2+/ATP reveals a non-productive catalytic site. J Mol Biol, 2006, 359(4), pp.940-949.
4. Shen, Y., et al., Traditional uses, secondary metabolites, and pharmacology of Celastrus species-a review. Journal of ethnopharmacology, 2019, 241: p. 111934-112009
5. Ferreira, L.G., et al. Molecular docking and structure-based drug design strategies. Molecules, 2015, 20(7), pp.13384-13421.
6. Chen, C.-j., et al. Internal duplication and homology with bacterial transport proteins in the mdr1 (P-glycoprotein) gene from multidrug-resistant human cells. Cell, 1986, 47(3), pp.381-389.
7. Cole, S.P., et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science, 1992, 258(5088), pp.1650-1654.
8. Dhasmana, D., et al. Targeting Nucleotide Binding Domain of Multidrug Resistance-associated Protein-1 (MRP1) for the Reversal of Multi Drug Resistance in Cancer. Sci Rep, 2018, 8(1), pp. 11973.
9. Tsuruo, T., et al. Enhancement of vincristine-and adriamycin-induced cytotoxicity by verapamil in P388 leukemia and its sublines resistant to vincristine and adriamycin. Biochem Pharmacol, 1982, 31(19), pp.3138-3140.
10. Häußermann, K., et al. Effects of verapamil enantiomers and major metabolites on the cytotoxicity of vincristine and daunomycin in human lymphoma cell lines. Eur J Clin Pharmacol, 1991, 40, pp. 53-59.
11. Eichelbaum, M., et al. Phase I studie mit R-verapamil zur aufhebung der multidrug-resistenz bei chemotherapie, 1993, pp. 51-56.
12. Schumacher, K., et al. Reversal of multidrug resistance by R-verapamil. in Acute Leukemias IV: Prognostic Factors and Treatment Strategies, 1994, Springer.
13. Pires, D.E., T.L. Blundell, and D.B. Ascher. pkCSM: Predicting Small-Molecule Pharmacokinetic and Toxicity Properties Using Graph-Based Signatures. J Med Chem, 2015, 58(9), pp. 4066-4072.
14. Prakash, C., et al. Identification of the major human liver cytochrome P450 isoform(s) responsible for the formation of the primary metabolites of ziprasidone and prediction of possible drug interactions. Br J Clin Pharmacol, 2000, 49 Suppl 1(Suppl 1), pp. 35s-42s.
15. Takaishi, Y., et al. Phenolic diterpenes from Tripterygium wilfordii var. regelii. Phytochemistry, 1997, 45(5), pp. 979-984.
16. Rodríguez, B.J.M.R.i.C. 1H and 13C NMR spectral assignments of some natural abietane diterpenoids. Magn Reson Chem, 2003, 41(9), pp. 741-746.
17. Yang, X.-W., et al. Isolation, structure, and bioactivities of abiesadines A–Y, 25 new diterpenes from Abies georgei Orr. Bioorg Med Chem, 2010, 18(2), pp. 744-754.
18. Burmistrova, O., et al. Antiproliferative activity of abietane diterpenoids against human tumor cells. J Nat Prod, 2013, 76(8), pp. 1413-1423.
19. Kafil, V., et al. Abietane diterpenoid of Salvia sahendica Boiss and Buhse potently inhibits MCF-7 breast carcinoma cells by suppression of the PI3K/AKT pathway. RSC advances, 2015, 5(23), pp. 18041-18050.
20. Zhang, G.-J., et al. Anti-Coxsackie virus B diterpenes from the roots of Illicium jiadifengpi. Tetrahedron, 2013, 69(3), pp. 1017-1023.
21. Zhang, G.-J., et al. Diterpenes and sesquiterpenes with anti-Coxsackie virus B3 activity from the stems of Illicium jiadifengpi. Tetrahedron, 2014, 70(30), pp. 4494-4499.
22. González, M.A. and R.J.J.J.o.n.p. Zaragoza. Semisynthesis of the antiviral abietane diterpenoid jiadifenoic acid C from callitrisic acid (4-epidehydroabietic acid) isolated from sandarac resin. J Nat Prod, 2014, 77(9), pp. 2114-2117.
23. Wang, Y.-D., et al. Diterpenoids and sesquiterpenoids from the roots of Illicium majus. J Nat Prod , 2013, 76(10), pp. 1976-1983.
24. Pferschy-Wenzig, E.M., et al. In vitro anti-inflammatory activity of larch (Larix decidua L.) sawdust. J Agric Food Chem,2008, 56(24), pp. 11688-11693.
25. Fan, D., et al. New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii. Int J Mol Sci, 2017, 18(1), pp. 147.
26. Aron, P.M. and J.A. Kennedy. Flavan-3-ols: nature, occurrence and biological activity. Mol Nutr Food Res, 2008, 52(1), pp. 79-104.
27. Hori, K., et al. Antioxidant phenolic compounds from the rhizomes of Astilbe rivularis. Nat Prod Res, 2018, 32(4), pp. 453-456.
28. Min, K.R., et al. (-)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus. Planta Med, 1999, 65(5), pp. 460-2.
2. Johnson, Z.L. and J. Chen. Structural Basis of Substrate Recognition by the Multidrug Resistance Protein MRP1. Cell, 2017, 168(6), pp. 1075-1085,e9.
3. Ramaen, O., et al. Structure of the human multidrug resistance protein 1 nucleotide binding domain 1 bound to Mg2+/ATP reveals a non-productive catalytic site. J Mol Biol, 2006, 359(4), pp.940-949.
4. Shen, Y., et al., Traditional uses, secondary metabolites, and pharmacology of Celastrus species-a review. Journal of ethnopharmacology, 2019, 241: p. 111934-112009
5. Ferreira, L.G., et al. Molecular docking and structure-based drug design strategies. Molecules, 2015, 20(7), pp.13384-13421.
6. Chen, C.-j., et al. Internal duplication and homology with bacterial transport proteins in the mdr1 (P-glycoprotein) gene from multidrug-resistant human cells. Cell, 1986, 47(3), pp.381-389.
7. Cole, S.P., et al. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science, 1992, 258(5088), pp.1650-1654.
8. Dhasmana, D., et al. Targeting Nucleotide Binding Domain of Multidrug Resistance-associated Protein-1 (MRP1) for the Reversal of Multi Drug Resistance in Cancer. Sci Rep, 2018, 8(1), pp. 11973.
9. Tsuruo, T., et al. Enhancement of vincristine-and adriamycin-induced cytotoxicity by verapamil in P388 leukemia and its sublines resistant to vincristine and adriamycin. Biochem Pharmacol, 1982, 31(19), pp.3138-3140.
10. Häußermann, K., et al. Effects of verapamil enantiomers and major metabolites on the cytotoxicity of vincristine and daunomycin in human lymphoma cell lines. Eur J Clin Pharmacol, 1991, 40, pp. 53-59.
11. Eichelbaum, M., et al. Phase I studie mit R-verapamil zur aufhebung der multidrug-resistenz bei chemotherapie, 1993, pp. 51-56.
12. Schumacher, K., et al. Reversal of multidrug resistance by R-verapamil. in Acute Leukemias IV: Prognostic Factors and Treatment Strategies, 1994, Springer.
13. Pires, D.E., T.L. Blundell, and D.B. Ascher. pkCSM: Predicting Small-Molecule Pharmacokinetic and Toxicity Properties Using Graph-Based Signatures. J Med Chem, 2015, 58(9), pp. 4066-4072.
14. Prakash, C., et al. Identification of the major human liver cytochrome P450 isoform(s) responsible for the formation of the primary metabolites of ziprasidone and prediction of possible drug interactions. Br J Clin Pharmacol, 2000, 49 Suppl 1(Suppl 1), pp. 35s-42s.
15. Takaishi, Y., et al. Phenolic diterpenes from Tripterygium wilfordii var. regelii. Phytochemistry, 1997, 45(5), pp. 979-984.
16. Rodríguez, B.J.M.R.i.C. 1H and 13C NMR spectral assignments of some natural abietane diterpenoids. Magn Reson Chem, 2003, 41(9), pp. 741-746.
17. Yang, X.-W., et al. Isolation, structure, and bioactivities of abiesadines A–Y, 25 new diterpenes from Abies georgei Orr. Bioorg Med Chem, 2010, 18(2), pp. 744-754.
18. Burmistrova, O., et al. Antiproliferative activity of abietane diterpenoids against human tumor cells. J Nat Prod, 2013, 76(8), pp. 1413-1423.
19. Kafil, V., et al. Abietane diterpenoid of Salvia sahendica Boiss and Buhse potently inhibits MCF-7 breast carcinoma cells by suppression of the PI3K/AKT pathway. RSC advances, 2015, 5(23), pp. 18041-18050.
20. Zhang, G.-J., et al. Anti-Coxsackie virus B diterpenes from the roots of Illicium jiadifengpi. Tetrahedron, 2013, 69(3), pp. 1017-1023.
21. Zhang, G.-J., et al. Diterpenes and sesquiterpenes with anti-Coxsackie virus B3 activity from the stems of Illicium jiadifengpi. Tetrahedron, 2014, 70(30), pp. 4494-4499.
22. González, M.A. and R.J.J.J.o.n.p. Zaragoza. Semisynthesis of the antiviral abietane diterpenoid jiadifenoic acid C from callitrisic acid (4-epidehydroabietic acid) isolated from sandarac resin. J Nat Prod, 2014, 77(9), pp. 2114-2117.
23. Wang, Y.-D., et al. Diterpenoids and sesquiterpenoids from the roots of Illicium majus. J Nat Prod , 2013, 76(10), pp. 1976-1983.
24. Pferschy-Wenzig, E.M., et al. In vitro anti-inflammatory activity of larch (Larix decidua L.) sawdust. J Agric Food Chem,2008, 56(24), pp. 11688-11693.
25. Fan, D., et al. New Abietane and Kaurane Type Diterpenoids from the Stems of Tripterygium regelii. Int J Mol Sci, 2017, 18(1), pp. 147.
26. Aron, P.M. and J.A. Kennedy. Flavan-3-ols: nature, occurrence and biological activity. Mol Nutr Food Res, 2008, 52(1), pp. 79-104.
27. Hori, K., et al. Antioxidant phenolic compounds from the rhizomes of Astilbe rivularis. Nat Prod Res, 2018, 32(4), pp. 453-456.
28. Min, K.R., et al. (-)-Epiafzelechin: cyclooxygenase-1 inhibitor and anti-inflammatory agent from aerial parts of Celastrus orbiculatus. Planta Med, 1999, 65(5), pp. 460-2.