Issue

Vol. 25 No. 5 (2013): Vol 25 Issue 5

Copyright (c) 2013 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Theoretical Study on Interactions Between Berberine as an Anticancer Drug and DNA

https://doi.org/10.14233/ajchem.2013.13529
A. Parchehbaf Jadid
Department of Applied Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran
Leila Zarefatin
Department of Applied Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran
Leila Javadi
Department of Applied Chemistry, Ardabil Branch, Islamic Azad University, Ardabil, Iran

Asian Journal of Chemistry, Vol. 25 No. 5 (2013): Vol 25 Issue 5

Abstract

In this study, we present the work on the physicochemical interaction between the anticancer alkaloid berberine (BRB) and DNA with the purpose of designing drugs that interact more with DNA. Molecular modeling on the complex formed between berberine and DNA presented that this complex was undeniably fully able of participating in the formation of a stable intercalation site. Besides, the molecular geometries of berberine and the DNA bases (adenine, guanine, cytosine and thymine) were optimized with the aid of the B3LYP/6-31G method. This intercalator has a large polarizability and is a good electron acceptor, while base pairs are good electron donors. B3LYP/6-31G stabilization energies of intercalator… DNA base pair complexes are large (-7.65 kcal/mol for AT···BRB and -3.58 kcal/mol for GC···BRB). It was eventually concluded that the dispersion energy and the electrostatic interaction influenced the stability of the intercalator···DNA base pair complexes. The results exhibited that the berberine changes affected the DNA structure with reference to the bond length, the bond angle, the torsion angle and the charges.

Keywords

DNA Intercalator Berberine Density functional theory
Parchehbaf Jadid, A., Zarefatin, L., & Javadi, L. (2012). Theoretical Study on Interactions Between Berberine as an Anticancer Drug and DNA. Asian Journal of Chemistry, 25(5), 2615–2621. https://doi.org/10.14233/ajchem.2013.13529
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. D.S. Bhakuni and S. Jain, In ed.: A. Brossi, The Alkaloids, Academic Press, New York, Vol. 28, p. 95 (1986).
  2. W.A. Creasy, Biochem. Pharmacol., 28, 1081 (1979).
  3. X. Tian, Y. Song, H. Dong and Y. Baoxian, Bioelectrochemistry, 73, 18 (2008).
  4. M. Meyerson, J. Clin. Oncol., 18, 2626 (2000).
  5. C.L. Kuo, C.C. Chou and B.Y. Yung, Cancer. Lett., 93, 193 (1995).
  6. I.W. Yang, C.C. Chou and B.Y. Yung, Arch. Pharmacol., 354, 102 (1996).
  7. S. Letasiova, S. Jantova, L. Cipak and M. Muckova, Cancer Lett., 239, 254 (2006).
  8. P.-L. Peng, Y.-S. Hsieh, C.-J.Wang, J.-L. Hsu and F.-P. Chou, Appl. Pharmacol., 214, 8 (2006).
  9. M.M. Islam, R. Sinha and G.S. Kumar, Biophys. Chem., 125, 508 (2007).
  10. T.-K. Li, E. Bathory, E.J. LaVoie, A.R. Srinivasan, W.K. Olson, R.R. Sauers, L.F. Liu and D.S. Pilch, Biochemistry, 39, 7107 (2000).
  11. S. Mazzini, M.C. Bellucci and R. Mondelli, Bioorg. Med. Chem., 11, 505 (2003).
  12. K. Bhadra, G. Suresh Kumar, S. Das, Md. M. Islam and M. Maiti, Bioorg. Med. Chem., 13, 4851 (2005).
  13. M.W. Davidson, I. Lopp, S. Alexander and W.D. Wilson, Nucl. Acids Res., 4, 2697 (1977).
  14. D. Debnath, G. Suresh Kumar, R. Nandi and M. Maiti, Indian J. Biochem. Biophys., 26, 201 (1989).
  15. A. Saran, S. Srivastava, E. Coutinho and M. Maiti, Indian J. Biochem. Biophys., 32, 74 (1995).
  16. F.M. Chen, J. Biomol. Struct. Dyn., 1, 925 (1983).
  17. G.T. Walker, M.P. Stone and T.R. Krugh, Biochemistry, 24, 746 (1985).
  18. C.C. Hardin, G.T. Walker and I. Tinoco Jr., Biochemistry, 27, 4178 (1988).
  19. J.B. Chaires, J. Biol. Chem., 261, 8899 (1986).
  20. E. Jimenez-Garcia and J. Portugal, Biochemistry, 31, 11641 (1992).
  21. U. Diederichsen, Angew. Chem. Int. Ed., 36, 2317 (1997).
  22. J.B. Chaires, Biophys. Chem., 35, 191 (1990).
  23. M.P. Fontaine-Aupart, H. Laguitton-Pasquier, R. Pansu, L. Brain, E. Renault, M.C. Marden and C. Rivalle, J. Chem. Soc. Perkin. Trans. II, 1767 (1996).
  24. J. Dolenc, U. Borstnik, M. Hodoscek, J. Koller and D. Janezic, J. Mol. Struct. (Theochem.), 718, 77 (2005).
  25. M. Elstner, P. Hobza, T. Frauenheim, S. Suhai and E. Kaxiras, J. Chem. Phys., 114, 5149 (2001).
  26. T.M. EL-Gogary, Ph.D. Thesis, The Role of Charge Transfer Complex Formation on the Overall Structure Activity Relationships of DNA Radioprotectants and radiosensitizers. Mansoura University, Egypt/De Montfort University, Leicester, UK (1998).
  27. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam,A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, 34567 J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle and J.A. Pople, Gaussian Inc. Pittsburgh PA (1998).
  28. C. Bayly, P. Cieplak, W.D. Cornell and P.A. Kollman, J. Phys. Chem., 97, 10269 (1993).
  29. W.D. Cornell, P. Cieplak, C.I. Bayly, I.R. Gould, K.M. Merz, D.M. Ferguson, D.C. Spellmeyer, T. Fox, J.W. Caldwell and P.A. Kollman, J. Am. Chem. Soc., 117, 5179 (1995).
  30. P. Hobza, J. Sponer and T. Reschel, J. Comput. Chem., 16, 1315 (1995).
  31. M. Elstner, P. Hobza, T. Frauenheim, S. Suhai and E. Kaxiras, J. Chem. Phys., 114, 5149 (2001).
  32. P. Hobza and R. Zahradnik, Intermolecular Complexes, Elsevier, Amsterdam (1988).
  33. J.G.C.M. van Duijneveldt-van de Rijdt, F.B. van Duijneveldt and J.H. van Lenthe, Chem. Rev., 94, 1873 (1994).
  34. U. Bren, M. Zupan, F.P. Guengerich and J. Mavri, J. Org. Chem., 71, 4078 (2006).
  35. U. Bren, F.P. Guengerich and J. Mavri,Chem. Res. Toxicol., 20, 1134 (2007).
  36. M.J. Frisch, J.E. Del-Bene, J.S. Binkley and H.F. Schaefer, J. Chem. Phys., 84, 2279 (1986).
  37. D.W. Schwenke and D.G. Truhlar, J. Chem. Phys., 82, 2418 (1985).
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0