The computational study of the tautomerization of Dacarbazine in a biological system: The DFT approach

Document Type : Research Article

Authors

1 Department of Chemistry, Kerman Branch, Islamic Azad University, Kerman, Iran

2 Department of Chemistry, Kerman Branch, Islamic Azad University, Kerman, Iran,

Abstract

The aim of this study was to examine dacarbazine tautomerization with the density functional theory, where two tautomer structures have been indicated. The B3LYP/ 6-311G++ (d, p) , 6-311(d, p), and 6-311 quantum methods were considered to calculate the relative energies transferred between two structures. Also, calculations of the HOMO, LUMO, as well as the structures’ band gap energy were performed. Estimation of electronic parameters, such as electrophilicity, electronegativity, softness, and hardness, were also investigated to determine the compound’s reactivity in a biological media.

Graphical Abstract

The computational study of the tautomerization of Dacarbazine in a biological system: The DFT approach

Highlights

  • Applying a theoretical investigation to the tautomerization mechanism
  • Applying an accurate method by diffuse orbitals
  • Calculation of physico-chemical parameters
  • Simulation of biochemistry media

Keywords

References

[1] A. Murray, Dacarbazine, Manchester University College of Pharmacy, Fort Wayne, IN, USA 2014 (2014) 1132-1134.
[2] M. Song, R.Y. Zhang, X.M. Wang, Nano-titanium dioxide enhanced biosensing of the interaction of dacarbazine with DNA and DNA bases, Mater. Lett. 60 (2006) 2143-2147.
[3] R.Y. Zhang, X.M. Wang, S.J. Gong, A voltammetric study of the effect of gold nanoparticles on the binding of DTIC to DNA bases, Electrochem. Solid St. 7 (2004) J27.
[4] Q. Shen, X. Wang, D. Fu, The amplification effect of functionalized gold nanoparticles on the binding of anticancer drug dacarbazine to DNA and DNA bases, Appl. Surf. Sci. 255 (2008) 577-580.
[5] G. Bonadonna, R. Zucali, S. Monfardini, M.d. Lena, C. Uslenghi, Combination chemotherapy of Hodgkin’s disease with adriamycin, bleomycin, vinblastine, and imidazole carboxamide versus MOPP, Cancer, 36 (1975) 252-259.
[6] R. Advani, Optimal therapy of advanced Hodgkin lymphoma, Hematology, the American Society of Hematology Education Program Book, 2011, pp. 310-316.
[7] K. Bauer, N. Skoetz, I. Monsef, A. Engert, C. Brillant, Cochrane Database of Systematic Reviews, John Wiley & Sons Ltd., Chichester, UK, 1996.
[8] P.P. Saunders, G.A. Schultz, Role of 4-diazoimidazole-5-carboxamide in the action of the antitumor agent 5 (4)-(3,3-dimethyl-1-triazeno) imidazole-4-(5) carboxa-mide in Bacillus subtilis, Biochem. Pharmacol. 21 (1972) 2065-2076.
[9] G. Boysen, B.F. Pachkowski, J. Nakamura, J.A. Swenberg, The formation and biological significance of N7-guanine adducts, Mutat. Res. 678 (2009) 76-94.
[10] T.A. Connors, P.M. Goddard, K. Merai, W.C.J. Ross, D.E.V. Wilman, Tumour inhibitory triazenes: structural requirements for an active metabolite, Biochem. Pharmacol. 25 (1976) 241-246.
[11] H.C. Freeman, N.D. Hutchinson, The crystal structure of the anti-tumor agent 5-(3,3-dimethyl-1-triazenyl) imidazole-4-carboxamide, Acta Crystallogr. B 35 (1979) 2051-2054.
[12] J.N. Latosińska, M. Latosińska, J. Seliger, V. Žagar, D.V. Burchardt, K. Derwich, Unusual case of desmotropy. Combined spectroscopy (1H-14N NQDR) and quantum chemistry (periodic hybrid DFT/QTAIM and Hirshfeld surface-based) study of solid dacarbazine (anti-neoplastic), Solid State Nucl. Mag. 68-69 (2015) 13-24.
[13] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, Gaussian 09, Revision D.01, Gaussian Inc., Wallingford CT (2009) 201.
Journal of Particle Science and Technology
Volume 6, Issue 1
April 2020
Pages 55-60

Files

History

  • Receive Date: 09 January 2021
  • Revise Date: 13 April 2021
  • Accept Date: 23 April 2021

Share

How to cite

Statistics