Interaction of Carmustine Tautomers with Adenine - DFT Study

  • Lemi Türker Department of Chemistry, Middle East Technical University, Üniversiteler, Eskişehir Yolu No: 1, 06800 Çankaya/Ankara, Turkey
Keywords: carmustine, BCNU, BiCNU, bis-chloroethylnitrosourea, tautomerism, adenine, DFT


Carmustine is a chemotherapic substance used in treatment of various cancers. In the present study, within the constraints of density functional theory (B3LYP/6-31++G(d,p)), tautomerism of carmustine has been investigated. It may undergo 1,3-type proton tautomerism, however the obtained data for vacuum conditions indicated that the equilibrium concentration of the enol type tautomer should be low. Afterwards, interactions of those tautomers with adenine, a constituent base of DNA and RNA, have been investigated. The composites (1:1) are electronically stable. Their heat of formations are exothermic and the free energy of formation values are favorable. Some of their calculated properties (structural, physicochemical and quantum chemical) are obtained and discussed.


J.D. Ahlgren and J.S. Macdonald (Eds.), Gastrointestinal Oncology, Philadelphia: Lippincott Co., 1992.

T.H. Wasserman, M. Slavik and S.K. Carter, Review of CCNU in clinical cancer therapy, Cancer Treatment Reviews 1(2) (1974), 131-151.

C.G. Moertel, Chemotherapy of gastrointestinal cancer, N Engl J Med. 299 (1978), 1049-1052.

J.D. Boice, Jr., M.H. Greene, J.Y. Killen, Jr., S.S. Ellenberg, R.J. Keehn, E. McFadden, T.T. Chen, J.F. Fraumeni, Jr., Leukemia and Preleukemia after Adjuvant Treatment of Gastrointestinal Cancer with Semustine (Methyl-CCNU), N Engl J Med. 309 (1983), 1079-1084.

H.C. Bock, M.J.A. Puchner, F. Lohmann, M. Schütze, S. Koll, R. Ketter, R. Buchalla, N. Rainov, S.R. Kantelhardt, V. Rohde and A. Giese, First-line treatment of malignant glioma with carmustine implants followed by concomitant radiochemotherapy: a multicenter experience, Neurosurg. Rev. 33 (2010), 441-449.

J.K. Aronson (Editor-in-Chief), Nitrosourea cytotoxic drugs, Meyler’s Side Effects of Drugs: The International Encyclopedia of Adverse Drug Reactions and Interactions, 16th ed., Amsterdam: Elsevier, 2016.

A.V. Thatishetty, N. Agresti and C.B. O’Brien, Chemotherapy-Induced Hepatotoxicity, Clinics in Liver Disease 17(4) (2013), 671-686.

J.J.P. Stewart, Optimization of parameters for semiempirical methods I. Method, J. Comput. Chem. 10 (1989), 209-220.

J.J.P. Stewart, Optimization of parameters for semi empirical methods II. Application, J. Comput. Chem. 10 (1989), 221-264.

A.R. Leach, Molecular Modeling, Essex: Longman, 1997.

P. Fletcher, Practical Methods of Optimization, New York: Wiley, 1990.

W. Kohn and L. Sham, Self-consistent equations including exchange and correlation effects, J. Phys. Rev. 140 (1965), 1133-1138.

R.G. Parr and W. Yang, Density Functional Theory of Atoms and Molecules, London: Oxford University Press, 1989.

C.J. Cramer, Essentials of Computational Chemistry, Chichester, West Sussex: Wiley, 2004.

A.D. Becke, Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev. A 38 (1988), 3098-3100.

S.H. Vosko, L. Wilk and M. Nusair, Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis, Can. J. Phys. 58 (1980), 1200-1211.

C. Lee, W. Yang and R.G. Parr, Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density, Phys. Rev. B 37 (1988), 785-789.

SPARTAN 06, Wavefunction Inc., Irvine CA, USA, 2006.

O.Reutov, Theoretical principles of organic chemistry, Moscow: Mir Pub., 1970.

E.V. Anslyn and D.A. Dougherty, Modern Physical Organic Chemistry, Sausalito, California: University Science Books, 2006.

C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 3rd ed., Weinheim: Wiley-VCH, 2003.

Spartan, Molecular Modeling in Physical Chemistry, Irvine, CA, USA: Wavefunction Inc., 2005.

G. Zubay, Biochemistry, Reading: Addison-Wesley, 1983.

How to Cite
Türker, L. (2020). Interaction of Carmustine Tautomers with Adenine - DFT Study. Earthline Journal of Chemical Sciences, 5(1), 63-76.