GET_pdf delibra

Volume 3 (1) 1997, 55-62


Roszak S., Rzepiela A.

Institute of Physical and Theoretical Chemistry
Wroclaw University of Technology
Wyb. Wyspiańskiego 27
50-370 Wrocław, Poland

DOI:   10.12921/cmst.1997.03.01.55-62



Theoretical studies based on Hartree-Fock (HF) and Density Functional
Theory (with the hybrid functional B3LYP) methods using a 6-31G basis set were
used for (-)cocaine derivatives. Mulliken charges and proton affinities of selected
atoms have been computed at the DFT level of theory for structures of molecules
optimized at the HF level. The unequivocal relations have been found between proton
a f f i n i t i e s and available experimental data. The existence of at least two binding sites
between active cocaine derivatives and the dopamine transporter has been confirmed.


1. F. I. Carroll, A. H. Levin, J. W. Boja and M. J. Kuhar, J. Med. Chem. 35, 969
2. M. J. Kuchar, M. C. Ritz and J. W. Boja, Trends in Neuroscience 14, 299 (1991).
3. F. I. Carroll, A. H. Levin, P. Abraham, K. Parham, J. W. Boja and M. J. Kuhar, J.
Med. Chem. 34, 883 (1991).
4. M. E. A. Reith, B. E. Meisler, H. Sershen and A. Lajtha, Biochem. Pharmacol. 35,
1123 (1986).
5. M. C. Ritz, E. J. Cone and M. J. Cone, Life Sci. 46, 635 (1990).
6. F. I. Carroll, Y. Gao, M. A. Rahman, P. Abraham, K. Parham, A.H. Levin, J. W.
Boja and M. J. Kuhar, J. Med. Chem. 34, 2719 (1991).
7. P. Abraham, J. B. Pitner, A. H. Levin, J. W. Boja, M. J. Kuhar and F. I. Carroll, J.
Med. Chem. 35, 141 (1992).
8. A. H. Lewin, Y. Gao, P. Abracham, J. W. Boja, M. J. Kuhar and F. I. Carroll, J.
Med. Chem. 35, 135 (1992).
9. A. P. Kozikowski, M. Roberti, L. Xiang, J. S. Bergmann, P. M. Callahan, K. A.
Cunningham and K. M. Johnson, J. Med. Chem. 35, 4764 (1994).
10. G. S. Schuelke, L. C. Terry, R. H. Powers, J. Rice and J. A. Madden, Pharm.
Biochem. Behavior 53, 133 (1966).
11. H. M. Deutsch, Q. Shi, E. Gruszecka-Kowalik and M. M. Schweri, J. Med.
Chem. 39, 1201 (1996).
12. A. E. Fleckenstein, T. A. Kopajtic, J. W. Boja, F. I. Carroll and M. J. Kuhar, Eur.
J. Pharmacol. 311, 109 (1996).
13. R. Ditchfield, W. J. Hehre and J. A. Pople, J. Chem. Phys. 54, 724 (1971).
14. R. J. Hrynchuk, R. J. Barton and B. E. Robertson, Can. J. Chem. 61, 481 (1983).
15. M. C. Ritz, E. J. Cone and M. J. Kuchar, Life Sei. 46, 635 (1990).
16. A. D. Becke, J. Chem. Phys. 98, 5648 (1993).
17. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B37, 785 (1988).
18. Materials of ,,7lh International Conference on the Applications of the Density
Functional Theory in Chemistry and Physics”, Technical University, Vienna,
19. Gaussian 94, Revision C.2, M. J. Frish, G. W. Trucks, H. B. Schlegel, P. M. W.
Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, M.
A. Robb, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V.G.
Zakrzewski, J. V. Oritz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A.
Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong,
J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley,
D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J.A.
Pople, Gaussian Inc., Pittsburgh, PA, 1995.