Transition states of cisplatin bindig to guanine and adenine: Ab initio reactivity study

Collection of Czechoslovak Chemical Communications

Volumn 68, Issue 6, 2003, Pages 1105-1118

  Chval, Zdenek ^a   Šíp, Miroslav ^a  

^a UNIVERSITY OF SOUTH BOHEMIA   (Czech Republic)

Author keywords

Ab initio calculations; Antitumor drugs; Chelates; DFT; DNA; Hydrogen bonds; Nucleobases; Platinum; Purines; Reaction mechanisms; Recognition

Indexed keywords

ADENINE; CISPLATIN; GUANINE;

AB INITIO CALCULATION; ARTICLE; BAY REGION BINDING SITE; CHEMICAL STRUCTURE; DNA ADDUCT; DNA BINDING; DRUG HYDROLYSIS; ENERGY ABSORPTION; HYDROGEN BOND; REACTION ANALYSIS;

EID: 0038142679     PISSN: 00100765     EISSN: None     Source Type: Journal    
DOI: 10.1135/cccc20031105     Document Type: Article

References (35)

1. Eastman A.: Biochemistry 1985, 24, 5027.
2. Fichtinger-Schepman A. M. J., Van der Veer J. L., Den Hartog J. H. J., Lohman P. H. M., Reedijk J.: Biochemistry 1985, 24, 707.
3. Reeder F., Guo Z., Murdoch P. S., Corazza A., Hambley T. W., Berners-Price S. J., Chottard J. C., Sadler P. J.: Eur. J. Biochem. 1997, 249, 370.
4. Gonnet F., Reeder F., Kozelka J., Chottard J. C.: Inorg. Chem. 1996, 35, 1653.
5. Elmroth S. K. C., Lippard S. J.: J. Am. Chem. Soc. 1994, 116, 3633.
6. Gonnet F., Kocher F., Blais J. C., Bolbach G., Tabet J. C., Chottard J. C.: J. Mass Spectrom. 1996, 31, 802.
7. Miller S. E., House D. A.: Inorg. Chim. Acta 1990, 173, 53; and references therein.
8. Berners-Price S. J., Frenkiel T. A., Frey U., Ranford J. D., Sadler P. J.: J. Chem. Soc., Chem. Commun. 1992, 789.
9. Black C. B., Cowan J. A.: J. Am. Chem. Soc. 1994, 116, 1174.
10. Schmidt M. W., Baldridge K. K., Boatz J. A., Elbert S. T., Gordon M. S., Jensen J. J., Koseki S., Matsunaga N., Nguyen K. A., Su S., Windus T. L., Dupuis M., Montgomery J. A.: J. Comput. Chem. 1993, 14, 1347.
11. Frisch M. J., Trucks G. W., Schlegel H. B., Gill P. M. W., Johnson B. G., Robb M. A., Cheeseman J. R., Keith T. A., Petersson G. A., Montgomery J. A., Raghavachari K., Al-Laham M. A., Zakrzewski V. G., Ortiz J. V., Foresman J. B., Peng C. Y., Ayala P. A., Wong M. W., Andres J. L., Replogle E. S., Gomperts R., Martin R. L., Fox D. J., Binkley J. S., Defrees D. J., Baker J., Stewart J. P., Head-Gordon M., Gonzalez C., Pople J. A.: Gaussian 94 (Revision D.4). Gaussian, Inc., Pittsburgh (PA) 1995.
12. Hay P. J., Wadt W. R.: J. Phys. Chem. 1985, 82, 299.
13. Stevens W. J., Krauss M., Basch H., Jasien P. G.: Can. J. Chem. 1992, 70, 612.
14. Pavankumar P. N. V., Seetharamulu P., Yao S., Saxe J. D., Reddy D. G., Hausheer F. H.: J. Comput. Chem. 1999, 20, 365.
15. Chval Z., Šíp M.: J. Mol. Struct. (THEOCHEM) 2000, 532, 59.
16. Irikura K. K., Goddard III, W. A.: J. Am. Chem. Soc. 1994, 116, 8733.
17. Takahara P. M., Frederick C. A., Lippard S. J.: J. Am. Chem. Soc. 1996, 118, 12309.
18. Gelasco A., Lippard S. J.: Biochemistry 1998, 37, 9230.
19. Šponer J., Sabat M., Gorb L., Leszcynski J., Lippert B., Hobza P.: J. Phys. Chem. B: At., Mol. Opt. Phys. 2000, 104, 7535.
20. Pelmenschikov A., Zilberberg I., Leszcynski J., Famulari A., Sironi M., Raimondi M.: Chem. Phys. Lett. 1999, 314, 496.
21. Zilberberg I. L., Avdeev V. I., Zhidomirov G. M.: J. Mol. Struct. (THEOCHEM) 1997, 418, 73.
22. Burda J. V., Zeizinger M., Šponer J., Leszczynski J.: J. Chem. Phys. 2000, 113, 2224.
23. Hobza P., Šponer J.: Chem. Rev. (Washington, D. C.) 1999, 99, 3247.
24. Burda J. V., Šponer J., Leszcynski J.: J. Biol. Inorg. Chem. 2000, 5, 178.
25. Estimated by comparison of structures with only one H-bond: e.g. TSAde1b with TS1a.
26. Deubel D. V.: J. Am. Chem. Soc. 2002, 124, 5834.
27. Deeth R. J., Elding L. I.: Inorg. Chem. 1996, 35, 5019.
28. Pullman A., Pullman B.: Q. Rev. Biophys. 1981, 14, 289.
29. Laoui A., Kozelka J., Chottard J.-C.: Inorg. Chem. 1988, 27, 2751.
30. Reedijk J.: Chem. Commun. 1996, 801.
31. Sullivan S. T., Ciccarese A., Fanizzi F. P., Marzilli L. G.: J. Am. Chem. Soc. 2001, 123, 9345.
32. Berners-Price S. J., Frey U., Ranford J. D., Sadler P. J.: J. Am. Chem. Soc. 1993, 115, 8649.
33. Green M., Garner M., Orton D. H.: Transition Met. Chem. (London) 1992, 17, 164.
34. Bonnacorsi R., Scrocco E., Tomasi J., Pullman A.: Theor. Chim. Acta 1975, 36, 339.
35. 3 hydrogen bonds.