UV-vis spectra of the anticancer campothecin family drugs in aqueous solution: Specific spectroscopic signatures unraveled by a combined computational and experimental study

Journal of Physical Chemistry B

Volumn 113, Issue 16, 2009, Pages 5369-5375

  Sanna, Nico ^a   Chillemi, Giovanni ^a   Gontrani, Lorenzo ^a,b   Grandi, Andrea ^a   Mancini, Giordano ^a,c   Castelli, Silvia ^d   Zagotto, Giuseppe ^e   Zazza, Costantino ^a   Barone, Vincenzo ^f,g   Desideri, Alessandro ^d  

^a CASPUR   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSITY OF BARI   (Italy)

^d UNIVERSITY OF ROME TOR VERGATA   (Italy)

^e UNIVERSITY OF PADOVA   (Italy)

^f CNR   (Italy)

^g SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BODY FLUIDS; CHARGE TRAPPING; DENSITY FUNCTIONAL THEORY; DRUG INTERACTIONS; DYNAMICS; MOLECULAR DYNAMICS; MOLECULES; PROBABILITY DENSITY FUNCTION;

AQUEOUS SOLUTIONS; CAMPOTHECIN; CAMPTOTHECIN; DFT COMPUTATIONS; EXPERIMENTAL DATA; EXPERIMENTAL SPECTRA; EXPERIMENTAL STUDIES; EXPLICIT WATER; FORCE FIELDS; MOLECULAR DYNAMICS SIMULATIONS; PERIODIC CONDITIONS; QUANTITATIVE AGREEMENT; SOLVATION PATTERNS; SOLVENT EFFECTS; SPECTROSCOPIC SIGNATURES; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TOPOTECAN; ULTRAVIOLET-VISIBLE ABSORPTION SPECTRUM; UV-VIS SPECTRA; WATER MOLECULE;

ABSORPTION SPECTROSCOPY;

EID: 66349091349     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp809801y     Document Type: Article

References (39)

1. Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888-3890.
2. (a) Bailly, C. Cut. Rev. Oncol. Hematol. 2003, 45, 91-108.
3. (b) Nagoumey, R. A.; Sommers, B. L.; Harper, S. M.; Radecki, S.; Evans, S. S. Br. J. Cancer 2003, 89, 1789-1795.
4. (c) Garcia-Carbonero, R.; Supka, J. G. Clin. Cancer Res. 2002, 8, 641-661.
5. (d) Accessing the European Patent website http://ep.espacenet.com/ using "camptothecin" as a simple search keyword has given, at present time, 1746 hits.
6. (a) Pommier, Y.; Pourquier, P.; Fan, Y.; Strumberg, D. Biochim. Biophys. Ada 1998,1400, 83-106.
7. (b) Pommier, Y.; Redon, C.; Rao, V. A.; Seiler, J. A.; Sordet, O.; Takemura, H.; Antony, S.; Meng, L. H.; Liao, Z. Y.; Kohlhagen, G.; Zhang, H. L.; Kohn, K. W. Mutat. Res. 2003, 532, 173-203.
8. (c) Leppard, J. B.; Champoux, J. J. Chromosoma 2005, 114, 75-85.
9. (a) Staker, B. L.; Hjerrild, K.; Feese, M. D.; Behnke, C. A.; Burgin, A. B.; Stewait, L. Proc. Natl. Acad. Sci. 2002, 99, 15387-15392.
10. (b) Staker, B. L.; Feese, M. D.; Cushman, M.; Pommier, Y.; Zembower, D.; Stewart, L.; Burgin, A. B. J. Med. Chem. 2005, 48, 2336-2345.
11. (c) Chrencik, J. E.; Staker, B. L.; Burgin, A. B.; Pourquier, P.; Pommier, Y.; Stewart, L.; Redinbo, M. R. J. Mol. Biol. 2004, 339, 773-784.
12. (a) Posokhov, Y.; Biner, H.; Icli, S. J. Photochem. Photobiol. A: Chem. 2003, 758, 13-20.
13. (b) Dey, J.; Warner, I. M. J. Photochem. Photobiol. A: Chem. 1996,101, 21-27.
14. (c) Nabiev, I.; Fleury, F.; Kudelina, I.; Pommier, Y.; Charton, F.; Riou, J. F.; Alix, A. J. P.; Manfait, M. Biochem. Pharm. 1998, 55, 1163-1174.
15. (d) Thomas, C. J.; Rahier, N. J.; Hecht, S. M. Bioorg. Med. Chem. 2004, 12, 1585-1604.
16. (e) Du, W. Tetrahedron 2003, 59, 8649-8687.
17. Sanna, N.; Chillemi, G.; Grandi, A.; Castelli, S.; Desideri, A.; Barone, V. J. Am. Chem. Soc. 2005, 127 (44), 15429-15436.
18. Chillemi, G.; Castrignano, T.; Desideri, A. Biophys. J. 2001, 87, 490-500.
19. Chillemi, G.; Fiorani, P.; Benedetti, P.; Desideri, A. Nucleic Acids Res. 2003, 31, 1525-1535.
20. Chillemi, G.; Redinbo, M.; Bruselles, A.; Desideri, A. Biophys. J. 2004, 87, 4087-4097.
21. Chillemi, G.; Bruselles, A.; Fiorani, P.; Bueno, S.; Desideri, A. Nucleic Acids Res. 2007, 35 (9), 3032-8.
22. Zhao, H.; Lee, C.; Sai, P.; Choe, Y. H.; Boro, M.; Pendri, A.; Guan, G.; Greenwald, R. B. J. Org. Chem. 2000, 65, 4601-4606.
23. Frisch, M. J.; et al. Gaussian 03 Rev. C2; Gaussian, Inc.: Wallingford, CT, 2004.
24. (a) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Chem. Phys. 2002, 777, 43-54.
25. (b) Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-678.
26. (c) Improta, R.; Barone, V. J. Am. Chem. Soc. 2004, 126, 14320-14321.
27. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
28. Casida, M. K. In Recent Advances in Density Functional Methods, Part I; World Scientific: Singapore, 1995.
29. Cossi, M.; Barone, V. J. Chem. Phys. 2000, 112, 2427-2435.
30. Cossi, M.; Barone, V. J. Chem. Phys. 2001, 775, 4708-4717.
31. Adamo, C.; Scuseria, G. E.; Barone, V. J. Chem. Phys. 1999, 777, 2889-2899.
32. Jaquemin, A.; Perpete, E. A.; Scuseria, G. E.; Ciofini, I.; Adamo, C. J. Chem. Theory Comput. 2008, 4, 123-135.
33. Case, D. A.; et al. AMBER 8; University of California: San Francisco, 2004.
34. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Kollmann, P. A. J. Am. Chem. Soc. 1993, 775, 9620-9631.
35. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. J. Comput. Chem. 2004, 25, 1157-1174.
36. Van der Spoel, D.; Lindahl, E.; Hess, B.; van Buuren, A. R.; Apol, E.; Meulenhoff, P. J.; Tieleman, D. P.; Sijbers, T. M.; Feenstra, K. A.; van Drunen, R.; Berendsen, H. J. C. Gromacs User Manual Version 3.3; www.gromacs.org, 2005.
37. Crescenzi, O.; Pavone, M.; De Angelis, F.; Barone, V. J. Phys. Chem. 2005, 709, 445-453.
38. E.g., see: Silverstein, S. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, Vth ed.; J. Wiley & Sons: New York, 1991.
39. Bergman, D. L.; Laaksonen, L.; Laaksonen, A. J. Mot Graph. Mod. 1997, 75, 301-306.