Dual fluorescence of ellipticine: Excited state proton transfer from solvent versus solvent mediated intramolecular proton transfer

Journal of Physical Chemistry A

Volumn 115, Issue 33, 2011, Pages 9217-9225

  Banerjee, Sanghamitra ^a   Pabbathi, Ashok ^a   Sekhar, M Chandra ^a   Samanta, Anunay ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLIC SOLVENTS; DIFFERENT SOLVENTS; DUAL FLUORESCENCE; ELLIPTICINE; EMISSION BANDS; EXCITED STATE REACTIONS; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; EXCITED-STATE PROTON TRANSFER; EXPERIMENTAL DATA; GROUND AND EXCITED STATE CALCULATION; INTRAMOLECULAR PROTON TRANSFER; LONG-WAVELENGTH EMISSIONS; NATURAL PLANTS; PHOTOPHYSICAL PROPERTIES; PROTONATED; PYRIDINE NITROGEN; STEADY STATE; TAUTOMERIC FORMS; TIME-RESOLVED FLUORESCENCE;

DENSITY FUNCTIONAL THEORY; ETHYLENE; ETHYLENE GLYCOL; FLUORESCENCE; HYDROGEN; HYDROGEN BONDS; METHANOL; MOLECULES; NITROGEN COMPOUNDS; ORGANIC SOLVENTS; POLYCYCLIC AROMATIC HYDROCARBONS; PROTON TRANSFER; RATE CONSTANTS; SOLVENTS; YTTERBIUM COMPOUNDS;

EXCITED STATES;

ANTINEOPLASTIC AGENT; ELLIPTICINE; ELLIPTICINE DERIVATIVE; NITROGEN; PROTON; PYRIDINE DERIVATIVE; SOLVENT;

ARTICLE; BRAIN TUMOR; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; FLUORESCENCE; HUMAN; HYDROGEN BOND; SOLUBILITY; SPECTROFLUOROMETRY;

ANTINEOPLASTIC AGENTS; BRAIN NEOPLASMS; ELLIPTICINES; FLUORESCENCE; HUMANS; HYDROGEN BONDING; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR STRUCTURE; NITROGEN; PROTONS; PYRIDINES; SOLUBILITY; SOLVENTS; SPECTROMETRY, FLUORESCENCE;

EID: 80051870205     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp206232b     Document Type: Article

References (49)

1. Garbett, N. C.; Graves, D. E. Curr. Med. Chem. 2004, 4, 149
2. Smith, A. F.; Horning, E. C.; Goodwin, S. J. Am. Chem. Soc. 1959, 81, 1903
3. Le Pecq, J.-B.; Xuong, N.-D.; Gosse, C.; Paoletti, C. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 5078
4. Ohashi, M.; Oki, T. Expert Opin. Ther. Pat. 1996, 6, 1285
5. Woodward., R. B.; Iacobucci., G. A.; Hochstein., F. A. J. Am. Chem. Soc. 1959, 81, 4434
6. Ellies, D.; Rosenberg, W. Ellipticine compounds for treating obesity. PCT Int. Appl. WO 2010107704; 2010, p 1.
7. Hallard, M.; Pontiggia, P.; Mathe, G. Biomed. Pharmacother. 1996, 50, 510
8. Clarysse, A.; Brugarolas, A.; Siegenthaler, P.; Abele, R.; Cavalli, F.; De Jager, R.; Renard, G.; Rozencweig, M.; Hansen, H. H. Eur. J. Cancer Clin. Oncol. 1984, 20, 243
9. Dodion, P.; Rozencweig, M.; Nicaise, C.; Piccart, M.; Cumps, E.; Crespeigne, N.; Kisner, D.; Kenis, Y. Eur. J. Cancer Clin. Oncol. 1982, 18, 519
10. Gouyette, A.; Huertas, D.; Droz, J.-P.; Rouesse, J.; Amiel, J.-L. Eur. J. Cancer Clin. Oncol. 1982, 18, 1285
11. Paoletti, C.; Le Pecq, J. B.; Dat-Xuong, N.; Juret, P.; Garnier, H.; Amiel, J.-L.; Rouesse, J. Recent Res. Cancer Res. 1980, 40, 107
12. Liu, J.; Xiao, Y.; Allen, C. J. Pharm. Sci. 2004, 93, 132
13. Searle, F.; Gac-Breton, S.; Keane, R.; Dimitrijevic, S.; Brocchini, S.; Sauville, E. A.; Duncan, R. Bioconjugate Chem. 2001, 12, 711
14. Trubetskoy, V. S.; Torchilin, V. P. Adv. Drug Delivery Rev. 1995, 16, 311
15. Czerwinski, G.; Tarasova, N. I.; Michejda, C. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 11520
16. Moody, T. W.; Czerwinski, G.; Tarasova, N. I.; Moody, D. L.; Michejda, C. J. Regul. Pept. 2004, 123, 187
17. Moody, T. W.; Czerwinski, G.; Tarasova, N. I.; Michejda, C. J. Life Sci. 2002, 71, 1005
18. Sbai, M.; Lyazidi, S. A.; Lerner, D. A.; del Castillo, B.; Martin, M. A. Anal. Chim. Acta 1995, 303, 47
19. Schwaller, M.-A.; Allard, B. J. Phys. Chem. 1994, 98, 4209
20. Reha, D.; Kabelac, M.; Ryjacek, F.; Sponer, J.; Sponer, J. E.; Elstner, M.; Suhai, S.; Hobza, P. J. Am. Chem. Soc. 2002, 124, 3366
21. Froelich-Ammon, S. J.; Patchan, M. W.; Osheroff, N.; Thompson, R. B. J. Biol. Chem. 1995, 270, 14998
22. El Hage Chahine, J. M.; Bertigny, J.-P.; Schwaller, M.-A. J. Chem. Soc., Perkin Trans. 2 1989, 629
23. Auclair, C. Arch. Biochem. Biophys. 1987, 259, 1
24. Bailly, C.; Ohuigin, C.; Rivalle, C.; Bisagni, E.; Waring, M. J. Nucleic Acids Res 1990, 18, 6283
25. Behravan, G.; Leijon, M.; Selhlstedt, U.; Vallberg, H.; Bergamn, J.; Gra slund, A. Biopolymers 1994, 34, 599
26. Canals, A.; Purciolas, M.; Aymami, J.; Coll, M. Acta Crystallogr. 2005, 61, 1009
27. Dodin, G.; Schwaller, M. A.; Aubard, J.; Paoletti, C. Eur. J. Biochem. 1988, 176, 371
28. Elcock, A. H.; Rodger, A.; Richards, W. G. Biopolymers 1996, 39, 309
29. Jain, S. C.; Bhandary, K. K.; Sobell, H. M. J. Mol. Biol. 1979, 135, 813
30. Kohn, K. W.; Waring, M. J.; Glaubiger, D.; Friedman, A. Cancer Res. 1975, 35, 71
31. Fung, S. Y.; Duhamel, J.; Chen, P. J. Phys. Chem. A 2006, 110, 11446
32. Miskolczy, Z.; Biczók, L.; Jablonkai, I. Chem. Phys. Lett. 2006, 427, 76
33. Sbai, M.; Ait Lyazidi, S.; Lerner, D. A.; del Castillo, B.; Martin, M. A. J. Pharm. Biomed. Anal. 1996, 14, 959
34. Cabo, J. L.; Faria, H. B.; Portuga, S. G. M.; Silva, M. A. A.; Brinn, I. M. Photochem. Photobiol. 1999, 69, 664
35. Itoh, M.; Adachi, T.; Tokumura, K. J. Am. Chem. Soc. 1984, 106, 850
36. Bhattacharya, B.; Samanta, A. J. Phys. Chem. B 2008, 112, 10101
37. Kang, B.; Ko, K. C.; Park, S.-Y.; Jang, D.-J.; Lee, J. Y. Phys. Chem. Chem. Phys. 2011, 13, 6332
38. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals; Pergamon Press: New York, 1980.
39. Paul, A.; Samanta, A. J. Phys. Chem. B 2008, 112, 16626
40. Santhosh, K.; Banerjee, S.; Rangaraj, N.; Samanta, A. J. Phys. Chem. B 2010, 1967
41. Santhosh, K.; Samanta, A. J. Phys. Chem. B 2010, 114, 9195
42. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454
43. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. Rev. B 1998, 108, 4439
44. Cossi, M.; Barone, V. J. Chem. Phys. 2000, 2427
45. Reichardt, C. Chem. Rev 1994, 94, 2319
46. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry; Wiley-VCH: New York, 2004; p 433.
47. Diverdi, L. A.; Topp, M. R. J. Phys. Chem. 1984, 88, 3447
48. Mataga, N.; Tsuno, S. Bull. Chem. Soc. Jpn. 1957, 30, 368
49. Marks, D.; Zhang, H.; Borowicz, P.; Waluk, J.; Glasbeek, M. J. Phys. Chem. A 2000, 104, 7167