Structures and electronic absorption spectra of a recently synthesised class of photodynamic therapy agents

Chemistry - A European Journal

Volumn 12, Issue 26, 2006, Pages 6797-6803

  Quartarolo, Angelo Domenico ^a   Russo, Nino ^a   Sicilia, Emilia ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Density functional calculations; Dipyrromethenes; Photodynamic therapy; Solvent effects; Substituent effects

Indexed keywords

DENSITY FUNCTIONAL CALCULATIONS; DIPYRROMETHENES; SOLVENT EFFECTS; SUBSTITUENT EFFECTS;

ELECTRONIC STRUCTURE; LIGHT ABSORPTION; LIGHT POLARIZATION; PHOTODYNAMIC THERAPY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BORON COMPOUNDS;

BORON DERIVATIVE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; PHOTOSENSITIZING AGENT; PORPHOBILINOGEN; PORPHYRIN; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; METHODOLOGY; PHOTOCHEMOTHERAPY; THERMODYNAMICS;

AZA COMPOUNDS; BORON COMPOUNDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; PORPHOBILINOGEN; PORPHYRINS; PYRROLES; THERMODYNAMICS;

EID: 33748537374     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501636     Document Type: Article

References (35)

1. I. J. MacDonald, T. J. Dougherty, J. Porphyrins Phthalocyanines 2001, 5, 105-129.
2. Y. Van Tenten, H. J. Schuitmaker, A. De Wolf, B. Willekens, G. F. J. M. Vrensen, M. J. Tassignon, Exp. Eye Res. 2001, 72, 41-48.
3. D. E. J. G. J. Dolmans, D. Fukumura, R. K. Jain, Nat. Rev. Cancer 2003, 3, 380.
4. T. J. Dougherty, C. J. Gomer, B. W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan, Q. Peng, J. Natl. Cancer Inst. 1998, 90, 889.
5. R. Bonnett, Chem. Soc. Rev. 1995, 24, 19.
6. D. Wöhrle, A. Hirth, T. Bogdahn-Rai, G. Schnurpfeil, M. Shopova, Chem. Bull. 1998, 47, 807.
7. W. M. Sharman, G. M. Allen, J. E. VanLier, Drug Discovery Today 1999, 4, 507.
8. T. S. Mang, R. Allison, G. Hewson, W. Snider, R. Moskowitz, Cancer J. Sci. Am. 1998, 4, 378.
9. S. W. Young, K. W. Woodbourn, M. Wright, Photochem. Photobiol. 1996, 63, 892-897.
10. K. J. Mellish, R. D. Cox, D. I. Vernon, J. Griffiths, S. B. Brown, Photochem. Photobiol. 2002, 75, 392.
11. M. R. Detty, P. B. Merkel, J. Am. Chem. Soc. 1990, 112, 3845.
12. L. M. Williamson, R. Cardigan, C. V. Prowse, Transfusion 2003, 43, 1322.
13. A. Gorman, J. Killoran, C. O'Shea, T. Kenna, W. M. Gallagher, F. D. O'Shea, J. Am. Chem. Soc. 2004, 126, 10619-10631.
14. J. Killoran, L. Allen, J. F. Gallagher, W. M. Gallagher, D. F. O'Shea, Chem. Commun. 2002, 1862-1863.
15. M. Petersilka, U. J. Grossmann, E. K. U. Gross, Phys. Rev. Lett. 1996, 76, 1212.
16. Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
17. M. Ernzerhof, G. E. Scuseria, J. Chem. Phys. 1999, 110, 5029.
18. C. Adamo, V. Barone, J. Chem. Phys. 1999, 110, 6158.
19. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1996, 77, 3865.
20. A. Schaefer, H. Horn, R. Ahlrichs, J. Chem. Phys. 1992, 97, 2571.
21. A. Schaefer, C. Huber, R. Ahlrichs, J. Chem. Phys. 1994, 100, 5829.
22. M. E. Casida in Recent Advances in Density Functional Methods, Part I (Ed.: D. P. Chong), World Scientific, Singapore, 1995.
23. R. E. Stratmann, G. E. Scuseria, M. J. Frisch, J. Chem. Phys. 1998, 109, 8218.
24. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454.
25. P. C. Hariharan, J. A. Pople, Theor. Chim. Acta 1973, 28, 213.
26. P. M. W. Gill, B. G. Johnson, J. A. Pople, M. J. Frisch, Chem. Phys. Lett. 1992, 197, 499.
27. I. Ciofini, C. Daul, C. Adamo, J. Phys. Chem. A 2003, 107, 11182.
28. I. Ciofini, P. P. Lainé, F. Bedioui, C. Adamo, J. Am. Chem. Soc. 2004, 126, 10763.
29. L. Petit, C. Adamo, N. Russo, J. Phys. Chem. B 2005, 109, 12214-12221.
30. R. E. Stratmann, G. E. Scuseria, J. Chem. Phys. 1998, 109, 8218.
31. R. Bauernschmitt, R. Ahlrichs, Chem. Phys. Lett. 1996, 256, 454.
32. D. Jacquemin, J. Preat, V. Wathelet, M. Fontaine, E. A. Perpete, J. Am. Chem. Soc. 2006, 128, 2072.
33. J. Tomasi, M. Persico, Chem. Rev. 1994, 94, 2027.
34. V. Barone, M. Cossi, J. Phys. Chtm. A 1998, 102, 1995.
35. M. Cossi, V. Barone, J. Chem. Phys. 2001, 115, 4708.