Quantitative structure property relationships to evaluate the photosensitizing capability in porphyrins and chlorins

International Journal of Quantum Chemistry

Volumn 111, Issue 7-8, 2011, Pages 1570-1582

  Cárdenas Jirón, Gloria I ^a   Santander Nelli, Mireya ^a   López, Ramón ^b   Menéndez, María Isabel ^b  

^a UNIVERSIDAD DE SANTIAGO DE CHILE   (Chile)

^b UNIVERSITY OF OVIEDO   (Spain)

Author keywords

aromaticity; chlorine; porphyrin; Q band; QSPR

Indexed keywords

AROMATICITIES; CHLORINS; DESCRIPTORS; MULTI-DIMENSIONAL PARAMETERS; PORPHYRIN DERIVATIVES; POTENTIAL CAPABILITY; Q BAND; Q BANDS; QSPR; QSPR MODEL; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS; REGRESSION COEFFICIENT; TIME DEPENDENT;

AROMATIZATION; CHLORINE; DENSITY FUNCTIONAL THEORY; PHOTODYNAMIC THERAPY;

PORPHYRINS;

EID: 79953251623     PISSN: 00207608     EISSN: 1097461X     Source Type: Journal    
DOI: 10.1002/qua.22731     Document Type: Article

References (68)

1. Nowis, D.,;, Makowski, M.,;, Stoklosa, T.,;, Legat, M.,;, Issat, T.,;, Golab, J., Acta Biochim Polym 2005, 52, 339.
2. Sternberg, E. D.,;, Dolphin, D., Tetrahedron 1998, 54, 4151.
3. Nyman, E. S.,;, Hynninen, P. H. J., Photochem Photobiol B: Biol 2004, 73, 1.
4. Castano, A. P.,;, Demidova, T. N.,;, Hamblin, M. R., Photodiag Photodyn Ther 2004, 1, 279.
5. Castano, A. P.,;, Demidova, T. N.,;, Hamblin, M. R., Photodiag Photodyn Ther 2005, 2, 1.
6. Castano, A. P.,;, Demidova, T. N.,;, Hamblin, M. R., Photodiag Photodyn Ther 2005, 2, 91.
7. Banfi, S.,;, Caruso, E.,;, Caprioli, S.,;, Mazzagatti, L.,;, Canti, G.,;, Ravizza, R.,;, Gariboldi, M.,;, Montia, E., Bioorg Med Chem 2004, 12, 4853.
8. Pushpan, S. K.,;, Venkatraman, S.,;, Anand, V. G.,;, Sankar, J.,;, Parmeswaran, D.,;, Ganesan, S.,;, Chandrashekar, T. K., Curr Med Chem: Anti-Cancer Agents 2002, 2, 187.
9. Petit, L.,;, Quartarolo, A.,;, Adamo, C.,;, Russo, N., J Phys Chem B 2006, 110, 2398.
10. Sundholm, D., Phys Chem Chem Phys 2000, 2, 2275.
11. Parusel, A. B. J.,;, Grimme, S., J Porphyrins Phthalocyanines 2001, 5, 225.
12. Parusel, A. B. J.,;, Ghosh, A., J Phys Chem A 2000, 104, 2504.
13. Grimme, S.,;, Waletzke, M., J Chem Phys 1999, 111, 5645.
14. Nagashima, U.,;, Takada, T.,;, Ohno, K., J Chem Phys 1986, 85, 4524.
15. Hasegawa, J.,;, Kimura, T.,;, Nakatsuji, H., J Porph Phthaloc 2005, 9, 305.
16. Hashimoto, T.,;, Choe, Y.-K.,;, Nakano, H.,;, Hirao, K., J Phys Chem A 1999, 103, 1894.
17. Mercader, A. G.,;, Duchowicz, P. R.,;, Fernández, F. M.,;, Castro, E. A.,;, Cabrerizo, F. M.,;, Thomas, A. H., J Mol Graph Model 2009, 28, 12.
18. Fayet, G.,;, Joubert, L.,;, Rotureau, P.,;, Adamo, C., Chem Phys Lett 2009, 467, 407.
19. Fayet, G.,;, Rotureaub, P.,;, Joubert, L.,;, Adamo, C., J Hazard Mater 2009, 171, 845.
20. Ioele, G.,;, De Luca, M.,;, Oliverio, F.,;, Ragno, G., Talanta 2009, 79, 1418.
21. Caruso, L.,;, Musumarra, G.,;, Katritzky A. R., Quant Struct Act Relat 1993, 12, 146.
22. Katritzky, A. R.,;, Gordeeva, E. V., J Chem Inf Comput Sci 1993, 33, 835.
23. Karelson, M.,;, Lobanov, V. S.,;, Katritzky, A. R., Chem Rev 1996, 96, 1027.
24. Palma, M.,;, Cárdenas-Jirón, G. I.,;, Menéndez Rodríguez, M. I., J Phys Chem A 2008, 112, 13574.
25. Fukuda, H.,;, Casas, A.,;, Batlle, A., Int J Biochem Cell Biol 2005, 37, 272.
26. Ichikawaa, K.,;, Takeuchia, Y.,;, Yonezawaa, S.,;, Hikitaa, T.,;, Kurohanea, K.,;, Nambab, Y.,;, Oku, N., Cancer Lett 2004, 205, 39.
27. Sailer, R.,;, Strauss, W. S. L.,;, Emmert, H.,;, Stock, K.,;, Steiner, R.,;, Schneckenburger, H., Photochem Photobiol 2000, 71, 460.
28. Sasnouskia, S.,;, Zorinb, V.,;, Khludeyevb, I.,;, D'Hallewina, M. A.,;, Guillemina, F.,;, Bezdetnaya, L., Biochim Biophys Acta 2005, 1725, 394.
29. Chen, J. Y.,;, Mak, N. K.,;, Yow, C. M. N.,;, Fung, M. C.,;, Chiu, L. C.,;, Leung, W. N.,;, Cheung, N. H., Photochem Photobiol 2000, 72, 541.
30. Kobayashi, W.,;, Liu, Q.,;, Nakagawa, H.,;, Sakaki, H.,;, Teh, B. W.,;, Matsumiya, T.,;, Yoshida, H.,;, Imaizumi, T.,;, Satoh, K.,;, Kimura, H., Oral Oncol 2006, 42, 46.
31. Dube, A.,;, Sharma, S.,;, Gupta, P. K., Oral Oncol 2006, 42, 77.
32. Jaguar, version 7.5; Schrodinger, LLC: New York, 2008.
33. Stratmann, R. E.,;, Scuseria, G. E.,;, Frisch, M. J., J Chem Phys 1998, 109, 8218.
34. Bauernschmitt, R.,;, Ahlrichs, R., Chem Phys Lett 1996, 256, 454.
35. Casida, M. E.,;, Jamorski, C.,;, Casida, K. C.,;, Salahub, D. R., J Chem Phys 1998, 108, 4439.
36. Frisch, M. J.,;, Trucks, G. W.,;, Schlegel, H. B.,;, Scuseria, G. E.,;, Robb, M. A.,;, Cheeseman, J. R.,;, Montgomery, J. A., Jr.,;, Vreven, T.,;, Kudin, K. N.,;, Burant, J. C.,;, Millam, J. M.,;, Iyengar, S. S.,;, Tomasi, J.,;, Barone, V., Mennucci, B.,;, Cossi, M.,;, Scalmani, G.,;, Rega, N.,;, Petersson, G. A.,;, Nakatsuji, H.,;, Hada, M.,;, Ehara, M.,;, Toyota, K.,;, Fukuda, R.,;, Hasegawa, J.,;, Ishida, M.,;, Nakajima, T.,;, Honda, Y.,;, Kitao, O.,;, Nakai, H.,;, Klene, M.,;, Li, X.,;, Knox, J. E.,;, Hratchian, H. P.,;, Cross, J. B.,;, Bakken, V.,;, Adamo, C.,;, Jaramillo, J.,;, Gomperts, R.,;, Stratmann, R. E.,;, Yazyev, O.,;, Austin, A. J.,;, Cammi, R.,;, Pomelli, C.,;, Ochterski, J. W.,;, Ayala, P. Y.,;, Morokuma, K.,;, Voth, G. A.,;, Salvador, P.,;, Dannenberg, J. J.,;, Zakrzewski, V. G.,;, Dapprich, S.,;, Daniels, A. D.,;, Strain, M. C.,;, Farkas, O.,;, Malick, D. K.,;, Rabuck, A. D.,;, Raghavachari, K.,;, Foresman, J. B.,;, Ortiz, J. V.,;, Cui, Q.,;, Baboul, A. G.,;, Clifford, S.,;, Cioslowski, J.,;, Stefanov, B. B.,;, Liu, G.,;, Liashenko, A.,;, Piskorz, P.,;, Komaromi, I.,;, Martin, R. L.,;, Fox, D. J.,;, Keith, T.,;, Al-Laham, M. A.,;, Peng, C. Y.,;, Nanayakkara, A.,;, Challacombe, M.,;, Gill, P. M. W.,;, Johnson, B.,;, Chen, W.,;, Wong, M. W.,;, Gonzalez, C.,;, Pople, J. A., Gaussian 03, Revision E. 01; Gaussian, Inc.: Wallingford, CT, 2004.
37. (a), Becke, A. D., Phys Rev A 1998, 38, 3098
38. (b), Lee, C.,;, Yang, W.,;, Parr, R. G., Phys Rev B 1998, 37, 785
39. (c), Miehlich, B.,;, Savin, A.,;, Stoll, H.,;, Preuss, H., Chem Phys Lett 1989, 157, 200.
40. (a), Vosko, S. H.,;, Wilk, L.,;, Nusair, M., Can J Phys 1980, 58, 1200
41. (b), Hohenberg, P.,;, Kohn, W., Phys Rev 1964, 136, B864
42. (c), Kohn, W.,;, Sham, L. J., Phys Rev 1965, 140, A1133
43. (d), Slater, J. C., The Self-Consistent Field for Molecular and Solids, Quantum Theory of Molecular and Solids; McGraw-Hill: New York, 1974; Vol. 4.
44. Schleyer, P. V. R.,;, Maerker, C.,;, Dransfeld, A.,;, Jiao, H.,;, Hommes, N. J. R. V. E., J Am Chem Soc 1996, 118, 6317.
45. Chen, Z.,;, Wannere, C. S.,;, Corminboeuf, C.,;, Puchta, R.,;, Schleyer, P. V. R., Chem Rev 2005, 105, 3842.
46. Wolinski, K.,;, Hilton, J. F.,;, Pulay, P., J Am Chem Soc 1990, 112, 8251.
47. Kruszewski, J.,;, Krygowski, T. M., Tetrahedron Lett 1972, 36, 3839.
48. Krygowski, T. M., J Chem Inf Comput Sci 1993, 33, 70.
49. Katritzky, A. R.,;, Jug, K.,;, Oniciu, D. C., Chem Rev 2001, 101, 1421.
50. Katritzky, A. R.,;, Barczynski, P.,;, Musumarra, G.,;, Pisano, D.,;, Szafran, M., J Am Chem Soc 1989, 111, 7.
51. Katritzky, A. R.,;, Karelson, M.,;, Sild, S.,;, Krygowski, T. M.,;, Jug, K., J Org Chem 1998, 63, 5228.
52. (a), Krygowski, T. M.,;, Cyranski, M. K., Chem Rev 2001, 101, 1385
53. (b), Cyránski, M. K.,;, Krygowski, T. M.,;, Katritzky, A. R.,;, Schleyer, P. V. R., J Org Chem 2002, 67, 1333.
54. (a), Feixas, F.,;, Matito, E.,;, Poater, J.,;, Solà, M., J Phys Chem A 2007, 111, 4513
55. (b), Poater, J,;, García-Cruz, I.,;, Illas, F.,;, Solá, M., Phys Chem Chem Phys 2004, 6, 314.
56. Glendening, E. D.,;, Badenhoop, J. K.,;, Reed, A. E.,;, Carpenter, J. E.,;, Bohmann, J. A.,;, Morales, C. M.,;, Weinhold, F., NBO 5.0; Theoretical Chemistry Institute, University of Wisconsin: Madison, 2001.
57. Parr, R. G.,;, Donnelly, R. A.,;, Levy, M.,;, Palke. W. E., J Chem Phys 1978, 68, 3801.
58. Parr, R. G.,;, Pearson, R. G., J Am Chem Soc 1983, 105, 7512.
59. Parr, R. G.,;, Szentpály, L. V.,;, Liu. S., J Am Chem Soc 1999, 121, 1922.
60. IBM SPSS Statistics 17.0, 1993-2007.
61. Campomanes, P.,;, Menéndez, M. I.,;, Cárdenas-Jirón, G. I.,;, Sordo, T. L., Phys Chem Chem Phys 2007, 9, 5644.
62. Steiner, E.,:, Fowler, P. W., ChemPhysChem 2002, 3, 114.
63. Steiner, E.,;, Fowler, P. W., Org Biomol Chem 2003, 1, 1785.
64. Steiner, E.,;, Fowler, P. W., Org Biomol Chem 2004, 2, 34.
65. Steiner, E.,;, Fowler, P. W., In Advances in Photosynthesis;, Grimm, B., Porra, R., Rudiger, W., Scheer, H., Eds., Springer: The Netherlands, 2006; Vol. 25.
66. Steiner, E.,;, Soncini, A.,;, Fowler, P. W., Org Biomol Chem 2005, 3, 4053.
67. Bhyrappa, P.,;, Arunkumar, C.,;, Varghese, B. J., Porphyrins Phthalocyanines 2007, 11, 795.
68. Zhua, W.,;, Zhaoa, X.,;, Ou, Z.,;, Zhoua, F.,;, Wanga, X.,;, Kadish, K. M. J., Porphyrins Phthalocyanines 2009, 13, 1233.