İlker ÜN, Yunus ZORLU, Hanife İBİŞOĞLU, Fabienne DUMOULIN

A phthalocyanine--fluorescein conjugate

A phthalocyanine--fluorescein conjugate was designed and prepared. Its photophysical properties (electronic absorption and fluorescence) were determined and compared with those of an analogous derivative functionalized by a simple triazole without chromophore. It is likely to be used as a theranostic agent in photodynamic therapy.

Anahtar Kelimeler:

Phthalocyanine, fluorescein, electronic absorption, fluorescence, theranostic agent, third-generation photosensitizer

A phthalocyanine--fluorescein conjugate

Keywords:

Phthalocyanine, fluorescein, electronic absorption, fluorescence, theranostic agent, third-generation photosensitizer,

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Kelkar, S. S.; Reineke, T. M. Bioconjugate Chem. 2011, 22, 1879–1903.
Manthe, R. L.; Foy, S. P.; Krishnamurthy, N.; Sharma, B.; Labhasetwar, V. Mol. Pharm. 2010, 7, 1880–1898.
Stasinopoulos, I.; Penet, M. F.; Chen, Z.; Kakkad, S.; Glunde, K.; Bhujwalla, Z. M. NMR Biomed. 2011, 24, 636–647.
Paterlini-Br´ echot, P. Futur. Oncol. 2011, 7, 849–871.
Lammers, T.; Kiessling, F.; Hennink, W. E.; Storm, G. Mol. Pharm. 2010, 7, 1899–1912.
Ho, Y.-P.; Leong, K. W. Nanoscale 2010, 2, 60–68.
Pan, D.; Caruthers, S. D.; Chen, J.; Winter, P. M.; Senpan, A.; Schmieder, A. H.; Wickline, S. A.; Lanza, G. M. Future Med. Chem. 2010, 2, 471–490.
Garcia-Bennett, A. E. Nanomed. 2011, 6, 867–877.
(a) Pandey, R. K. J. Porphyr. Phthalocya. 2000, 4, 368–373; (b) Macdonald, I. J.; Dougherty, T. J. J. Porphyr. Phthalocya. 2001, 5, 105–129; (c) Josefsen, L. B.; Boyle, R. W. Met.-Based Drugs 2008, 1–24; (d) Ali, H.; van Lier, J. E. Chem. Rev. 1999, 99, 2379–2450.
(a) Hudson, R.; Boyle, R. W. J. Porphyr. Phthalocya. 2004, 8, 954–975; (b) Taquet, J.-P.; Frochot, C.; Manneville, V.; Barberi-Heyob, M. Curr. Med. Chem. 2007, 14, 1673–1687; (c) Bugaj, A. M. Photochem. Photobiol. Sci. 2011, 10, 1097–1109; (d) Bullous, A. J.; Alonso, C. M. A.; Boyle, R. W. Photochem. Photobiol. Sci. 2011, 10, 721–750. (a) Makarov, S.; Litwinski, C.; Ermilov, E. A.; Suvorova, O.; R¨ oder, B.; W¨ ohrle, D. Chem. Eur. J. 2006, 12, 1468–1474; (b) Kobayashi, N.; Furuyama, T.; Satoh, K. J. Am. Chem. Soc. 2011, 133, 19642–19645; (c) K¨ o¸ c, M.; G¨ urek, A. G.; Dumoulin, F.; Ahsen, V. Turk. J. Chem. 2012, 36, 493–502.
Garcia, J.; Gonzalez, A.; Gouloumis, A.; Maya, E. M.; Perez, M. D.; Rey, B. D.; Vazquez, P.; Torres, T. Turk. J. Chem. 1998, 22, 23–31.
(a) Guillaud, G.; Simon, J.; Germain, J. P. Coord. Chem. Rev. 1998, 178–180, 1433–1484; (b) Zhou R.; Josse F.; G¨ opel, W.; ¨ Ozt¨ urk, Z. Z.; Bekaro˘ glu, ¨ O. Applied Organomet. Chem. 1996, 10, 557–577; (c) Rodriguez-M´ endez, M. L.; Gaya, M.; Antonio de Saja, J. J. Porphyr. Phthalocya. 2009, 13, 1159–1167.
(a) Simonneaux, G.; Tagliatesta, P. J. Porphyr. Phthalocya. 2004, 8, 1166–1171; (b) Zagal, J. H.; Griveau, S.; Silva, J. F.; Nyokong, T.; Bedioui, F. Coord. Chem. Rev. 2010, 254, 2755–2791; (c) ˙I¸sci, ¨ U.; Afanasiev, P.; Millet, J.-M. M.; Kudrik, E. V.; Ahsen, V.; Sorokin, A. B. Dalton Trans. 2009, 7410–7420.
Bressan, M.; d’Alessandro, N.; Liberatore, L.; Morvillo, A. Coord. Chem. Rev. 1999, 385, 185–186.
(a) Ayhan, M. M.; Singh, A.; Hirel, C.; G¨ urek, A. G.; Ahsen, V.; Jeanneau, E.; Ledoux-Rak, I.; Zyss, J.; Andraud, C.; Bretonni` ere, Y. J. Am. Chem. Soc. 2012, 8, 3655–3658; (b) Dini, D.; Barthel, M.; Hanack, M. Eur. J. Org. Chem. 2001, 3759–3769; (c) de la Torre, G.; V´ azquez, P.; Agull´ o-L´ opez, F.; Torres, T. Chem. Rev. 2004, 104, 3723–3750.
Dumoulin, F.; Durmu¸s, M. In Photosensitizers in Medicine, Environment, and Security ; Nyokong, T.; Ahsen, V., Eds; Springer, New York, 2012.
Dumoulin, F.; Durmu¸s, M.; Ahsen, V.; Nyokong, T. Coord. Chem. Rev. 2010, 254, 2792–2847.
(a) Pashkovskaya, A.; Kotova, E.; Zorlu, Y.; Dumoulin, F.; Ahsen, V.; Agapov, I.; Antonenko, Y. Langmuir 2010, 26, 5726–5733; (b) Zorlu, Y.; Ermeydan, M. A; Dumoulin, F.; Ahsen, V.; Savoie, H.; Boyle, R. W. Photochem. Photobiol. Sci. 2009, 8, 312–318; (c) Giuntini, F.; Dumoulin, F.; Daly, R.; Ahsen, V.; Scanlan, E. M.; Lavado, A.; Aylott, J. W.; Rosser, G.; Beeby, A.; Boyle, R. W. Nanoscale 2012, 4, 2034–2045.
(a) Zorlu, Y.; Dumoulin, F.; Bouchu, D.; Ahsen V.; Lafont, D. Tetrahedron Lett. 2010, 51, 6615–6618; (b) Lafont, D.; Zorlu, Y.; Savoie, H.; Albrieux, F.; Ahsen, V.; Boyle, R. W.; Dumoulin, F. Photodiag. Photodyn. Ther., 2013, in press http://dx.doi.org/10.1016/j.pdpdt.2012.1.
(a) Dumoulin, F.; Ali, H.; Ahsen, V.; van Lier, J. E. Tetrahedron Lett. 2011, 52, 4395–4397; (b) Ermeydan, M. A.; Dumoulin, F.; Basova, T. V.; Bouchu, D.; G¨ urek, A. G.; Ahsen, V.; Lafont, D. New. J. Chem. 2010, 34, 1153–1162. Zorlu, Y.; Dumoulin, F.; Durmu¸s, M.; Ahsen, V. Tetrahedron 2010, 66, 3248–3258.
Thielbeer, F. Synlett 2012, 23, 1703–1704
Seo, T. S.; Li, Z.; Ruparel, H.; Ju, J. J. Org. Chem. 2003, 68, 609–612.
Tanaka, K.; Kitamura, N.; Chujo, Y. Bioconjugate Chem. 2011, 22, 1484–1490.
Kim, H. N.; Swamy, K. M. K.; Yoon, J. Tetrahedron Lett. 2011, 52, 2340–2343.
Kele, P.; Li X.; Link, M.; Nagy, K.; Herner, A.; L˝ orincz, K.; B´ eni, S.; Wolfbeis, O. S. Org. Biomol. Chem. 2009, 7, 3486–3490.
(a) Kopecky, K.; Novakova, V.; Miletin, M.; Kuˇ cera, R.; Zimcik, P.; Tetrahedron 2011, 67, 5956–5963; (b) Kopecky, K.; Novakova, V.; Miletin, M.; Kuˇ cera, R.; Zimcik, P. Bioconjugate Chem. 2010, 21, 1872–1879.
(a) Dumoulin, F.; Ahsen, V. J. Porphyr. Phthalocya. 2011, 15, 481–504; (b) Yılmaz, Y.; S ¸ener, M. K.; Erden, ˙I.; Avcıata, U. Polyhedron 2009, 28, 3419–3424.
Daugaard, A. E.; Hvilsted, S.; Hansen, T. S.; Larsen, N. B.; Macromolecules 2008, 41, 4321–4327.
Kamino, S.; Kawamae, Y.; Ijyuin, M.; Takada, S.; Yamaguchi, T.; Doi, M.; Fujita, Y. Chem. Pharm. Bull. 2009, 57, 1405–1408.
Cook, A.; Le, A. J. Phys. Chem. Lab 2006, 10, 44–49. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7–13.
Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst. 2006, 39, 453–457.
Bruker, SADABS, Bruker AXS Inc., Madison, Wisconsin, USA, 2005.
Sheldrick, G. M. Acta Cryst. 2008, A64, 112–122.