Amino-functionalized water-soluble zinc phthalocyanines: Synthesis,photophysical, photochemical and protein binding properties

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 266, Issue , 2013, Pages 37-46

  Göksel, Meltem ^a   Durmus, Mahmut ^a   Atill, Devrim ^a  

^a GEBZE TECHNICAL UNIVERSITY   (Turkey)

Author keywords

Amino functionalized; Photochemical; Photophysical; Photosensitizer; Phthalocyanine; Singlet oxygen; Zinc

Indexed keywords

EID: 84879474537     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2013.05.017     Document Type: Article

References (32)

1. M. Sbrian-Vazquez, J. Ortiz, I.V.N. Fernández-Lázaro, A. Sastre-Santos, S.A. Soper, M.G.H. Vicente, Synthesis and properties of cell targetedZn(II)-phthalocyanine-peptide conjugates, Bioconjugate Chemistry 18 (2007)410-420. (Pubitemid 46493512)
2. E. Ben-Hur, W.-S. Chan, Phthalocyanines in photobiology and their medicalapplications, in: K.M. Kadish, K.M. Smith, R. Guilard (Eds.), The Porphyrin Hand-book, 19, Academic Press, Boston, 2003, pp. 1-35.
3. M.R. Detty, S.L. Gibson, S.J. Wagner, Current clinical and preclinical photosen-sitizers for use in photodynamic therapy, Journal of Medicinal Chemistry 47(2004) 3897-3915. (Pubitemid 38970949)
4. S. Tuncel, F. Dumoulin, J. Gailer, M. Sooriyaarachchi, D. Atilla, M. Durmuş, D. Bouchu, H. Savoie, R.W. Boyle, V. Ahsen, A set of highly water-solubletetraethyleneglycol-substituted Zn(II) phthalocyanines: synthesis, photo-chemical and photophysical properties, interaction with plasma proteins andin vitro phototoxicity, Dalton Transactions 34 (2007) 3782-3791.
5. I. Okura, Photosensitization of Porphyrins and Phthalocyanines, Gordon andBreach Science Publishers, Kodansha, Tokyo, 2000.
6. F. Dumoulin, M. Durmuş, V. Ahsen, T. Nyokong, Synthetic pathways to water-soluble phthalocyanines and close analogs, Coordination Chemistry Reviews 254 (2010) 2792-2847.
7. H. Ali, J.E. van Lier, Metal complexes as photo- And radiosensitizers, ChemicalReviews 99 (1999) 2379-2450.
8. R. Bonnett, Photosensitizers of the porphyrin and phthalocyanine series forphotodynamic therapy, Chemical Society Reviews 24 (1995) 19-33.
9. T. Nyokong, Desired properties of new phthalocyanines for photodynamic therapy, Pure and Applied Chemistry 83 (2011) 1763-1779.
10. J. Garcia, S. Barluenga, K. Gorska, F. Sasse, N. Winssinger, Synthesis ofdeguelin-biotin conjugates and investigation into deguelin's interactions, Bioorganic and Medicinal Chemistry 20 (2012) 672-680.
11. U. Passcali, M. Cynthia, R.L. Allen, L.M. Carole, E.V.L. Johan, Low-densitylipoprotein-bound aluminum sulfophthalocyanine: Targeting tumor cells forphotodynamic therapy, Journal of Porphyrins and Phthalocyanines 5 (2001)154-161.
12. R. Ion, The use of phthalocyanines and related complexes in photodynamictherapy, in: T. Nyokong, V. Ahsen (Eds.), Photosensitizers in Medicine, Envi-ronment, and Security, Springer, New York, 2012, pp. 315-349.
13. H. Li, T.J. Jensen, F.R. Fronczek, M.G.H. Vicente, Syntheses and properties of aseries of cationic water-soluble phthalocyanines, Journal of Medicinal Chemistry 51 (2008) 502-511. (Pubitemid 351252278)
14. D. Atilla, N. Saydan, M. Durmuş, A.G. Gürek, T. Khan, A. Rück, H. Walt, T. Nyokong, V. Ahsen, Synthesis and photodynamic potential of tetra- Andocta-triethyleneoxysulfonyl substituted zinc phthalocyanines, Journal of Pho-tochemistry and Photobiology A 186 (2007) 298-307.
15. N. Umezawa, N. Matsumoto, S. Iwama, T. Higuchi, Facile synthesis ofpeptide-porphyrin conjugates: Towards artificial catalase, Bioorganic andMedicinal Chemistry 18 (2010) 6340-6350.
16. M.M. Ayhan, G.A. Özpinar, M. Durmuş, T. Clark, A.G. Gürek, The effects of thesubstituents position (a or b) and nature of linker heteroatom (O or S) on thephotophysicochemical properties and theoretical approach for protonation vsaggregation of zinc phthalocyanines, Dalton Transactions (2013) (submittedfor publication).
17. S. Fukuzum, K. Ohkubo, J. Ortiz, A.M. Guierrez, F. Fernandez-Lazaro, A. Sastre-Santos, Control of photoinduced electron transfer in zincphthalocyanine- perylenediimide dyad and triad by the magnesium ion, Journal of Physical Chemistry A 112 (2008) 10744-10752.
18. P. Yiru, H. Fenghua, L. Zhipeng, C. Naisheng, H. Jinling, Synthesis andcharacterization of an unsymmetrical diimide-disulfonato phthalocyanina- tozinc dipotassium salt, Inorganic Chemistry Communications 7 (2004)967-970.
19. A.K. Burat, A. Koca, J.P. Lewtak, D.T. Gryko, Preparation, electrochemistryand optical properties of unsymmetrical phthalocyanines bearing mor-pholine and tert-butylphenoxy substituents, Synthetic Metals 161 (2011)1537-1545.
20. D. de la Torre, C.G. Claessens, T. Torres, Phthalocyanines: The need for selec-tive synthetic approaches, European Journal of Organic Chemistry 16 (2000)2821-2830.
21. N. Kobayashi, M. Togashi, T. Osa, K. Ishii, S. Yamauchi, H. Hino, Supermolecules, Journal of the American Chemical Society 118 (1996) 1073-1085.
22. M.J. Stillman, T. Nyokong, in: C.C. Leznoff, A.B.P. Lever (Eds.), Phthalocya-nines: Properties and Applications, vol. 1, VCH Publishers, New York, 1989(Chapter 3).
23. C. Uslan, B.S. Sesalan, M. Durmuş, Synthesis of new water soluble phthalocya-nines and investigation of their photochemical, photophysical and biologicalproperties, Journal of Photochemistry and Photobiology A: Chemistry 235(2012) 56-64.
24. Z. Biyikliǒglu, M. Durmuş, H. Kantekin, Tetra-2-[2-(dimethylamino)ethoxy]ethoxy substituted zinc phthalocyanines and their quaternizedanaloques: synthesis, characterization, photophysical and photochemicalproperties, Journal of Photochemistry and Photobiology A: Chemistry 222(2011) 87-96.
25. M. Çamur, V. Ahsen, M. Durmuş, The first comparison of photophysical andphotochemical properties of non-ionic, ionic and zwitterionic gallium (III) andindium (III) phthalocyanines, Journal of Photochemistry and Photobiology A:Chemistry 219 (2011) 217-227.
26. S.L. Murov, I. Carmichael, G.L. Hug, Handbook of Photochemistry, second ed., Marcel Decker, New York, 1993.
27. S.M.T. Nunes, F.S. Sguilla, A.C. Tedesco, Photophysical studies of zinc phthalo-cyanine and chloroaluminum phthalocyanine incorporated into liposomes inthe presence of additives, Brazilian Journal of Medical and Biological Research 37 (2004) 273-284. (Pubitemid 38268161)
28. A. Ogunsipe, J-Y. Chen, T. Nyokong, Photophysical and photochemical studies ofzinc(II) phthalocyanine derivatives-effects of substituents and solvents, NewJournal of Chemistry 28 (2004) 822-827. (Pubitemid 39108020)
29. M. Durmuş, Photochemical and photophysical characterization, in: T. Nyokong, V. Ahsen (Eds.), Photosensitizers in Medicine, Environment, and Security, Springer, New York, 2012, pp. 135-267.
30. T. Nyokong, Effects of substituents on the photochemical and photophysical properties of main group metal phthalocyanines, Coordination ChemistryReviews 251 (2007) 1707-1722.
31. I. Gürol, M. Durmuş, V. Ahsen, T. Nyokong, Synthesis, photophysical and photo-chemical properties of substituted zinc phthalocyanines, Dalton Transactions 34 (2007) 3782-3791. (Pubitemid 47294581)
32. N. Kuznetsova, N. Gretsova, E. Kalmkova, E. Makarova, S. Dashkevich, V. Neg-rimovskii, O. Kaliya, E. Luk'yanets, Relationship between the photochemicalproperties and structure of pophyrins and related compounds, Russian Journalof General Chemistry 70 (2000) 133-140.