Synthesis, properties and in vitro photodynamic activity of water-soluble azaphthalocyanines and azanaphthalocyanines

Photochemistry and Photobiology

Volumn 86, Issue 1, 2010, Pages 168-175

  Zimcik, Petr ^a   Miletin, Miroslav ^a   Radilova, Hana ^b   Novakova, Veronika ^a   Kopecky, Kamil ^a   Svec, Jaroslav ^a   Rudolf, Emil ^c  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b GENERI BIOTECH sro   (Czech Republic)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOCYANINE; INDOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; PHTHALOCYANINE; RADIOSENSITIZING AGENT; WATER;

ARTICLE; CELL LINE; HUMAN; LIGHT; RADIATION EXPOSURE; SOLUBILITY; SYNTHESIS;

CARBOCYANINES; CELL LINE; HUMANS; INDOLES; LIGHT; NAPHTHALENES; RADIATION-SENSITIZING AGENTS; SOLUBILITY; WATER;

TETRA;

EID: 73649113454     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.2009.00647.x     Document Type: Article

References (42)

1. Triesscheijn, M., P. Baas, J. H. M. Schellens F. A. Stewart (2006) Photodynamic therapy in oncology. Oncologist 11, 1034 1044.
2. Zimcik, P. M. Miletin (2009) Photodynamic therapy. In Dyes and Pigments - New Research (Edited by A. R. Lang pp. 1 62. Nova Science Publishers, New York.
3. Castano, A. P., T. N. Demidova M. R. Hamblin (2004) Mechanisms in photodynamic therapy: Part one - Photosensitizers, photochemistry and cellular localization. Photodiagnosis Photodyn. Ther. 1, 279 293.
4. Dougherty, T. J., C. J. Gomer, B. W. Henderson, G. Jori, D. Kessel, M. Korbelik, J. Moan Q. Peng (1998) Photodynamic therapy. J. Natl Cancer Inst. 90, 889 905. (Pubitemid 28304157)
5. Qiang, Y. G., X. P. Zhang, J. Li Z. Huang (2006) Photodynamic therapy for malignant and non-malignant diseases: Clinical investigation and application. Chin. Med. J. 119, 845 857.
6. Moreira, L. M., F. V. dos Santos, J. P. Lyon, M. Maftoum-Costa, C. Pacheco-Soares N. S. da Silva (2008) Photodynamic therapy: Porphyrins and phthalocyanines as photosensitizers. Aust. J. Chem. 61, 741 754.
7. Wainwright, M. (2008) Photodynamic therapy: The development of new photosensitisers. Anti-Cancer Agents Med. Chem. 8, 280 291.
8. Li, H. R., T. J. Jensen, F. R. Fronczek M. G. H. Vicente (2008) Syntheses and properties of a series of cationic water-soluble phthalocyanines. J. Med. Chem. 51, 502 511.
9. Lo, P. C., J. D. Huang, D. Y. Y. Cheng, E. Y. M. Chan, W. P. Fong, W. H. Ko D. K. P. Ng (2004) New amphiphilic silicon(IV) phthalocyanines as efficient photosensitizers for photodynamic therapy: Synthesis, photophysical properties, and in vitro photodynamic activities. Chem. Eur. J. 10, 4831 4838.
10. Amerio, P., T. Gobello, C. Mazzanti, E. Giaculli, S. Ruggeri, D. Sordi, M. Amatetti, L. Chinni A. Tulli (2007) Photodynamic therapy plus topical retinoids in Darier's disease. Photodiagnosis Photodyn. Ther. 4, 36 38.
11. Fabris, C., M. Soncin, G. Miotto, L. Fantetti, G. Chiti, D. Dei, G. Roncucci G. Jori (2006) Zn(II)-phthalocyanines as phototherapeutic agents for cutaneous diseases. Photosensitization of fibroblasts and keratinocytes. J. Photochem. Photobiol. B, Biol. 83, 48 54.
12. Scalise, I. E. N. Durantini (2005) Synthesis, properties, and photodynamic inactivation of Escherichia coli using a cationic and a noncharged Zn(II) pyridyloxyphthalocyanine derivatives. Bioorg. Med. Chem. 13, 3037 3045.
13. Mantareva, V., V. Kussovski, I. Angelov, E. Borisova, L. Avramov, G. Schnurpfeil D. Wöhrle (2007) Photodynamic activity of water-soluble phthalocyanine zinc(II) complexes against pathogenic microorganisms. Bioorg. Med. Chem. 15, 4829 4835.
14. Zhang, Z. B., H. T. Jin, J. Bao, F. Fang, J. F. Wei A. P. Wang (2006) Intravenous repeated-dose toxicity study of ZnPcS2P2-based-photodynamic therapy in Wistar rats. Photochem. Photobiol. Sci. 5, 1006 1017.
15. Farooq, F. T., J. Berlin, E. Baron, A. L. Faulx, J. M. Marks A. Chak (2007) Pilot animal study of the phthalocyanine Pc4 as a topically-applied photosensitizer for PDT of Barrett's esophagus. Gastrointest. Endosc. 65, AB155.
16. Ahmad, N., K. Kalka H. Mukhtar (2001) In vitro and in vivo inhibition of epidermal growth factor receptor-tyrosine kinase pathway by photodynamic therapy. Oncogene 20, 2314 2317.
17. Ke, M. S., L. Y. Xue, D. K. Feyes, K. Azizuddin, E. D. Baron, T. S. McCormick, H. Mukhtar, A. Panneerselvam, M. D. Schluchter, K. D. Cooper, N. L. Oleinick S. R. Stevens (2008) Apoptosis mechanisms related to the increased sensitivity of Jurkat T-cells vs A431 epidermoid cells to photodynamic therapy with the phthalocyanine pc 4. Photochem. Photobiol. 84, 407 414.
18. Sakharov, D. V., E. D. R. Elstak, B. Chernyak K. W. A. Wirtz (2005) Prolonged lipid oxidation after photodynamic treatment. Study with oxidation-sensitive probe C11-BODIPY581/591. FEBS Lett. 579, 1255 1260.
19. Bai, L., J. Guo, F. A. Bontempo J. L. Eiseman (2009) The relationship of phthalocyanine 4 (Pc 4) concentrations measured noninvasively to outcome of Pc 4 photodynamic therapy in mice. Photochem. Photobiol. 85, 1011 1019.
20. Hofman, J. W., F. van Zeeland, S. Turker, H. Talsma, S. A. Lambrechts, D. V. Sakharov, W. E. Hennink C. F. van Nostrum (2007) Peripheral and axial substitution of phthalocyanines with solketal groups: Synthesis and in vitro evaluation for photodynamic therapy. J. Med. Chem. 50, 1485 1494.
21. Zimcik, P., M. Miletin, M. Kostka, J. Schwarz, Z. Musil K. Kopecky (2004) Synthesis and comparison of photodynamic activity of alkylheteroatom substituted azaphthalocyanines. J. Photochem. Photobiol. A, Chem 163, 21 28.
22. Kostka, M., P. Zimcik, M. Miletin, P. Klemera, K. Kopecky Z. Musil (2006) Comparison of aggregation properties and photodynamic activity of phthalocyanines and azaphthalocyanines. J. Photochem. Photobiol. A, Chem 178, 16 25.
23. Mørkved, E. H., N. K. Afseth P. Zimcik (2007) Azaphthalocyanines with extended conjugation through heteroaryl and aryl substituents. Photochemical and photophysical properties. J. Porphyr. Phthalocyanines 11, 130 138.
24. Donzello, M. P., E. Viola, C. Bergami, D. Dini, C. Ercolani, M. Giustini, K. M. Kadish, M. Meneghetti, F. Monacelli, A. Rosa G. Ricciardi (2008) Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 6. Chemical and redox properties and highly effective photosensitizing activity for singlet oxygen production of penta- and monopalladated complexes in dimethylformamide solution. Inorg. Chem. 47, 8757 8766.
25. Kobak, R. Z. U. A. Gül (2009) Synthesis and solution studies on azaphthalocyanines with quaternary aminoethyl substituents. Color. Technol. 125, 22 28.
26. Makhseed, S., F. Ibrahim, C. G. Bezzu N. B. McKeown (2007) The synthesis of metal-free octaazaphthalocyanine derivatives containing bulky phenoxy substituents to prevent self-association. Tetrahedron Lett. 48, 7358 7361.
27. Kudrevich, S. V., M. G. Galpern, E. A. Lukyanets J. E. vanLier (1996) Substituted tetra 2,3-pyrazinoporphyrazines. 1. Angular annelation of tetra-2,3-quinoxalinoporphyrazine. Can. J. Chem. 74, 508 515.
28. Mitzel, F., S. FitzGerald, A. Beeby R. Faust (2003) Acetylenic quinoxalinoporphyrazines as photosensitisers for photodynamic therapy. Chem. Eur. J. 9, 1233 1241.
29. Haas, M., S. X. Liu, A. Neels S. Decurtins (2006) A synthetic approach to asymmetric phthalocyanines with peripheral metal-binding sites. Eur. J. Org. Chem., 2006, 5467 5478.
30. Zimcik, P., M. Miletin, Z. Musil, K. Kopecky, L. Kubza D. Brault (2006) Cationic azaphthalocyanines bearing aliphatic tertiary amino substituents - Synthesis, singlet oxygen production and spectroscopic studies. J. Photochem. Photobiol. A, Chem 183, 59 69.
31. Musil, Z., P. Zimcik, M. Miletin, K. Kopecky J. Lenco (2007) Synthesis, separation and UV/Vis spectroscopy of pyrazino-quinoxalino-porphyrazine macrocycles. Eur. J. Org. Chem., 2007, 4535 4542.
32. Musil, Z., P. Zimcik, M. Miletin, K. Kopecky, M. Link, P. Petrik J. Schwarz (2006) Synthesis and singlet oxygen production of azaphthalocyanines bearing functional derivatives of carboxylic acid. J. Porphyr. Phthalocyanines 10, 122 131.
33. Michelsen, U., H. Kliesch, G. Schnurpfeil, A. K. Sobbi D. Wöhrle (1996) Unsymmetrically substituted benzonaphthoporphyrazines: A new class of cationic photosensitizers for the photodynamic therapy of cancer. Photochem. Photobiol. 64, 694 701.
34. Ogunsipe, A., D. Maree T. Nyokong (2003) Solvent effects on the photochemical and fluorescence properties of zinc phthalocyanine derivatives. J. Mol. Struct. 650, 131 140.
35. Seotsanyana-Mokhosi, I., T. Kresfelder, H. Abrahamse T. Nyokong (2006) The effect of Ge, Si and Sn phthalocyanine photosensitizers on cell proliferation and viability of human oesophageal carcinoma cells. J. Photochem. Photobiol. B-Biol. 83, 55 62.
36. Feofanov, A., A. Grichine, T. Karmakova, N. Kazachkina, E. Pecherskih, R. Yakubovskaya, E. Luyanets, V. Derkacheva, M. Egret-Charlier P. Vigny (2002) Chelation with metal is not essential for antitumor photodynamic activity of sulfonated phthalocyanines. Photochem. Photobiol. 75, 527 533.
37. Youngblood, W. J. (2006) Synthesis of a new trans-A(2)B(2) phthalocyanine motif as a building block for rodlike phthalocyanine polymers. J. Org. Chem. 71, 3345 3356.
38. Kameyama, K., M. Morisue, A. Satake Y. Kobuke (2005) Highly fluorescent self-coordinated phthalocyanine dimers. Angew. Chem. Int. Ed. Engl. 44, 4763 4766.
39. Novakova, V., P. Zimcik, K. Kopecky, M. Miletin, J. Kuneš K. Lang (2008) Self-assembled azaphthalocyanine dimers with higher fluorescence and singlet oxygen quantum yields than the corresponding monomers. Eur. J. Org. Chem. 2008, 3260 3263.
40. Daraio, M. E., A. Völker, P. F. Aramendía E. San Román (1996) Reaction of zinc phthalocyanine excited states with amines in cationic micelles. Langmuir 12, 2932 2938.
41. Block, J. H. J. M. Beale Jr. (2004). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 11th edn. Lippincott Williams & Wilkins, Baltimore.
42. Dummin, H., T. Cernay H. W. Zimmermann (1997) Selective photosensitization of mitochondria in HeLa cells by cationic Zn (II) phthalocyanines with lipophilic side-chains. J. Photochem. Photobiol. B, Biol. 37, 219 229.