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Synthesis and properties of cationic derivaties of meso-tetra(4-pyridyl)porphyrin

Abstract

Synthesis of amphyphilic cationic meso-pyridilsubstituted porphyrins bearing long chain alkyl groups is described. An improved methods of preparation of tetra- and mono-alkylsubstituted meso-pyridil porphyrins are proposed. The data porphyrins will be investigated as mesogenic compounds and in studing of DNA-binding interactions of cationic porphyrins.

About the Authors

N. V. Novikov
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation


V. V. Starkov
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation


K. A. Formirovskiy
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation


N. A. Bragina
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation


I. P. Ushakova
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation


A. F. Mironov
МИТХТ им. М.В. Ломоносова, 119571, Москва, пр-т Вернадского, д. 86
Russian Federation


References

1. Chou, J.H. In: Porphyrin Handbook / J.H. Chou. / Ed. K.M. Kadish [et al.] - Amsterdam : Acad. Press, 2000. - Vol. 6. - P. 346-360.

2. A perspective on four new porphyrin-based functional materials and devices / C.M. Drain [et al.] // J. Porphyrins & Phthalocyanines. - 2002. - Vol. 6. - P. 243-258.

3. Пикуз, С.С. Модельные системы на основе липид-порфириновых ансамблей и липо-порфиринов в биохимических исследованиях / С.С. Пикуз, Ю.Л. Себякин // Биоорг. химия. - 1996. - T. 22. - C. 725-736.

4. Hudson, R. Lipophilic cationic porphyrins as photodynamic sensitizers - synthesis and structure-activity relationships / R. Hudson, H. Savoie, R. Boyle // Photodiagn. Photodynam. Therapy. - 2005. - Vol. 2. - P. 193-196.

5. Caminos, D. Photodynamic inactivation of Escherichia coli immobilized on agar surfaces by a tricationic porphyrin / D. Caminos, E. Durantini // Bioorg. Med. Chem. - 2006. - Vol. 14. - P. 4253-4259.

6. Synthesis of cationic β-vinyl substituted meso-tetraphenylporphyrins and their in vitro activity against herpes simplex virus type 1E / E. Silva [et al.] // Bioorg. Med. Chem. Lett. - 2005. - Vol. 15. - P. 3333-3337.

7. Effect of albumin on the photodynamic inactivation of microorganisms by a cationic porphyrin / S. Lambrechts [et al.] // J. Photochem. Photobiol. B. - 2005. - Vol. 79. - P. 51-57.

8. Understanding binding interactions of cationic porphyrins with B-form DNA / D. McMillin [et al.] // Coordination Chem. Rev. - 2005. - № 249. - P. 1451-1459.

9. Irradiated cationic meso-porphyrin induces larger damage to isolated rat liver mitochondria than the anionic form / N. Inada [et al.] // Arch. Biochem. Biophys. - 2007. - № 457. - P. 217-224.

10. Han, F. Interactions of TMPyP4 and TMPyP2 with quadruplex DNA. Structural basis for the differential effects on telomerase inhibition / F. Han, R Wheelhouse, L. Hurley // J. Am. Chem. Soc. - 1999. - Vol. 121. - P. 3561-3566.

11. Banfi, S. Antibacterial activity of tetraaryl-porphyrin photosensitizers: An in vitro study on Gram negative and Gram positive bacteria / S. Banfi, E. Caruso // J. Photochem. Photobiol. B: Biology. - 2006. - Vol. 85. - P. 28-38.

12. Meso-substituted tetra-cationic porphyrins photosensitize the death of human fibrosarcoma cells via lysosomal targeting / F. Ricchelli [et al.] // Int. J. Biochem. & Cell Biol. - 2005. - Vol. 37. - P. 306-319.

13. Binding modes of V(=O)meso-tetrakis(N-methylpyridinium-4-yl)porphyrin to various synthetic DNAs studied by polarized spectroscopy / T.G. Park [et al.] // Biochim. Biophys. Acta. - 2006. - Vol. 1760. - P. 388-394.

14. Synthesis, characterization and photochemistry of 5,10,15,20-tetrakis(4-N-pentyl-pyridil)porphyrins, [(TpePyP)H2]4+ and [(TpePyP)ZnII]4+ / H.M. Ajith Herath [et al.] // J. Porphyrins & Phthalocyanines. - 2005. - Vol. 9. - P. 155-162.

15. Аскаров, К.А. Порфирины: структура, свойства, синтез / К.А. Аскаров, Б.Д. Березин, Р.П. Евстигнеева / Pед. Н.С. Ениколопян. - М. : Наука, 1987. - 384 с.

16. Титце, Л. Препаративная органическая химия / Л. Титце, Т. Айхер. Пер. с нем. - М. : Мир, 1999. - 704 с.

17. Okuno, Y. An improved synthesis of surfactant porphyrins / Y. Okuno, W.E. Ford, M. Calvin // Chem. Commun. - 1980. - Vol. 10. - P. 537-539.


Review

For citations:


Novikov N.V., Starkov V.V., Formirovskiy K.A., Bragina N.A., Ushakova I.P., Mironov A.F. Synthesis and properties of cationic derivaties of meso-tetra(4-pyridyl)porphyrin. Fine Chemical Technologies. 2009;4(4):26-30. (In Russ.)

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ISSN 2410-6593 (Print)
ISSN 2686-7575 (Online)