Photosensitizers Based on Bacteriopurpurinimide Derivatives and Silica Nanoparticles: Synthesis and Photophysical Properties

Mikhail A. Grin,^a Ivan V. Pantiushenko,^a Anton V. Lobanov,^b,c@ Igor A. Mikhaylov,^c Nataliya B. Sultimova,^d Petr P. Levin,^d Petr V. Ostroverkhov,^a Alexander G. Majouga,^e,f Mikhail Ya. Melnikov,^e and Andrey F. Mironov^a

^aMoscow Technological University, 119571 Moscow, Russia

^bSemenov Institute of Chemical Physics, Russian Academy of Sciences, 119334 Moscow, Russia

^cPlekhanov Russian University of Economics, 117997 Moscow, Russia

^dEmanuel Institute of Biochemical Physics, Russian Academy of Sciences, 119334 Moscow, Russia

^eLomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia

^fNational University of Science and Technology MISiS, 119991 Moscow, Russia

^@Corresponding author E-mail: avlobanov@mail.ru

DOI: 10.6060/mhc160420l

Macroheterocycles 2017 10(3) 273-278

We report the synthesis and optical characterization of photosensitizers related to bacteriopurpurin-N-propoximide and its derivative substituted with aminoethylamide surface attachment group, and their conjugates with silica nanoparticles. The obtained supramolecular complexes are characterized by long-wavelength fluorescence band and the ability to photogeneration of long-lived triplet states with high quantum yield.

References:

Click here to expand or collapse this section

1. Bonnett R. Rev. Contemp. Pharmacother 1999, 10, 1–17.

2. Mironov A.F. Russian Chemical Journal 1998, 42, 23–36.

3. Henderson B.W., Gollnick S.O. In: Biomedical Photonics Handbook (Tuan-Vo-Dinh, Ed.), Boca Raton: CRC Press, 2002. pp. 978-1004

4. Ronn A.M. Rev. Contemp. Pharmacother 1999, 10, 39–46.

5. Freitas I. J. Photochem. Photobiol. 1990, 7, 359–361.
https://doi.org/10.1016/1011-1344(90)85169-W

6. Mason M.D. Rev. Contemp. Pharmacother 1999, 10, 25–37.

7. Moser J.G. Photodynamic Tumor Therapy: 2nd and 3rd Generation Photosensitizers. Amsterdam: Harwood Academic Publishers, 1997, p. 3–8.

8. Grin M.A., Mironov A.F., Shtil A.A. Anti-Cancer Agents in Medicinal Chemistry 2008, 8, 683–697.
https://doi.org/10.2174/187152008785133128

9. Grin M.A., Mironov A.F. Synthetic and Natural Bacteriochlorins. In: Chemical Processes with Participation of Biological and Related Compounds. Biophysical and Chemical Aspects of Porphyrins, Pigments, Drugs, Biodegradable Polymers and Nanofibers (Zaikov G.E., Ed.) Leiden-Boston: CRC Press, 2008. p. 5–43.

10. Koudinova N.V., Pinthus J.H., Brandis A., Brenner O., Bendel P., Ramon J., Eshhar Z., Scherz A., Salomon Y. Int. J. Cancer 2003, 104, 782–789.
https://doi.org/10.1002/ijc.11002

11. Brandis A., Mazor O., Neumark E., Rozenbach-Belkin V., Salomon Y., Scherz A. Photochem. Photobiol. 2009, 81, 983–993.
https://doi.org/10.1111/j.1751-1097.2005.tb01473.x

12. Piao Y., Burns A., Kim J., Wiesner U., Hyeon T. Adv. Funct. Mater. 2008, 18, 3745–3758.
https://doi.org/10.1002/adfm.200800731

13. Kim S., Ohulchanskyy T.Y., Pudavar H.E., Pandey R.K., Prasad P.N. J. Am. Chem. Soc. 2007, 129, 2669–2675.
https://doi.org/10.1021/ja0680257

14. Baba K., Pudavar H.E., Roy I., Ohulchanskyy T.Y., Chen Y., Pandey R.K., Prasad P.N. Mol. Pharmaceutics 2007, 4, 289–297.
https://doi.org/10.1021/mp060117f

15. Ohulchanskyy T.Y., Roy I., Goswami L.N., Chen Y., Bergey E.J., Pandey R.K., Oseroff A.R., Prasad P.N. Nano Lett. 2007, 7, 2835–2842.
https://doi.org/10.1021/nl0714637

16. Chissov V.I., Yakubovskaya R.I., Mironov A.F., Grin M.A., Plotnikova E.A., Morozova N.B., Tsygankov A.A. RF Patent 2521327, 2012.

17. Sul'timova N.B., Levin P.P., Lobanov A.V., Muzafarov A.M. High Energ. Chem. 2013, 47, 98–102.
https://doi.org/10.1134/S0018143913030119

18. Udartseva O.O., Lobanov A.V., Andreeva E.R., Dmitrieva G.S., Melnikov M.Ya., Buravkova L.B. Biophysics 2014, 59, 856–862.
https://doi.org/10.1134/S0006350914060244

19. Scatchard G. Ann. N. Y. Acad. Sci. 1949, 51, 660–672.
https://doi.org/10.1111/j.1749-6632.1949.tb27297.x

20. Stöber W., Fink A., Bohn E. J. Colloid Interface Sci. 1968, 26, 62–69.
https://doi.org/10.1016/0021-9797(68)90272-5

21. Wöhrle D., Buck T., Schneider G., Schulz-Ekloff G., Fisher H. J. Inorg. Metallorg. Polym. 1991, 1, 115–130.
https://doi.org/10.1007/BF00701033

22. Chatterjee S.R., Srivastava T.S. J. Porphyrins Phthalocyanines 2000, 4, 147–157.
https://doi.org/10.1002/(SICI)1099-1409(200003)4:2<147::AID-JPP163>3.0.CO;2-Z

23. Sauer K., Smith J.R.L., Shultz A.J. J. Am. Chem. Soc. 1966, 88, 2681–2688.
https://doi.org/10.1021/ja00964a011

24. Golovina G.V., Novikov F.N., Ol'shevskaya V.A., Kalinin V.N., Shtil A.A., Kuzmin V.A. Russ. J. Phys. Chem. A 2012, 86, 1756–1758.
https://doi.org/10.1134/S003602441211012X

25. Zenkevich E.I., von Borczyskowski C. J. Porphyrins Phthalocyanines 2014, 18, 1–19.
https://doi.org/10.1142/S1088424613300097

26. Krasnovsky A.A., Jr. Photochem. Photobiol. 1979, 29, 29–36.
https://doi.org/10.1111/j.1751-1097.1979.tb09255.x

27. Krasnovsky A.A., Jr. Proc. R. Soc. Edinb. Biol. 1994, 102B, 219–235.

https://doi.org/10.1017/S0269727000014147

Attachment	Size
mhc160420l.pdf	768.76 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Photosensitizers Based on Bacteriopurpurinimide Derivatives and Silica Nanoparticles: Synthesis and Photophysical Properties

References: