INFLUENCE OF A POSITIVE CHARGE IN THE STRUCTURE OF PHOTOSENSITIZERS OF CHLORIN SERIES ON THE PHOTOINDUCED ANTICANCER ACTIVITY
https://doi.org/10.17650/1726-9784-2015-14-4-87-92
Abstract
A neutral photosensitizer, aminobutylamide chlorin e6 with a terminal amino group (1), and its derivative, a cationic photosensitizer with a terminal trimethylammonium group (2) were synthesized. Spectral, photophysical and photobiological properties of compounds 1 and 2 were studied. An impact of a charge in molecule 2 on a photoinduced antitumor activity was evaluated in vitro. Relative coefficients of intracellular accumulation (Krei) were determined for compounds 1 and 2 in human lung adenocarcinoma A549 and human glioblastoma U251 cells. The coefficients of intracellular accumulation of neutral chlorin 1 in both cell types are fivefold higher than those of cationic chlorin 2. As a consequence, compound 1 surpasses fifteen-fold compound 2 in photoinduced cytotoxicity.
About the Authors
S. S. Brusov
Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov
Russian Federation
Russian Federation
A. V. Efremenko
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences; M.V. Lomonosov Moscow State University
Russian Federation
Russian Federation
V. S. Lebedeva
Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov
Russian Federation
Russian Federation
E. Yu. Shchepelina
Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov
Russian Federation
Russian Federation
Ph. V. Ponomarev
Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov
Russian Federation
Russian Federation
A. V. Feofanov
Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences; M.V. Lomonosov Moscow State University
Russian Federation
Russian Federation
A. F. Mironov
Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov
Russian Federation
Russian Federation
M. A. Grin
Moscow State University of Fine Chemical Technologies named after M.V. Lomonosov
Russian Federation
Russian Federation
References
1. Игнатова А А., Маслова А.С., Кирпичников М.П., Феофанов А.В. Взаимодействия фотосенсибилизатора 13,15-1Ч-(3-гидроксипропил) циклоимида хлорина рб с нормальными и раковыми клетками крови // Биоорг. хим. - 2009. - 35(6) - С. 830-6.
2. Странадко, Е.Ф. Исторический очерк развития фотодинамической терапии // Лазерная медицина. - 2002. - №4. - С. 4-8.
3. Bonnett R. Photodynamic therapy in historical perspective // Rev. Contemp. Pharmacother. - 1999. - 10(1). -P. 1-17.
4. Dougherty T.J., Gomer C.J., Henderson B. W. et al. Photodynamic therapy // J. Natl. Cancer Inst. - 1998. - 90.-P. 889-905.
5. Feofanov A., Grichine A., Karmakova T. et al. Near-infrared photosensitizer based on a cycloimide derivative of chlorin p6: 13,15-N-(3'-hydroxypropyl)cycloimide chlorin p6 // Photochem. Photobiol. - 2002. - 75 -P. 633-43.
6. Grin M.A., Bregadze V.I., Sivaev I.B. et al. Cobalt bis(dicarbollide) versus closo-dodecaborate in boronated chlorin e(6) conjugates: implications for photodynamic and boron-neutron capture therapy // Photochem. Photobiol. Sci. - 2012. - 11 - P. 645-52.
7. Grin M.A., Mironov A.F., Shtil A4. Anti-Cancer Agents // Med. Chem. - 2008. - 8. -P. 683-97.
8. Grin M.A., Refregiers M., Yakubovskaya R.I. et al. Cycloimide bacteriochlorin p derivatives: photodynamic properties and cellular and tissue distribution // Free Radic. Biol. Med. - 2006. - 40. - P. 407-19.
9. Moan J., Peng Q., Iani V et al. Biodistribution, pharmacokinetic and in vivo fluorescence spectroscopic studies of photosensitizers // SPIE - 1995. - 2625. - P. 234-8.
10. Moser J.G. Definitions and General Properties of 2nd and 3rd Generation Photosensitizers // Photodynamic Tumor Therapy - London: Harwood Academic Publishers. - 1997. - P. 3-8.
11. PandeyR.K., Chitgupi U., Lakhminarayanan V.J. Porphyrins Phthalocyanines. - 2012. -16 - P. 1055-8.
12. Pandey R.K., Zheng G. The Porphyrin Handbook / Kadish KM, Smith KM and Guilard R. (Eds.) - Elsevier, 2000.-P. 157-230.
13. Ponomarev G.V., Kaplan M.A., Pospelov V.I. et al. Photosensitizer and its’ Obtaining Method. RF Patent Application. - 2011. - №2416614.
14. Sharma S.K., KrayerM., Sperandio F.F. et al. Porphyrins Phthalocyanines. - 2013. - 73 - P. 17-85.
Review
For citations:
Brusov S.S., Efremenko A.V., Lebedeva V.S., Shchepelina E.Yu., Ponomarev P.V., Feofanov A.V., Mironov A.F., Grin M.A. INFLUENCE OF A POSITIVE CHARGE IN THE STRUCTURE OF PHOTOSENSITIZERS OF CHLORIN SERIES ON THE PHOTOINDUCED ANTICANCER ACTIVITY. Russian Journal of Biotherapy. 2015;14(4):87-92. (In Russ.) https://doi.org/10.17650/1726-9784-2015-14-4-87-92
Views:
431
Email this article 
