Influence of the carbohydrate fragment position in the macrocycle of chlorine e6 trimethyl ester glycosylated derivatives on their in vitro photo- induced activity
Abstract
The physicochemical and photophysical properties, as well as photo-induced activity, of glycoconjugates based on chlorine е6 trimethyl ether with various positions of carbohydrate fragment in the macrocycle have been studied. The photo-induced activity was investigated in the human (HEp2, A549 and HT29) and animal (LLC) cell lines. The tested compounds showed in vitro both high photo-induced activity and high stability in the dark. The photosensitizer with galactose in the A pirrole ring demonstrated the highest activity (the half maximal inhibitory concentration (ИК50) varied from 27±2 nM to 75±5 nM in tests on different cell lines). Dyes with sugar substitutes in the C pirrole ring were 5–10 times less active.
About the Authors
R. I. YakubovskayaRussian Federation
A. D. Plyutinskaya
Russian Federation
E. A. Plotnikova
Russian Federation
M. A. Grin
Russian Federation
A. F. Mironov
Russian Federation
V. S. Sergeeva
Russian Federation
References
1. Миронов А.Ф. Фотодинамическая терапия рака – новый эффективный метод диагностики и лечения злокачественных опухолей // Соровский образовательный журнал. – 1996. – № 8. – С. 32–40.
2. Grin M.A., Lonin I.S., Makarov A.I. et all. Synthesis of chlorincarbohydrate conjugates by «click chemistry» // Mendeleev Commun. – 2008. – Vol. 18. – No. 3. – P. 135–137.
3. Zhang M., Zhang Z., Blessington D. et al. Pyropheophorbide 2-deoxyglucosamide: a new photosensitizer targeting glucose transporters // Bioconjugate Chem. – 2003. – V. 14(4). – P. 709–714.
4. Grin M.A., Lonin I.S., Lakhina A.A., Ol’shanskaya E.S. et all. 1,3 – dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins // J. Porphyrins Phthalocyanines. – 2009. – Vol. 13. – P. 336–345.
5. Luksiene Z. Photodynamic therapy: mechanism of action and ways to improve the efficiency of treatment // Medicina. – 2003. – V. 39 (12). – P. 1137–1150.
6. Park Y.K., Bold B., Cui B.C. et al. Binding Affinities of Carbohydrate-Conjugated Chlorins for Galectin-3 // Bull. Korean Chem. Soc. – 2008. – V. 29 (1). – P. 130–134.
7. Bonnett. R., Martinez G. Phitobleaching of sensitisers used in phitodynamic therapy // Tetrahedron. – 2001. – V. 57 (47). – P. 9513–9547.
8. Dougherty T.J., Gomer C.J., Henderson B.W. et al. Photodynamic therapy // J. Natl. Cancer I. – 1998. – V. 90 (12). – P. 889–905.
9. Grin M.A., Lonin I.S., Lakhina A.A., Mironov A.F. Cross-metathesis of olefins in a synthesis of glycoconjugates based on chlorophyll a derivatives // Mendeleev Communication. – 2012. – V. 22. – P. 157–158.
10. Carmichael J., DeGraff W.G., Gazdar A.F. et al. // Cancer Res. – 1987. – Vol. 47. – P. 936–942.
Review
For citations:
Yakubovskaya R.I., Plyutinskaya A.D., Plotnikova E.A., Grin M.A., Mironov A.F., Sergeeva V.S. Influence of the carbohydrate fragment position in the macrocycle of chlorine e6 trimethyl ester glycosylated derivatives on their in vitro photo- induced activity. Photodynamic therapy and photodyagnosis. 2014;3(2):3-7. (In Russ.)