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New Сhlorin-Terpene Conjugates: Synthesis, Photoinduced and Dark Cytotoxicity

M. V. Mal’shakova,a Y. I. Pylina,b L. L. Frolova,a J. H. Alekseev,a S. A. Patov,a D. M. Shadrin,b A. V. Kuchin,a I. O. Velegzhaninov,b and D. V. Belykha@


aInstitute of Сhemistry of the Komi Science Centre, Ural Division of Russian Academy of Sciences, 167982 Syktyvkar, Russia

bInstitute of Biology of the Komi Science Centre, Ural Division of Russian Academy of Sciences, 167982 Syktyvkar, Russia

@Corresponding author E-mail:,


DOI: 10.6060/mhc160753b
Macroheterocycles 2016 9(3) 238-243


Based on methylpheophorbide a, the number of chlorin-terpene conjugates containing myrtenyl, camphenyl, cyclobutane and cyclopropane fragments was obtained for the first time with 52–64% yields. Dark and photoinduced cytotoxic activity of the new conjugates was analyzed in comparison with methylpheophorbide a and terpenophenolic chlorin analogue in which terpene fragment was substituted by methyl group. The new compounds were also compared with Photolon, which is currently used in clinical practice. The results show that acetylated aminochlorin, and its conjugates with cis-pinonic and cis-pinononic acids and with 2,2-dimethyl-3-(2-oxopropyl)cyclopropyl acetic acid were characterized by enhanced dark cytotoxicity in comparison with methylpheophorbide a. At the same time, conjugation of aminochlorin with myrtenic or 3,3-dimethylbicyclo[2.2.1]heptane-2-carboxylic acids did not lead to the increase of dark cytotoxicity. The concentrations, at which chlorin-myrtenic (3) and chlorin-camphenylanic (4) conjugates exhibit photoinduced cytotoxicity, differ by more than two orders of magnitude from the concentrations at which these compounds show dark cytotoxicity. In comparison, the difference between the active concentrations under the light and in-the-dark for Photolon is approximately one order of magnitude. This allows to suggest a high potential of the new compounds 3 and 4 for further in vitro and in vivo studies to eventually improve the efficiency and safety of photodynamic therapy of cancer.


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