In search for materials that can be used in chemotherapy of photodynamic cancer therapy a series N-alkylated and N,N-alkilated 3,5-bis(arylidene)piperidones where
R = NMe2, NEt2, OMe, F, Cl, etc; X = H, Alk or AlkOH; Y = Cl, Br, I has been synthesized. Several representatives of this series were found to be fluorescent, that make them practical to study their distribution in cancer cells. For some of arylinenepiperidones two-photon absorption activity was found under near IR radiation, that makes them potential candidates for application in two-photon photodynamic therapy.
Structural characteristics of arylinenepiperidones have been studied using X-ray diffraction analysis. It was shown that central fragment of the molecule is almost planar with the exception of the N atom, that significantly deviates from a plane. This fragment considered being responsible for a specific binding in the cancer cell.
Dark cytotoxic activity of arylinenepiperidones and cytotoxic activity after irradiation of cell culture with visible light have been evaluated using three cancer cell lines. Influence of donor-acceptor substitution and N-alkilation of arylinenepiperidones will be discussed in relation to their cytotoxicity under different conditions.
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