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Photophysics of Glycosylated Ring‐Fused Chlorin Complexes and Their Photosensitizing Effects on Cancer Cells

Von Wiley-VCH zur Verfügung gestellt

The future of photodynamic therapy (PDT) as a promising cancer treatment relies on development of new selective and effective photosensitizers (PS) with improved photophysical and biochemical qualities. Herein, we present the synthesis procedure, photophysical properties and photosensitizing effects of novel glycosylated 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine] fused chlorins agents featuring either glucose, galactose, and N-acetyl glucosamine. It is shown that both the proto- and Zn2+-ion forms of the ring-stabilized glycochlorins exhibit the required photophysical properties in terms of triplet excited states and singlet oxygen, the latter more than 50% in organic solvents such as CHCl3. Employing the rat AY-27 and human T24 cancer cell models, it was found that these are superior to the corresponding unglycosylated chlorin in biological activity, and moreover, the proto form is 2-3 times superior to the Zn-stabilized variant. Provisional flow cytometry and cell localization studies of the proto-form indicate both necrotic and apoptotic biological activity, and that the photo-sensitizer localizes both in the mitochondria, cell membrane and lysosomes. However, the localization into the latter is dominating and increases substantially with time. We anticipate the findings will aid in the development of photosensitizers for targeted cancer PDT.

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