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• W2052568963 abstract "A lactose moiety was regioselectively introduced at various positions of N-hexyl-mesopurpurinimide (a class of chlorin containing a fused six-membered imide ring system, λmax: 700 nm) to investigate the effect of its presence and position on photosensitizing efficacy. The resulting novel structures produced a significant difference in in vitro and in vivo efficacy. Among the positional isomers in which the lactose moiety was introduced at positions 3, 8, and 12, the 3-lactose purpurin-18-N-hexylimide produced the best efficacy. Compared to these analogues, the lactose moiety joined with an amide bond at position 172, and with an N-benzyl group bearing a −C⋮C− linkage at position 132 showed reduced in vitro/in vivo photosensitivity. A noticeable difference between lactose conjugates in cell uptake (RIF tumor cells) was observed at 3 and 24 h postincubation. Replacing the lactose (Galβ1 → 4Glc) with β-galactose and glucose moieties at position 3 of purpurinimide produced an increase in both cell uptake and in in vitro efficacy, but with reduced in vivo efficacy. Sites of intracellular localization differed among photosensitizers with and without carbohydrate moieties. Molecular modeling shows favorable interactions of 3- and 12-lactose-purpurinimide analogues with both galectin-1 and galectin-3, but clear contributions were not found for the conjugate containing lactose moiety at position 8. In a comparative ELISA study of the lactose conjugates with free lactose, all carbohydrate-purpurinimides showed binding to both galectins with a significant variation between the batches of galectins. Keywords: Photosensitizer (PS); carbohydrate; localization; phototoxicity; molecular modeling; photodynamic therapy (PDT)" @default.
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• W2052568963 date "2007-03-21" @default.
• W2052568963 modified "2023-09-26" @default.
• W2052568963 title "Purpurinimide Carbohydrate Conjugates: Effect of the Position of the Carbohydrate Moiety in Photosensitizing Efficacy" @default.
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• W2052568963 doi "https://doi.org/10.1021/mp060135x" @default.
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