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Semisynthesis and in Vitro Photodynamic Activity Evaluations of Halogenated and Glycosylated Derivatives of Pheophorbide a

par Cieckiewicz, Ewa;Mathieu, Véronique ;Angenot, Luc;Gras, Thierry ;Dejaegher, Bieke ;de Tullio, Pascal;Pirotte, Bernard ;Frédérich, Michel
Référence European Journal of Organic Chemistry, 2015, 27
Publication Publié, 2015-09

Article révisé par les pairs

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Résumé :

The present work focuses on the semisynthesis of halogenated and glycosylated derivatives of pheophorbide a (Pha). Because of the low reaction yields enocuntered en route to halogenated derivatives, we then focused only on the semisynthesis of glycosylated derivatives of Pha with the aim at enhancing the Pha specificity for cancer cells by introducing β-galactose moieties expected to bind gal-1. We applied LC-SPE-NMR/MS, to facilitate the direct identification of glycosylated derivatives. The transposition of these analytical methods to a preparative scale facilitated the isolation of glycosylated compounds in quantities sufficient to evaluate in vitro photodynamic efficacies. The in vitro growth inhibitory activity of semisynthesized compounds was then evaluated using the MTT colorimetric assay in the presence and absence of light. However, this pharmacological evaluation method seems to be unable to efficiently yield information about carbohydrate effects in relation to possible compound specificities for gal-1 overexpressed by B16F10 cancer cells.