Article (Scientific journals)
Semisynthesis and in Vitro Photodynamic Activity Evaluations of Halogenated and Glycosylated Derivatives of Pheophorbide a
Cieckiewicz, Ewa; Mathieu, Véronique; Angenot, Luc et al.
2015In European Journal of Organic Chemistry, 2015 (27), p. 6061-6074
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Keywords :
Photosensitizers; Pheophorbide a; Halogenation; Glycosylation; Photodynamic activity; Photochemistry; Cytotoxicity; Cancer
Abstract :
[en] 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.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Cieckiewicz, Ewa ;  Université de Liège > Département de pharmacie > Pharmacognosie
Mathieu, Véronique
Angenot, Luc  ;  Université de Liège > Département de pharmacie > Département de pharmacie
Gras, Thierry
Dejaegher, Bieke
De Tullio, Pascal ;  Université de Liège > Département de pharmacie > Chimie pharmaceutique
Pirotte, Bernard ;  Université de Liège > Département de pharmacie > Chimie pharmaceutique
Frederich, Michel  ;  Université de Liège - ULiège
Language :
English
Title :
Semisynthesis and in Vitro Photodynamic Activity Evaluations of Halogenated and Glycosylated Derivatives of Pheophorbide a
Publication date :
2015
Journal title :
European Journal of Organic Chemistry
ISSN :
1434-193X
eISSN :
1099-0690
Publisher :
WILEY-VCH Verlag
Volume :
2015
Issue :
27
Pages :
6061-6074
Peer reviewed :
Peer Reviewed verified by ORBi
Available on ORBi :
since 13 October 2015

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