title: The 2-aminoglucosamide motif improves cellular uptake and photodynamic activity of tetraphenylporphyrin.
abstract: Several strategies have been proposed to improve the efficiency of photosensitizers used in photodynamic therapy (PDT). In this context, the synthesis of mono- (1) and di-glucosylated (2) porphyrins, and mono-glucosylated chlorin (3) was performed. HT29 human adenocarcinoma cells were significantly more sensitive to asymmetric and less hydrophobic glucosylated photosensitizers-mediated PDT (1, 3), compared to tetraphenylporphyrin (TPP). The lowest photosensitivity observed for TPP was consistent with the lowest uptake. Moreover, the most pronounced photodynamic activity measured for 3 was in relation with the improvement of cellular uptake, the singlet oxygen quantum yield and the high extinction coefficient value at 650 nm compared to porphyrins. Cellular localization analysis showed that 1 and 3 accumulated mainly inside the endoplasmic reticulum.
authors.affiliation: DCPR-GRAPP, UMR 7630 CNRS-INPL, Groupe ENSIC, 1, rue Grandville, 54000 Nancy, France.
authors.forename: Benoît
authors.initials: B
authors.lastname: Di Stasio
authors.forename: Céline
authors.initials: C
authors.lastname: Frochot
authors.forename: Dominique
authors.initials: D
authors.lastname: Dumas
authors.forename: Pascale
authors.initials: P
authors.lastname: Even
authors.forename: Jurriaan
authors.initials: J
authors.lastname: Zwier
authors.forename: Audrey
authors.initials: A
authors.lastname: Müller
authors.forename: Jacques
authors.initials: J
authors.lastname: Didelon
authors.forename: François
authors.initials: F
authors.lastname: Guillemin
authors.forename: Marie-Laure
authors.initials: ML
authors.lastname: Viriot
authors.forename: Muriel
authors.initials: M
authors.lastname: Barberi-Heyob
mesh_terms: D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D019073:HT29 Cells; D006801:Humans; D007700:Kinetics; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis; D017319:Photosensitizing Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011166:Porphyrins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013050:Spectrometry, Fluorescence; D013997:Time Factors
chemical_list: C507734:5,15-bis(4-(1,3,4,6-tetra-O-acetyl-2-amido-2-desoxy-beta-D-glucopyranose phenyl))-10,20-biphenyl porphyrin; C507733:5-(4-(1,3,4,6-tetra-O-acetyl-2-amido-2-desoxy-beta-D-glucopyranose phenyl))-10,15,20-triphenyl chlorin; C507731:5-(4-(1,3,4,6-tetra-O-acetyl-2-amido-2-desoxy-beta-D-glucopyranose phenyl))-10,15,20-triphenyl porphyrin; D009005:Monosaccharides; D017319:Photosensitizing Agents; D011166:Porphyrins; C409084:tetraphenylporphyrin; C006969:chlorin