| Subject: |
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Physics/Physics/Chemical Physics
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| Title: |
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The 2-aminoglucosamide motif improves cellular uptake and photodynamic activity of tetraphenylporphyrin. |
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| Author(s): |
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Benoit Di Stasio1, 2, Céline Frochot1, Dominique Dumas3, Pascale Even1, Jurriaan Zwier4, Audrey Müller1, Jacques Didelon2, François Guillemin2, Marie-Laure Viriot1, Muriel Barberi-Heyob2 |
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| Laboratory: |
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| Abstract: |
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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. |
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| Fulltext language: |
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English |
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| Publication type: |
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Article in peer-reviewed journal |
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| DOI: |
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10.1016/j.ejmech.2005.04.007 |
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| Journal: |
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| European Journal of Medicinal Chemistry (Eur J Med Chem) |
| Publisher |
Elsevier |
| ISSN |
0223-5234 (eISSN : 1768-3254) |
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| Audience: |
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not specified |
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| Publication date: |
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2005 |
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| Volume: |
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40 |
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| Page, identifiant, ...: |
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1111-1122 |
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| Keyword(s): |
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Photodynamic therapy – Glucosylation – Porphyrin – Chlorin – Targeting – In vitro |
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