Lead structures for applications in photodynamic therapy 7. Efficient synthesis of amphiphilic glycosylated lipid porphyrin derivatives: refining linker conjugation for potential PDT applications

Herein, we report synthetic strategies towards a library of amphiphilic tetraphenyl porphyrins anchored to synthetic saccharides and lipid modalities. The carbohydrates and lipid functionalities are covalently linked to the model photosensitizer via a copper (I) catalyzed alkyne azide cycloaddition...

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Bibliographic Details
Published in:Tetrahedron 2015-06, Vol.71 (24), p.4145-4153
Main Authors: Moylan, Claire, Sweed, Ayman M.K., Shaker, Yasser M., Scanlan, Eoin M., Senge, Mathias O.
Format: Article
Language:English
Subjects:
Amphiphilic
Click chemistry
Glycoporphyrin
Lipid
Photodynamic therapy
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Summary:Herein, we report synthetic strategies towards a library of amphiphilic tetraphenyl porphyrins anchored to synthetic saccharides and lipid modalities. The carbohydrates and lipid functionalities are covalently linked to the model photosensitizer via a copper (I) catalyzed alkyne azide cycloaddition reaction or an oxypropyl linkage achieved by nucleophilic substitution chemistry. Varying substitutions of carbohydrates and lipids allows for potential fine tuning of solubility and photophysical characteristics important for imaging and treatment applications in photomedicine, specifically in photodynamic therapy. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.04.097