Synthesis and Optical Properties of Fluorine-Containing Phthalocyanine Conjugated with Glucofuranose and its Application to Photo-Dynamic Therapy

Galactose-conjugated fluorinated and non-fluorinated proline oligomers that exhibit an α-helical structure with hydrophilic and lipophilic parts were designed as potential antifreeze molecules. These galactose-proline oligomers were synthesized and their physical properties were evaluated. Interestingly, the non-fluorinated galactose-proline oligomers showed in contrast to the fluorinated analogues weak antifreeze activity. The difference in antifreeze activity should be attributed to the fluorine gauche effect, which should induce a conformation in fluorinated prolines that is different from that of natural proline. The results obtained in this study thus suggest that the 3D conformation of the galactose-conjugated fluorinated and non-fluorinated proline oligomers is very important for their anti-freezing properties.

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Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

Sumii

Hibino

Saidalimu

et al. 2018

Chem. Commun.

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Broad photodynamic antibacterial activity of a functionalized, highly fluorinated sensitizer

Okorie,

Yussof,

Chu

et al. 2023

J. Porphyrins Phthalocyanines

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Acquired resistance allows bacteria to survive antibiotics, a major health problem. Antibacterial photodynamic inactivation (PDI) relies on photoproduction by a photosensitizer of difficult-to-counteract reactive oxygen species (ROS). We report that a -COOH- functionalized fluoroalkyl-rich fluoro zinc phthalocyanine containing 48 F atoms, is soluble and stable in 99:1% H2O:DMF, and produces 1O2 in quantum yields exceeding 0.30. The photosensitizer induces 93.70–97.28% inhibition of Gram-negative E. coli and P. aeruginosa, and Gram-positive B. subtilis and S. aureus. Such durable, functionalized photosensitizers, exhibiting both inert C-F bonds and reactive-COOH groups, unlike perfluorinated phthalocyanines might be advantageous for constructing covalently bonded new materials with long-term bacterial inactivation activity, useful in a variety of operating environments.

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Synthesis and Optical Properties of Fluorine-Containing Phthalocyanine Conjugated with Glucofuranose and its Application to Photo-Dynamic Therapy

Cited by 2 publications

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Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

Broad photodynamic antibacterial activity of a functionalized, highly fluorinated sensitizer

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