A phthalaldehyde-substituted phthalocyanine has been synthesized that can conjugate with a range of biomolecules, including peptides, monosaccharides, lipids, and DNAs, and be immobilized on the surface of bovine serum album nanoparticles and glass slides using the versatile and efficient phthalaldehyde-amine capture reactions. The light-induced cytotoxic effects of the latter two materials have also been examined against cancer cells and bacteria, respectively, showing that they are highly efficient photosensitizing systems for photodynamic therapy.
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Specific Activation of Photosensitizer with Extrinsic Enzyme for Precisive Photodynamic Therapy.
J Am Chem Soc
June 2022
Department of Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China.
Delivery of functional proteins into the intracellular space has been a challenging task that could lead to a myriad of therapeutic applications. We report herein a novel bioconjugation strategy for enzyme modification and selective delivery into cancer cells for lock-and-key-type activation of photosensitizers. Using a bifunctional linker containing a bis(bromomethyl)phenyl group and an -phthalaldehyde moiety, it could induce cyclization of the peptide sequence Ac-NH-CRGDfC-CONH through site-specific dibenzylation with the two cysteine residues and further coupling with β-galactosidase via the phthalaldehyde-amine capture reaction.
View Article and Find Full Text PDFPhthalaldehyde-Amine Capture Reactions for Bioconjugation and Immobilization of Phthalocyanines.
Org Lett
September 2020
Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China.
A phthalaldehyde-substituted phthalocyanine has been synthesized that can conjugate with a range of biomolecules, including peptides, monosaccharides, lipids, and DNAs, and be immobilized on the surface of bovine serum album nanoparticles and glass slides using the versatile and efficient phthalaldehyde-amine capture reactions. The light-induced cytotoxic effects of the latter two materials have also been examined against cancer cells and bacteria, respectively, showing that they are highly efficient photosensitizing systems for photodynamic therapy.
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