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Novel Porphyrazine Derivatives show Promise for Photodynamic Therapy despite Restrictions in Hydrophilicity
Author(s) -
Horne Tamarisk K.,
Cronjé Marianne J.
Publication year - 2014
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/php.12231
Subject(s) - porphyrazine , chemistry , photodynamic therapy , phototoxicity , tetrahydrofuran , solubility , fluorescence , dichloromethane , photochemistry , combinatorial chemistry , nuclear chemistry , solvent , organic chemistry , in vitro , biochemistry , physics , quantum mechanics
Complexing of ligands to photosensitizers (Ps) has gained popularity by enhancing solubility, cell‐surface recognition and tissue specificity for applications in Photodynamic Therapy ( PDT ) and fluorescence‐based diagnostics. Here we report on nine carbohydrate‐functionalized porphyrazine (Pz‐galactopyranose/methyl‐ribose) derivatives bearing either H 2 , Zn( II ) or Ni( II ) cores for potential use in PDT . Derivatives proved soluble only in organic solvents; dichloromethane ( DCM ) and tetrahydrofuran ( THF ). Derivatives were subsequently solubilized using DCM ‐based PEG ‐ DSPE 5000 ‐ PBS encapsulation for biological studies due to THF cytotoxicity. Absorption spectra analyses viewed no correlation between core ion, carbohydrate type and peripheral position though encapsulation efficiency (% EE ) followed a general order of Zn( II ) (60–92%) > H 2 (5–34%) > Ni( II ) (4–21%). As such, phototoxicity of Zn( II )Pz derivatives were far superior to H 2 Pz and Ni( II )Pz counterparts following 631.4 nm excitation of MCF ‐7 breast cancer cells. Variation was attributed to persistent aggregation and low % EE when regarding the absorption properties recorded. It is therefore believed that revision of the encapsulation method for H 2 Pz and Ni( II )Pz derivatives would render improved phototoxicity. Zn( II )Pz derivatives show promise as agents for PDT of cancer.