Chemically robust fluoroalkyl phthalocyanine–oligonucleotide bioconjugates and their GRP78 oncogene photocleavage activity

Abstract

The first representative of functionalized fluoroalkyl phthalocyanines, F₄₈H₇(COOH)PcZn, is reported. The complex generates ¹O₂ affording long-lasting photooxidation of an external substrate without self-decomposition. The carboxylic group couples with an antisense oligonucleotide targeting GRP78 oncogenes, resulting in the F₄₈H₇PcZn–cancer targeting oligonucleotide (CTO). The bioconjugated fluorophthalocyanine effectively hybridizes complementary GRP78 DNA and mRNA sequences. Piperidine cleavage assays reveal desired photochemical oligonucleotide oxidative degradation for both F₄₈H₇PcZn–CTO:DNA and F₄₈H₇PcZn–CTO:mRNA hybrids. This new materials strategy could be extended to other functional fluorinated phthalocyanines–antisense oligonucleotide combinations for long-lasting oncogene-targeting photodynamic therapy.