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