Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2022, Issue 33, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202200318
Keywords
Antisense agents; Alkylation of RNA; Disulfide bond; Glutathione; Peptide nucleic acids
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Funding
- Projekt DEAL
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Quinone methide precursors protected with alkyldithiomethyl groups have been synthesized and converted into PNA conjugates. These conjugates remain stable without reducing agents, but release electrophilic quinone methide in the presence of glutathione, typical of cytosolic concentrations. Self-alkylation or crosslinking of RNA occurs when hybridized with complementary strands, with the fastest reactions observed for the least hindered compound.
Quinone methide precursors protected with alkyldithiomethyl groups have been synthesized and converted into PNA conjugates. Stable in the absence of reducing agents, the electrophilic quinone methide is released by glutathione in concentrations typical for the cytosol. Self-alkylation then occurs or crosslinking of RNA when hybridized with complementary strands. Fastest reactions are seen for the sterically least hindered compound.
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