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A Standard Methodology to Examine On-site Mutagenicity As a Function of Point Mutation Repair Catalyzed by CRISPR/Cas9 and SsODN in Human Cells
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Cross-Linking Antisense Oligodeoxyribonucleotides with a Photoresponsive α-Chloroaldehyde Moiety for RNA Point

Yuta Sugihara1, Yuki Nakata1, Asako Yamayoshi2,3

  • 1Department of Biomolecular Engineering, Graduate School of Science and Technology, Kyoto Institute of Technology , Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.

The Journal of Organic Chemistry
|January 21, 2016
PubMed

Insights

Researchers developed novel photo-cross-linking oligodeoxyribonucleotides ((pro)PCA-ODNs) for targeted RNA mutation detection. These reagents efficiently and selectively bind to specific RNA sequences, offering potential for new anticancer therapies.

Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Oligonucleotide Therapeutics

Background:

  • Point mutations in GTPase-coding genes are implicated in cellular transformation.
  • Development of targeted anticancer reagents for specific RNA mutations is crucial.
  • Need for sequence-selective agents that can identify and react with mutated RNA.

Purpose of the Study:

  • To develop novel photo-cross-linking oligodeoxyribonucleotides ((pro)PCA-ODNs).
  • To investigate the reactivity and selectivity of these ODNs with target RNAs.
  • To assess the potential of (pro)PCA-ODNs as anticancer reagents.

Main Methods:

  • Synthesis of (pro)PCA-ODNs with a caged α-chloroaldehyde group on a 2-methylpropanediyl backbone.
  • Kinetic study to determine the deprotection rate of the caged group.
  • Photo-cross-linking experiments with complementary oligoribonucleotides (ORNs).

Main Results:

  • The bis(2-nitrobenzyl)acetal group in (pro)PCA-ODNs showed complete deprotection within 1 minute.
  • (pro)PCA-ODNs demonstrated efficient and sequence-selective photo-cross-linking with target ORNs.
  • Reactivity was observed with ORNs containing adenosine or cytidine at the position adjacent to the mutation site, without affecting nearby bases.

Conclusions:

  • Novel (pro)PCA-ODNs are effective photo-cross-linking agents for targeting specific RNA mutations.
  • These ODNs exhibit high selectivity and efficiency in reacting with mutated RNA sequences.
  • The developed technology shows promise for the development of sequence-selective anticancer reagents.

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