Synthesis and Evaluation of Oligonucleotide-Containing 2′-O-{[(4,5′,8-Trimethylpsoralen)-4′-ylmethoxy]ethylaminocarb-onyl}adenosine as Photo-crosslinkable Gene Targeting Tools

Yu Mikame; Yui Sakai; Ryo Tahara; Kinuka Doi; Tsuyoshi Yamamoto; Chikara Dohno; Takayuki Shibata; Asako Yamayoshi

doi:10.1248/cpb.c22-00333

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Synthesis and Evaluation of Oligonucleotide-Containing 2′-O-{[(4,5′,8-Trimethylpsoralen)-4′-ylmethoxy]ethylaminocarb-onyl}adenosine as Photo-crosslinkable Gene Targeting Tools

Yu Mikame, Yui Sakai, Ryo Tahara, Kinuka Doi, Tsuyoshi Yamamoto, Chikara Dohno, Takayuki Shibata, Asako Yamayoshi

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Keywords: photoreactive, oligonucleotide, psoralen, preference, antisense

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Supplementary material

2022 Volume 70 Issue 10 Pages 726-730

DOI https://doi.org/10.1248/cpb.c22-00333

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Abstract

Several psoralen-conjugated oligonucleotides (Ps-Oligos) have been developed as photo-crosslinkable oligonucleotides targeting DNA or RNA. To avoid potential off-target effects, it is important to investigate the selective photo-crosslinking reactivity of Ps-Oligos to DNA or RNA. However, the selectivity of these Ps-Oligos has not been reported in detail thus far. In this study, we evaluated the photo-crosslinking properties of two Ps-Oligos, 5′-Ps-Oligo and a novel Ps-Oligo containing 2′-O-{[(4,5′,8-trimethylpsoralen)-4′-ylmethoxy]ethylaminocarbonyl}adenosine (APs2-Oligo). Notably, 5′-Ps-Oligo preferentially crosslinked with DNA, whereas APs2-Oligo preferentially crosslinked with RNA. These results demonstrate the interesting crosslinking properties of Ps-Oligos, which will provide useful information for the molecular design of novel Ps-Oligos in future studies.

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