The alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent for improved selectivity to the cytosine base in RNA.

Yosuke Taniguchi, Yusuke Kurose, Takamasa Nishioka, Fumi Nagatsugi, Shigeki Sasaki

Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan.

Bioorganic & medicinal chemistry 2010 Apr 15

filter terms:

We have previously reported that the 2-amino-6-vinylpurine (AVP) nucleoside exhibits a highly efficient and selective crosslinking reaction toward cytosine and displayed an improved antisense inhibition in cultured cells. In this study, we further investigated the alkyl-connected AVP nucleoside analogs for more efficient crosslinking to the cytosine base (rC) of the target RNA. We synthesized three AVP analogs which connect the 2-amino-6-vinylpurine unit to the 2'-deoxyribose through a methylene, an ethylene, or a butylene linker. The ODN incorporating the AVP analog with the methylene or the butylene linker showed a slightly higher crosslinking to the target rC of RNA than the original AVP with no linker. In contrast, the AVP with the ethylene linker formed a selective and efficient crosslink to the rC of the target RNA. Copyright 2010 Elsevier Ltd. All rights reserved.

Citation

Yosuke Taniguchi, Yusuke Kurose, Takamasa Nishioka, Fumi Nagatsugi, Shigeki Sasaki. The alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent for improved selectivity to the cytosine base in RNA. Bioorganic & medicinal chemistry. 2010 Apr 15;18(8):2894-901