TY - JOUR
T1 - The alkyl-connected 2-amino-6-vinylpurine (AVP) crosslinking agent for improved selectivity to the cytosine base in RNA
AU - Taniguchi, Yosuke
AU - Kurose, Yusuke
AU - Nishioka, Takamasa
AU - Nagatsugi, Fumi
AU - Sasaki, Shigeki
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (S) from the Japan Society for Promotion of Science , and CREST from the Japan Science and Technology Agency .
PY - 2010/4/15
Y1 - 2010/4/15
N2 - 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.
AB - 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.
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U2 - 10.1016/j.bmc.2010.03.008
DO - 10.1016/j.bmc.2010.03.008
M3 - Article
C2 - 20346683
AN - SCOPUS:77950517274
SN - 0968-0896
VL - 18
SP - 2894
EP - 2901
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 8
ER -