In:
Chemistry – A European Journal, Wiley, Vol. 27, No. 7 ( 2021-02), p. 2427-2438
Abstract:
Artificial nucleic acids are widely used in various technologies, such as nucleic acid therapeutics and DNA nanotechnologies requiring excellent duplex‐forming abilities and enhanced nuclease resistance. 2′‐ O ,4′‐ C ‐Methylene‐bridged nucleic acid/locked nucleic acid (2′,4′‐BNA/LNA) with 1,3‐diaza‐2‐oxophenoxazine (BNAP ( B H )) was previously reported. Herein, a novel B H analogue, 2′,4′‐BNA/LNA with 9‐(2‐aminoethoxy)‐1,3‐diaza‐2‐oxophenoxazine (G‐clamp), named BNAP‐AEO ( B AEO ), was designed. The B AEO nucleoside was successfully synthesized and incorporated into oligodeoxynucleotides (ODNs). ODNs containing B AEO possessed up to 10 4 ‐, 152‐, and 11‐fold higher binding affinities for complementary (c) RNA than those of ODNs containing 2′‐deoxycytidine ( C ), 2′,4′‐BNA/LNA with 5‐methylcytosine ( L ), or 2′‐deoxyribonucleoside with G‐clamp ( P AEO ), respectively. Moreover, duplexes formed by ODN bearing B AEO with cDNA and cRNA were thermally stable, even under molecular crowding conditions induced by the addition of polyethylene glycol. Furthermore, ODN bearing B AEO was more resistant to 3′‐exonuclease than ODNs with phosphorothioate linkages.
Type of Medium:
Online Resource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.202003982
Language:
English
Publisher:
Wiley
Publication Date:
2021
detail.hit.zdb_id:
1478547-X
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