Document Detail


Benzylidene Acetal Type Bridged Nucleic Acids: Changes in Properties Upon Cleavage of the Bridge Triggered by External Stimuli.
MedLine Citation:
PMID:  21644240     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Four classes of benzylidene acetal type bridged nucleic acids (BA-BNAs) were designed with 2',4'-bridged structures that cleaved upon exposure to appropriate external stimuli. Cleavage of 6-nitroveratrylidene and 2-nitrobenzylidene acetal type BNA bridges occurred upon photoirradiation and subsequent treatment with thiol caused changes in secondary structure to afford 4'-C-hydroxymethyl RNA. Benzylidene and 4-nitrobenzylidene acetal type BNA responded to acids and reducing agents, respectively, resulting in hydrolysis of the acetal-bridged structure. Cleavage of the bridge removed sugar conformational restrictions and changed the duplex- and triplex-forming properties of the BNA-modified oligonucleotides. Moreover, oligonucleotides incorporating a single BA-BNA modification had considerably improved stability toward 3'-exonuclease, which was lost upon cleavage of the bridge. Thus, these new BNAs may be useful as therapeutic and detection tools by sensing various environments.
Authors:
Kunihiko Morihiro; Tetsuya Kodama; Satoshi Obika
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-6-3
Journal Detail:
Title:  Chemistry (Weinheim an der Bergstrasse, Germany)     Volume:  -     ISSN:  1521-3765     ISO Abbreviation:  -     Publication Date:  2011 Jun 
Date Detail:
Created Date:  2011-6-6     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9513783     Medline TA:  Chemistry     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Affiliation:
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8204.
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