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Bioorg Med Chem. 2013 Oct 15;21(20):6124-31. doi: 10.1016/j.bmc.2013.04.058. Epub 2013 Apr 30.

Small molecular inhibitors of miR-1 identified from photocycloadducts of acetylenes with 2-methoxy-1,4-naphthalenequinone.

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1
School of Life Science, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, PR China.

Abstract

Small molecules which can modulate endogenous microRNAs are important chemical tools to study microRNA regulational network. In this Letter we screened the [2+2] photocycloadducts of 2-methoxy-1,4-naphthalenequinone with a series of aryl acetylenes on their activity to modulate endogenous microRNAs. A potent inhibitor of the muscle-specific miR-1 which is closely related with cardiac development and disease was identified. The small molecular inhibitor was the cyclobutene type product derived from the photocycloaddition of 2-methoxy-1,4-naphthalenequinone with tert-butyl (5-(phenylethynyl)quinolin-8-yl) carbonate. Analogues of the small molecular inhibitor were then prepared using similar photocycloaddition reactions for evaluation on inhibition activity on miR-1 to provide structure-activity relationship of the miR-1 inhibitor.

KEYWORDS:

2-Methoxy-1,4-naphthalenequinone; Acetylene; Cyclobutene; Inhibitor of miR-1; Photocycloaddition

PMID:
23685176
DOI:
10.1016/j.bmc.2013.04.058
[Indexed for MEDLINE]
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