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Structural Tailoring of a Novel Fluorescent IRE-1 RNase Inhibitor to Precisely Control Its Activity.

Abstract：

:Activation of the IRE-1/XBP-1 pathway has been linked to many human diseases. We report a novel fluorescent tricyclic chromenone inhibitor, D-F07, in which we incorporated a 9-methoxy group onto the chromenone core to enhance its potency and masked the aldehyde to achieve long-term efficacy. Protection of the aldehyde as a 1,3-dioxane acetal led to strong fluorescence emitted by the coumarin chromophore, enabling D-F07 to be tracked inside the cell. We installed a photolabile structural cage on the hydroxy group of D-F07 to generate PC-D-F07. Such a modification significantly stabilized the 1,3-dioxane acetal protecting group, allowing for specific stimulus-mediated control of inhibitory activity. Upon photoactivation, the re-exposed hydroxy group on D-F07 triggered the aldehyde-protecting 1,3-dioxane acetal to slowly decompose, leading to the inhibition of the RNase activity of IRE-1. Our novel findings will also allow for spatiotemporal control of the inhibitory effect of other salicylaldehyde-based compounds currently in development.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Shao A,Kang CW,Tang CH,Cain CF,Xu Q,Phoumyvong CM,Del Valle JR,Hu CC

doi

10.1021/acs.jmedchem.9b00269

subject

Has Abstract

pub_date

2019-06-13 00:00:00

pages

5404-5413

issue

11

eissn

0022-2623

issn

1520-4804

journal_volume

62

pub_type

杂志文章

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