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Mixed alkoxy/hydroxy 1,8-naphthalimides: expanded fluorescence colour palette and in vitro bioactivity

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Abstract

An efficient and functional group tolerant route to access hydroxy 1,8-naphthalimides has been used to synthesise a range of mono- and disubstituted hydroxy-1,8-naphthalimides with fluorescence emissions covering the visible spectrum. The dialkoxy substituted compounds prepared possess high quantum yields (up to 0.95) and long fluorescent lifetimes (up to 14 ns). The method has been used to generate scriptaid analogues that successfully inhibit HDAC6 in vitro with tubulin acetylation assays confirming that these compounds are more effective than tubastatin.

Graphical abstract: Mixed alkoxy/hydroxy 1,8-naphthalimides: expanded fluorescence colour palette and in vitro bioactivity

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Supplementary files

Article information


Submitted
17 Feb 2020
Accepted
28 Apr 2020
First published
29 Apr 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Mixed alkoxy/hydroxy 1,8-naphthalimides: expanded fluorescence colour palette and in vitro bioactivity

E. E. Rudebeck, R. P. Cox, T. D. M. Bell, R. Acharya, Z. Feng, N. Gueven, T. D. Ashton and F. M. Pfeffer, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC01251C

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