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Direct amidation to access 3-Amido-1,8-naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors

Citation

Hearn, KN and Ashton, TD and Acharya, R and Feng, Z and Gueven, N and Pfeffer, FM, Direct amidation to access 3-Amido-1,8-naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors, Cells, 10 pp. 1-10. ISSN 2073-4409 (2021) [Refereed Article]


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Copyright Statement

Copyright: © 2021 by the author. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution 4.0 International (CC BY 4.0) license (https://creativecommons.org/licenses/by/4.0/).

DOI: doi:10.3390/cells10061505

Abstract

Methodology to access fluorescent 3-amido-1,8-naphthalimides using direct Buchwald– Hartwig amidation is described. The protocol was successfully used to couple a number of substrates (including an alkylamide, an arylamide, a lactam and a carbamate) to 3-bromo-1,8-naphthalimide in good yield. To further exemplify the approach, a set of scriptaid analogues with amide substituents at the 3-position were prepared. The new compounds were more potent than scriptaid at a number of histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in a whole cell tubulin deacetylation assay where the inhibitors were more active than the established HDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compounds make them amenable to cellular imaging studies and theranostic applications.

Item Details

Item Type:Refereed Article
Keywords:Buchwald–Hartwig, scriptaid, histone deacetylase, HDAC, 1,8-naphthalimide, fluorescence, imaging, tubulin deacetylase
Research Division:Biomedical and Clinical Sciences
Research Group:Pharmacology and pharmaceutical sciences
Research Field:Pharmaceutical sciences
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the biomedical and clinical sciences
UTAS Author:Acharya, R (Mr Rameshwor Acharya)
UTAS Author:Feng, Z (Mr Zikai Feng)
UTAS Author:Gueven, N (Dr Nuri Guven)
ID Code:144973
Year Published:2021
Web of Science® Times Cited:1
Deposited By:Pharmacy
Deposited On:2021-06-23
Last Modified:2021-09-30
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