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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: | 4 |
| Deposited By: | Pharmacy |
| Deposited On: | 2021-06-23 |
| Last Modified: | 2021-09-30 |
| Downloads: | 14 View Download Statistics |
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