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

Hearn, Kyle N, Ashton, Trent D, Acharya, Rameshwor, Feng, Zikai, Gueven, Nuri and Pfeffer, Frederick M 2021, Direct amidation to access 3-amido-1,8-naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors, Cells, vol. 10, no. 6, pp. 1-10, doi: 10.3390/cells10061505.

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Title Direct amidation to access 3-amido-1,8-naphthalimides including fluorescent scriptaid analogues as HDAC inhibitors
Author(s) Hearn, Kyle N
Ashton, Trent DORCID iD for Ashton, Trent D orcid.org/0000-0002-6707-6064
Acharya, Rameshwor
Feng, Zikai
Gueven, Nuri
Pfeffer, Frederick MORCID iD for Pfeffer, Frederick M orcid.org/0000-0002-5441-6437
Journal name Cells
Volume number 10
Issue number 6
Article ID 1505
Start page 1
End page 10
Total pages 10
Publisher MDPI
Place of publication Basel, Switzerland
Publication date 2021-06
ISSN 2073-4409
2073-4409
Keyword(s) Buchwald-Hartwig
Cell Biology
fluorescence
histone deacetylase
imaging
Life Sciences & Biomedicine
Science & Technology
scriptaid
tubulin deacetylase
1,8-naphthalimide
HDAC
HISTONE DEACETYLASE INHIBITOR
NAPHTHALIMIDE DERIVATIVES
ANTICANCER
POTENT
PROBES
AGENTS
Summary 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.
Language eng
DOI 10.3390/cells10061505
Indigenous content off
HERDC Research category C1 Refereed article in a scholarly journal
ERA Research output type C Journal article
Free to Read? Yes
Persistent URL http://hdl.handle.net/10536/DRO/DU:30152800

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Created: Thu, 24 Jun 2021, 14:51:32 EST

Every reasonable effort has been made to ensure that permission has been obtained for items included in DRO. If you believe that your rights have been infringed by this repository, please contact drosupport@deakin.edu.au.