Martinostat

Martinostat
Identifiers
	IUPAC name (2E)-3-(4-{[(Adamantan-1-ylmethyl)(methyl)amino]methyl}phenyl)-N-hydroxyacrylamide;
CAS Number	1629052-58-9;
ChemSpider	34987952;
Chemical and physical data
Formula	C22H30N2O2
Molar mass	354.494 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(Cc1ccc(cc1)/C=C/C(=O)NO)CC23CC4CC(C2)CC(C4)C3;

Martinostat is a histone deacetylase inhibitor (HDACi) that is potent against recombinant class I HDACs (isoforms 1-3) and class IIb HDAC (isoform 6) with low nanomolar affinities.[1] In tissue CETSA assays,[2] martinostat exhibits selectivity for class I HDACs (isoforms 1-3).[3] When tagged with the radioisotope carbon-11, martinostat can be used to quantify HDAC in the brain and peripheral organs using positron emission tomography. Martinostat was given a name that adopted the style of other HDAC inhibitors, such as vorinostat, entinostat, and crebinostat, that recognized the academic center in which it was developed, the Martinos Center for Biomedical Imaging.

¹¹C-labeled martinostat

References

Wang, Changning; Schroeder, Frederick A.; Wey, Hsiao-Ying; Borra, Ronald; Wagner, Florence F.; Reis, Surya; Kim, Sung Won; Holson, Edward B.; Haggarty, Stephen J. (2014-09-18). "In Vivo Imaging of Histone Deacetylases (HDACs) in the Central Nervous System and Major Peripheral Organs". Journal of Medicinal Chemistry. 57 (19): 7999–8009. doi:10.1021/jm500872p. PMC 4191584. PMID 25203558.
Jafari, Rozbeh; Almqvist, Helena; Axelsson, Hanna; Ignatushchenko, Marina; Lundbäck, Thomas; Nordlund, Pär; Molina, Daniel Martinez (2014). "The cellular thermal shift assay for evaluating drug target interactions in cells". Nature Protocols. 9 (9): 2100–22. doi:10.1038/nprot.2014.138. PMID 25101824.
Wey, Hsiao-Ying; Gilbert, Tonya M.; Zürcher, Nicole R.; She, Angela; Bhanot, Anisha; Taillon, Brendan D.; Schroeder, Fredrick A.; Wang, Changing; Haggarty, Stephen J.; Hooker, Jacob M. (2016-08-10). "Insights into neuroepigenetics through human histone deacetylase PET imaging". Science Translational Medicine. 8 (351): 351ra106. doi:10.1126/scitranslmed.aaf7551. ISSN 1946-6234. PMC 5784409. PMID 27510902.

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[1] Wang, Changning; Schroeder, Frederick A.; Wey, Hsiao-Ying; Borra, Ronald; Wagner, Florence F.; Reis, Surya; Kim, Sung Won; Holson, Edward B.; Haggarty, Stephen J. (2014-09-18). "In Vivo Imaging of Histone Deacetylases (HDACs) in the Central Nervous System and Major Peripheral Organs". Journal of Medicinal Chemistry. 57 (19): 7999–8009. doi:10.1021/jm500872p. PMC 4191584. PMID 25203558.

[2] Jafari, Rozbeh; Almqvist, Helena; Axelsson, Hanna; Ignatushchenko, Marina; Lundbäck, Thomas; Nordlund, Pär; Molina, Daniel Martinez (2014). "The cellular thermal shift assay for evaluating drug target interactions in cells". Nature Protocols. 9 (9): 2100–22. doi:10.1038/nprot.2014.138. PMID 25101824.

[3] Wey, Hsiao-Ying; Gilbert, Tonya M.; Zürcher, Nicole R.; She, Angela; Bhanot, Anisha; Taillon, Brendan D.; Schroeder, Fredrick A.; Wang, Changing; Haggarty, Stephen J.; Hooker, Jacob M. (2016-08-10). "Insights into neuroepigenetics through human histone deacetylase PET imaging". Science Translational Medicine. 8 (351): 351ra106. doi:10.1126/scitranslmed.aaf7551. ISSN 1946-6234. PMC 5784409. PMID 27510902.