1009815-87-5
Chemical Structure
Largazole
Synonym(s): (+)-Largazole
- CAS No.: 1009815-87-5
- Formula:C29H42N4O5S3
- Molecular Weight:622.86
IUPAC Name: S-((E)-4-((12Z,22Z,24R,5S,8S)-5-isopropyl-24-methyl-3,6,10-trioxo-24,25-dihydro-7-oxa-4,11-diaza-1(4,2),2(2,4)-dithiazolacyclododecaphane-8-yl)but-3-en-1-yl) octanethioate
InChIKey: AXESYCSCGBQJBL-SZPBEECKSA-N
SMILES: CCCCCCCC(SCC/C=C/[C@H](CC(NC1)=O)OC([C@H](C(C)C)NC([C@]2(C)CSC(C3=CSC1=N3)=N2)=O)=O)=O
Biological Activity: Largazole ((+)-Largazole) is an orally active, blood-brain barrier-permeable class I histone deacetylase (HDAC) inhibitor with in vivo anticancer activity and osteogenic efficacy. As a prodrug, Largazole hydrolyzes to Largazole thiol (HY-170890), which has a Ki value of 0.07 nM against human HDAC2. Largazole regulates the cell cycle, induces apoptosis, upregulates tumor suppressors and osteoblast differentiation markers, inhibits osteoclast formation, and upregulates neuroprotection-related genes. Largazole can be used in the research of various cancers including colorectal cancer, as well as neurodegenerative diseases[1][2][3][4].
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Largazole | Largazole ((+)-Largazole) is an orally active, blood-brain barrier-permeable class I histone deacetylase (HDAC) inhibitor with in vivo anticancer activity and osteogenic efficacy. As a prodrug, Largazole hydrolyzes to Largazole thiol (HY-170890), which has a Ki value of 0.07 nM against human HDAC2. Largazole regulates the cell cycle, induces apoptosis, upregulates tumor suppressors and osteoblast differentiation markers, inhibits osteoclast formation, and upregulates neuroprotection-related genes. Largazole can be used in the research of various cancers including colorectal cancer, as well as neurodegenerative diseases. | |||||||||||||||||||||
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- [1]. Hong J, et al. Largazole: from discovery to broad-spectrum therapy. Natural product reports. 2012 Apr;29(4):449-56. [Content Brief]
- [2]. Al-Awadhi FH, et al. Largazole is a Brain-Penetrant Class I HDAC Inhibitor with Extended Applicability to Glioblastoma and CNS Diseases. ACS chemical neuroscience. 2020 Jul 01;11(13):1937-1943. [Content Brief]
- [3]. Bowers A, et al. Total synthesis and biological mode of action of largazole: a potent class I histone deacetylase inhibitor. Journal of the American Chemical Society. 2008 Aug 20;130(33):11219-22. [Content Brief]
- [4]. Taori K, et al. Structure and Activity of Largazole, a Potent Antiproliferative Agent from the Floridian Marine Cyanobacterium Symploca sp. Journal of the American Chemical Society, 2008, 130(6): 1806-1807.
Keywords
