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AB144480

SAHA (Vorinostat), HDAC inhibitor

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(1 Publication)

MW 264.32 Da, Purity >98%. Potent non-selective HDAC inhibitor (IC50 values are 10 and 20 nM for HDAC1 and HDAC3, respectively). Induces apoptosis and shows antiproliferative effects against cancer cell lines (IC50 = 3 - 8 μM). Antitumor effects in vivo. No effect on class III HDACs. Orally active.

View Alternative Names

AHO3, Antigen NY-CO-9, BDMR, CDA07, CDLS5, CPBHM, D10Wsu179e, DKFZP586J0917, DKFZP761B039, DKFZp686H12203, EC 3.5.1.98, FLJ16239, FLJ22237, FLJ99588, GON 10, HA6116, HD 10, HD 11, HD 2, HD 4, HD 6, HD 7, HD 7B, HD 7a, HD 8, HD 9, HD1, HD3, HD5, HDA10_HUMAN, HDA11_HUMAN, HDAC, HDAC 11, HDAC 7A, HDAC 7B, HDAC 9B, HDAC 9FL, HDAC A, HDAC1_HUMAN, HDAC2_HUMAN, HDAC3_HUMAN, HDAC4_HUMAN, HDAC5_HUMAN, HDAC6_HUMAN, HDAC7_HUMAN, HDAC8_HUMAN, HDAC9_HUMAN, HDACL-1, HDRP, Histone Deacetylase A, Histone deacetylase 1, Histone deacetylase 10, Histone deacetylase 11, Histone deacetylase 2, Histone deacetylase 2 (HD2), Histone deacetylase 3, Histone deacetylase 4, Histone deacetylase 4/5 related protein, Histone deacetylase 5, Histone deacetylase 6, Histone deacetylase 6 (HD6), Histone deacetylase 7, Histone deacetylase 7A, Histone deacetylase 7B, Histone deacetylase 8, Histone deacetylase 9, Histone deacetylase 9A, Histone deacetylase like 1, Histone deacetylase-related protein, JM 21, KIAA0288, KIAA0744, KIAA0901, MEF2 interacting transcription repressor protein, MEF2-interacting transcription repressor MITR, MGC149722, MITR, MRXS6, NY CO 9, OTTHUMP00000017046, OTTHUMP00000028555, OTTHUMP00000032398, OTTHUMP00000197663, OTTHUMP00000202813, OTTHUMP00000202814, OTTHUMP00000227077, OTTHUMP00000227078, PPP1R90, Protein phosphatase 1 regulatory subunit 90, RPD 3, RPD3-2, RPD3L1, Reduced potassium dependency yeast homolog like 1, SMAP45, WTS, YAF1, YY1 associated factor 1, YY1 transcription factor binding protein, Yy1bp, transcriptional regulator homolog RPD3

Key facts

CAS number

149647-78-9

Purity

>98%

Form

Solid

form

Molecular weight

264.32 Da

Molecular formula

C<sub>1</sub><sub>4</sub>H<sub>2</sub><sub>0</sub>N<sub>2</sub>O<sub>3</sub>

PubChem

5311

Nature

Synthetic

Solubility

Soluble in ethanol to 50 mM (with warming)

Soluble in DMSO to 100mM

Biochemical name

Vorinostat

Biological description

Potent non-selective HDAC inhibitor (IC50 values are 10 and 20 nM for HDAC1 and HDAC3, respectively). Induces apoptosis and shows antiproliferative effects against cancer cell lines (IC50 = 3 - 8 μM). Antitumor effects in vivo. No effect on class III HDACs. Orally active.

Canonical smiles

C1=CC=C(C=C1)NC(=O)CCCCCCC(=O)NO

InChi

InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)

InChiKey

WAEXFXRVDQXREF-UHFFFAOYSA-N

IUPAC Name

N'-hydroxy-N-phenyloctanediamide

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
Store under desiccating conditions|The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Histone deacetylases collectively known as HDACs include the enzymes HDAC1 HDAC2 HDAC3 HDAC4 HDAC5 HDAC6 HDAC7 HDAC8 HDAC9 HDAC10 and HDAC11. These proteins remove acetyl groups from histone proteins influencing chromatin structure and gene expression. HDAC1 for example has a molecular mass of approximately 55 kDa and is highly expressed in the nucleus of cells where it modifies chromatin architecture. The activity of these enzymes is tightly regulated and they often act as part of multi-subunit complexes to ensure precise control over transcription.
Biological function summary

HDACs play important roles in the regulation of gene expression by modifying the acetylation status of histones. They are integral parts of larger protein complexes such as the Sin3 complex or the NuRD complex which mediate interactions with chromatin to repress transcription. Through these complexes HDACs contribute to cell cycle regulation differentiation and apoptosis. The balance between acetylation and deacetylation maintained by HDACs and histone acetyltransferases (HATs) is critical for normal cellular function.

Pathways

These enzymes are essential in signaling and regulatory networks such as the Notch and p53 pathways. HDAC1 for instance interacts with the p53 protein to regulate cell cycle arrest and apoptosis. In the Notch signaling pathway HDACs participate in the regulation of cell fate determination. Their activity in these pathways often involves collaboration with other proteins including co-repressor proteins to exert their biological effects.

The dysregulation of HDAC activity has been associated with cancer and neurodegenerative diseases. In cancers such as leukemia aberrant HDAC1 activity can lead to uncontrolled cell proliferation due to the repression of tumor suppressor genes. In neurodegenerative conditions like Alzheimer's disease irregular HDAC6 function affects neuronal cell death and cognitive deficits. The therapeutic targeting of HDACs with inhibitors like SAHA (vorinostat) has shown promise in modulating these diseases highlighting the importance of HDACs as drug targets.

Product protocols

Publications (1)

Recent publications for all applications. Explore the full list and refine your search

Cell metabolism 30:903-916.e7 PubMed31523006

2019

Nuclear Glycogenolysis Modulates Histone Acetylation in Human Non-Small Cell Lung Cancers.

Applications

Unspecified application

Species

Unspecified reactive species

Ramon C Sun,Vikas V Dukhande,Zhengqiu Zhou,Lyndsay E A Young,Shane Emanuelle,Christine Fillmore Brainson,Matthew S Gentry
View all publications

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