Merck
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172050

Sigma-Aldrich

Anacardic Acid - CAS 16611-84-0 - Calbiochem

The Anacardic Acid, also referenced under CAS 16611-84-0, modulates the biological activity of Anacardic. This small molecule/inhibitor is primarily used for Cell Structure applications.

Synonym(s):
Anacardic Acid - CAS 16611-84-0 - Calbiochem, AA, 2-Hydroxy-6-pentadecylbenzoic Acid, 6-Pentadecylsalicylic Acid, Aurora Kinase A Activator, Histone Acetyltransferase Inhibitor III, SUMOylation Inhibitor II, HAT Inhibitor III, p300/CBP Inhibitor III, PCAF Inhibitor I
Empirical Formula (Hill Notation):
C22H36O3
CAS Number:
Molecular Weight:
348.52
MDL number:

Quality Level

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 10 mg/mL
ethanol: 10 mg/mL
methanol: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C22H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h15,17-18,23H,2-14,16H2,1H3,(H,24,25)

InChI key

ADFWQBGTDJIESE-UHFFFAOYSA-N

General description

A cell-permeable ginkgolic acid (Cat. No. 345887) analog that inhibits protein SUMO (Cat. Nos. 662037, 662039, and 662042) modification (IC50 = 2.2 µM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. Nos. 662073 and 662074) and interfering with E1-SUMO intermediate formation. Both anacardic acid and ginkgolic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although anacardic acid is shown to inhibit p300 (Cat. No. 506200) and PCAF (Cat. No. 124026) histone acetyltransferase activities in cell-free acetylase assays (by 82% and 86%, respectively, at 10 µM). Also reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, as well as to enhance Aurora kinase A (Cat. No. 481413), but not Aurora kinase B, autophosphorylation and kinase activity by inducing conformation change and enhancing ATP binding.
A cell-permeable ginkgolic acid (Cat. No. 345887) analog that inhibits protein SUMO (Cat. Nos. 662037, 662039, and 662042) modification (IC50 = 2.2 µM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. Nos. 662073 and 662074) and interfering with E1-SUMO intermediate formation. Both anacardic acid and ginkgolic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although anacardic acid is shown to inhibit p300 (Cat. No. 506200) and PCAF (Cat. No. 124026) histone acetyltransferase activities in cell-free acetylase assays (by 82% and 86%, respectively, at 10 µM). Also reported to inhibit the activity of prostaglandin synthase, tyrosinase, and lipoxygenase, as well as to enhance Aurora kinase A (Cat. No. 481413), but not Aurora kinase B, autophosphorylation and kinase activity by inducing conformation change and enhancing ATP binding.

Packaging

10 mg in Plastic ampoule
Packaged under inert gas

Biochem/physiol Actions

Cell permeable: yes
Primary Target
HAT
Product competes with ATP.
Reversible: no
Target IC50: 5 µM against HAT; 8.5 µM against PCAF; 2.2 µM inhibiting protein SUMO modification using RanGAP1-C2 as substrate

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Fukuda, I., et al. 2009. Chem. Biol.16, 133.
Kishore, A.H. 2008. J. Med. Chem.51, 792.
Balasubramanyam, K., et al. 2003. J. Biol. Chem.278, 19134.
Paramashivappa, R., et al. 2002. J. Agric. Food Chem.50, 7709.

Legal Information

Sold under license of U.S. Patent 7,332,629 and related patents.
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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