172050

Kwas anakardowy

≥95% (HPLC), SUMO-activating enzyme E1 inhibitor, solid

• Synonim(y): AA, kwas 2-hydroksy-6-pentadecylobenzoesowy, kwas 6-pentadecylosalicylowy, aktywator kinazy Aurora, inhibitor acetylotransferazy histonowej III, inhibitor SUMOylacji II, inhibitor HAT III, inhibitor p300/CBP III, inhibitor PCAF I
• Wzór empiryczny (zapis Hilla): C₂₂H₃₆O₃
• Numer CAS: 16611-84-0
• Masa cząsteczkowa: 348.52
• UNSPSC Code: 12352106
• NACRES: NA.77
• MDL number: MFCD07368254
• Assay: ≥95% (HPLC)
• Form: solid
• Storage condition: OK to freeze, protect from light

Właściwości

• Nazwa produktu: Kwas anakardowy, 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.
• Quality Segment: 100
• 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
• SMILES string: Oc1c(c(ccc1)CCCCCCCCCCCCCCC)C(=O)O
• 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

Opis

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.

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

Packaging

Packaged under inert gas

Preparation Note

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

Disclaimer

Toxicity: Standard Handling (A)

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Informacja o środkach bezpieczeństwa

• Klasa składowania: 11 - Combustible Solids
• wgk: WGK 3