172050

Anacardic Acid

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.

• 別名: Anacardic Acid, 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
• 実験式（ヒル表記法）: C₂₂H₃₆O₃
• CAS番号: 16611-84-0
• 分子量: 348.52
• MDL番号: MFCD07368254
• UNSPSCコード: 12352106
• NACRES: NA.77

特性

• 品質水準: 100
• アッセイ: ≥95% (HPLC)
• 形状: solid
• メーカー／製品名: Calbiochem^®
• 保管条件: OK to freeze; protect from light
• 色: white
• 溶解性: DMSO: 10 mg/mL; ethanol: 10 mg/mL; methanol: 10 mg/mL
• 輸送温度: ambient
• 保管温度: 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

詳細

詳細

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.

生物化学的／生理学的作用

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

包装

Packaged under inert gas

警告

Toxicity: Standard Handling (A)

再構成

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

その他情報

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.

法的情報

Sold under license of U.S. Patent 7,332,629 and related patents.

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

安全性情報

• 保管分類コード: 11 - Combustible Solids
• WGK: WGK 3