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Merck
모든 사진(1)

Key Documents

172050

Sigma-Aldrich

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.

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C22H36O3
CAS Number:
Molecular Weight:
348.52
MDL number:
UNSPSC 코드:
12352106
NACRES:
NA.77

Quality Level

분석

≥95% (HPLC)

형태

solid

제조업체/상표

Calbiochem®

저장 조건

OK to freeze
protect from light

색상

white

solubility

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

배송 상태

ambient

저장 온도

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

일반 설명

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.

생화학적/생리학적 작용

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

포장

Packaged under inert gas

경고

Toxicity: Standard Handling (A)

재구성

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

기타 정보

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.

법적 정보

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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