5.08197

Ginkgolic Acid (15:1)

InSolution, ≥98%, 25 mM in DMSO

• Synonym(s): InSolution Ginkgolic Acid (15:1), Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, HAT Inhibitor VI, SUMOylation Inhibitor, ( Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, ( Z)-2-Hydroxy-6-(pentadec-8-enyl)benzoic acid, Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, HAT Inhibitor VI, SUMOylation Inhibitor, (Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, (Z)-2-Hydroxy-6-(pentadec-8-enyl)benzoic acid
• Empirical Formula (Hill Notation): C₂₂H₃₄O₃
• CAS Number: 22910-60-7
• Molecular Weight: 346.50
• UNSPSC Code: 12352106
• NACRES: NA.77
• MDL number: MFCD03093717
• Assay: ≥98% (HPLC)
• Form: liquid
• Storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light

Properties

• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: liquid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, avoid repeated freeze/thaw cycles, desiccated (hygroscopic), protect from light
• storage temp.: −70°C
• SMILES string: Oc1c(c(ccc1)CCCCCCC\C=C/CCCCCC)C(=O)O
• InChI: 1S/C22H34O3/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/h7-8,15,17-18,23H,2-6,9-14,16H2,1H3,(H,24,25)/b8-7-
• InChI key: YXHVCZZLWZYHSA-FPLPWBNLSA-N

Description

General description

A cell-permeable anacardic acid (Cat. No. 172050) analog that inhibits protein SUMO (Cat. No. 662037, 662039, and 662042) modification (IC₅₀ = 3.0 µM using RanGAP1-C2 as substrate) in an ATP-dependent manner by selectively targeting SUMO-activating enzyme E1 (Cat. No. 662073 and 662074) and interfering with E1-SUMO intermediate formation independent of E1 active site cysteine. Both ginkgolic acid and anacardic acid are shown to effectively decrease overall SUMOylation of 293T cellular proteins, including p53, in a dose-dependent manner, while neither compound is effective in affecting overall cellular protein ubiquitination or histone H4K8 acetylation in 293T cultures, although both compounds are shown to inhibit histone lysine acetylation by PCAF (Cat. No. 124026) in cell-free acetylase assays.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
SUMO-activating enzyme E1

Reversible: yes

Packaging

Packaged under inert gas

Physical form

A 25 mM (2 mg/231 µl) sterile-filtered solution of Ginkgolic Acid (15:1) (Cat. No. 345887) in DMSO.

Preparation Note

Following initial thaw, aliquot and freeze (-20°C). Aliquots are stable for up to 6 months at -20°C. Use only fresh DMSO for further dilutions.

Other Notes

Fukuda, I., et al. 2009. Chem. Biol.16, 133.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk: WGK 2
• flash_point_f: 188.6 °F - (refers to pure substance)
• flash_point_c: 87 °C - (refers to pure substance)