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5.08197

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C22H34O3
CAS Number:
22910-60-7
Molecular Weight:
346.50
MDL number:
MFCD03093717
UNSPSC Code:
12352106
NACRES:
NA.77

Quality Level

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

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

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

Warning

Toxicity: Standard Handling (A)

Physical form

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

Reconstitution

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

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

188.6 °F - (refers to pure substance)

flash_point_c

87 °C - (refers to pure substance)

Certificates of Analysis (COA)

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Isao Fukuda et al.
Chemistry & biology, 16(2), 133-140 (2009-02-28)
Protein modification by small ubiquitin-related modifier proteins (SUMOs) controls diverse cellular functions. Dysregulation of SUMOylation or deSUMOylation processes has been implicated in the development of cancer and neurodegenerative diseases. However, no small-molecule inhibiting protein SUMOylation has been reported so far.

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