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345887

Sigma-Aldrich

Ginkgolic Acid (15:1)

A cell-permeable anacardic acid analog that inhibits protein SUMO .

Synonym(s):

Ginkgolic Acid (15:1), (Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, SUMOylation Inhibitor, HAT Inhibitor VI, Histone Acetyltransferase Inhibitor VI, PCAF Inhibitor II, SUMOylation Inhibitor, (Z)-6-(Pentadec-8-enyl)-2-hydroxybenzoic acid, HAT Inhibitor VI

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About This Item

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

Quality Level

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 100 mg/mL
ethanol: 100 mg/mL

shipped in

ambient

storage temp.

−20°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. Nos. 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. Nos. 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. Also available as a 25 mM solution in DMSO (Cat. No. 508197).
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.

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Reconstitution

Following intitial thaw, aliquot and freeze (-20°C).

Other Notes

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

Legal Information

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

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Aquatic Chronic 4 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

509.9 °F - (calculated)

Flash Point(C)

265.5 °C - (calculated)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Wenjun Wang et al.
Journal of agricultural and food chemistry, 67(36), 10097-10106 (2019-08-17)
Ginkgolic acids (GAs) are found in the leaves, nuts, and testa of Ginkgo biloba and have been reported to exhibit antitumor, antibacterial, and pro-apoptotic activities. However, their role in mitochondrial function is still unclear. Our previous study showed that genes

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