[CAS NO. 2752-65-0] Gambogic Acid

Name: Gambogic Acid
Brand: Arctom Scientific
SKU: SLK-S2448

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PRODUCTS SPECIFICATIONS [2752-65-0]

Distributor

Catalog

SLK-S2448

Brand

Selleck

CAS

2752-65-0

DESCRIPTION [2752-65-0]

Overview

MDL	MFCD16878985
Molecular Weight	628.75
Molecular Formula	C38H44O8
SMILES	C(/C=C(\C(O)=O)/C)[C@@]12[C@]34C(C(=O)C=5C(O3)=C(CC=C(C)C)C6=C(C5O)C=C[C@](CCC=C(C)C)(C)O6)=C[C@@H](C1=O)C[C@H]4C(C)(C)O2

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	1.5905 mL	7.9523 mL	15.9046 mL
5 mM	0.3181 mL	1.5905 mL	3.1809 mL
10 mM	0.1590 mL	0.7952 mL	1.5905 mL
50 mM	0.0318 mL	0.1590 mL	0.3181 mL

Description

Gambogic Acid (Guttatic Acid, Guttic Acid, Beta-Guttiferrin) activates caspases with EC50 of 0.78-1.64 μM and competitively inhibits Bcl-X, Bcl-2, Bcl-W, Bcl-B, Bfl-1 and Mcl-1 with IC50 of 1.47, 1.21, 2.02, 0.66, 1.06 and 0.79 μM, respectively.

Targets

In vitro

Gambogic Acid is a caged xanthone that is derived from Garcinia hanburyi and functions as a strong apoptotic inducer in many types of cancer cells by inhibiting human Bcl-2 family proteins and activating caspases. Gambogic Acid also blocks Kir2.1 channels with EC50 of ≤ 100 nM. Gambogic Acid significantly inhibits human umbilical vein endothelial cell (HUVEC) proliferation, migration, invasion, tube formation, and micro-vessel growth at nM concentration.

In vivo

Gambogic Acid effectively inhibits tumor angiogenesis and suppressed tumor growth with low side effects using metronomic chemotherapy with Gambogic Acid. Gambogic Acid has multiple functional effects including the induction of apoptosis, the inhibition of proliferation and the prevention of cancer metastasis and tumor angiogenesis. In both animal tumor models and clinical trials, Gambogic Acid efficiently inhibits tumor growth with minimal side effects, with little toxicity on immune and hemopoietic systems. Gambogic Acid can produce tissue-specific proteasome inhibition and tumor-specific toxicity. LD50: Mice 45mg/kg (i.p.).

References

[1] Zhai D, et al. Mol Cancer Ther, 2008, 7(6), 1639-1646.
[2] Zhang HZ, et al. Bioorg Med Chem, 2004, 12(2), 309-317.
[3] Pandey MK, et al. Blood, 2007, 110(10), 3517-3525.
[4] Yi T, et al. Cancer Res, 2008, 68(6), 1843–1850.
[5] Wang X, et al. Anticancer Agents Med Chem, 2012, 12(8), 994-1000.
[6] Li X, et al. Cell Rep, 2012, S2211-1247(12), 00420-00422.
[7] Guo Q, et al. Basic Clin Pharmacol Toxicol, 2006, 99(2), 178-184.

Synonyms

2-Butenoic acid, 2-methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-buten-1-yl)-11-(4-methyl-3-penten-1-yl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-, (2Z)-

1,5-Methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthene-1-crotonic acid, 3a,4,5,7-tetrahydro-8-hydroxy-α,3,3,11-tetramethyl-13-(3-methyl-2-butenyl)-11-(4-methyl-3-pentenyl)-7,15-dioxo-, (Z)-

Gambogic acid

2-Butenoic acid, 2-methyl-4-[3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-butenyl)-11-(4-methyl-3-pentenyl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-, [1R-[1α,1(Z),3aβ,5α,11β,14aS*]]-

2-Butenoic acid, 2-methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-butenyl)-11-(4-methyl-3-pentenyl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-, (2Z)-

(2Z)-2-Methyl-4-[(1R,3aS,5S,11R,14aS)-3a,4,5,7-tetrahydro-8-hydroxy-3,3,11-trimethyl-13-(3-methyl-2-buten-1-yl)-11-(4-methyl-3-penten-1-yl)-7,15-dioxo-1,5-methano-1H,3H,11H-furo[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-butenoic acid

β-Guttiferin

R-Gambogic acid

(-)-Gambogic acid

UI1907