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Gambogic Acid (Guttatic Acid, Guttic Acid)

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InvivoChem Cat #: V0033

CAS #: 2752-65-0Purity ≥98%

Description: Gambogic Acid (also called Guttatic Acid, Guttic Acid) is a naturally occurring xanthonoid isolated from the brownish or orange resin from Garcinia hanburyi. It has potential antitumor activity and is currently undergoing clinical trials in China. The mechanism of action for Gambogic Acid is to activate caspases with EC50 of 0.78-1.64 μM and competitively inhibit Bcl-XL, 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. The cytotoxic natural product GA competes for BH3 peptide binding sites on several antiapoptotic members of the Bcl-2 family and neutralizes the ability of these proteins to suppress release of apoptogenic proteins from mitochondria. In vitro, it was demonstrated that GA inhibited the proliferation of human gastric carcinoma MGC-803 cells in a dose-dependent manner. When the cells were exposed to GA 5 mg/ml for 72 h, the rate of inhibition reached 89.45%.

References: Mol Cancer Ther. 2008 Jun;7(6):1639-46; Bioorg Med Chem. 2004 Jan 15;12(2):309-17.

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Molecular Weight (MW)	628.75
Formula	C38H44O8
CAS No.	2752-65-0
Storage	-20℃ for 3 years in powder form
Storage	-80℃ for 2 years in solvent
Solubility (In vitro)	DMSO: 100 mg/mL (159.04 mM)
	Water:<1 mg/mL (slightly soluble or insoluble)
	Ethanol: N/A
Synonyms	ß-Guttiferrin; ß-Guttiferrin; ß-Guttilactone; Cambogic acid; Guttatic acid; Guttic acid.
Other info	Chemical Name: (Z)-4-((1S,3aR,5S,11R,14aS)-8-hydroxy-2,2,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-4,7-dioxo-2,3a,4,5,7,11-hexahydro-1H-1,5-methanofuro[3,2-g]pyrano[3,2-b]xanthen-3a-yl)-2-methylbut-2-enoic acid InChi Key: GEZHEQNLKAOMCA-RRZNCOCZSA-N InChi Code: InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1 SMILES Code: O=C(O)/C(C)=C\C[C@@](C([C@]1([H])C=C23)=O)(OC(C)(C)[C@]4([H])C1)[C@@]24OC5=C(C(O)=C(C=C[C@](CC/C=C(C)/C)(C)O6)C6=C5C/C=C(C)\C)C3=O

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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. The results indicated that iv injection of GGA 2, 4, and 8 mg/kg inhibited dramatically the growth of human hepatocellular cell line SMMC-7721 in nude mice from the early administration.
Animal model	BALB/c nude mice bearing SMMC-7721 xenografts
Formulation & Dosage	Intravenous injection, 2, 4, and 8 mg/kg, 3 times per week
References	Acta Pharmacologica Sinica, 2004, 25: 769-774.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Lot#: V003301=Purity ≥98%
COV
MSDS
NMR

Lot#: V003302=Purity ≥98%
COA
MSDS
NMR

Gambogic acid neutralizes ability of Bcl-2-family proteins to suppress tBid-induced mitochondrial leakage. Zhai D, et al. Mol Cancer Ther. 2008 Jun;7(6):1639-46.	Gambogic acid inhibits binding of FITC-BH3 peptide to anti-apoptotic Bcl-2 family proteins. Mol Cancer Ther. 2008 Jun;7(6):1639-46.	Effects of Bcl-2 over-expression or Bax/Bak DKO on Gambogic acid-induced cytotoxicity. Mol Cancer Ther. 2008 Jun;7(6):1639-46.
TR-FRET assay confirms gambogic acid competes with BH3 peptide for binding to Bcl-XL. Mol Cancer Ther. 2008 Jun;7(6):1639-46.	Gambogic acid induces apoptosis of cancer cells. Mol Cancer Ther. 2008 Jun;7(6):1639-46.	Comparison of cytotoxic activity and BH3 peptide displacement activity of Gambogic acid and analogs. Mol Cancer Ther. 2008 Jun;7(6):1639-46.

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