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2752-65-0,MFCD16878985
Catalog No.:AA00BD75

2752-65-0 | Gambogic acid

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1mg
≥95% (mixture of epimers)
in stock  
$48.00   $33.00
- +
5mg
95%
in stock  
$81.00   $57.00
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10mg
95%
in stock  
$159.00   $112.00
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25mg
≥95% (mixture of epimers)
in stock  
$272.00   $190.00
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100mg
95%
in stock  
$303.00   $212.00
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250mg
95%
in stock  
$427.00   $299.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BD75
Chemical Name:
Gambogic acid
CAS Number:
2752-65-0
Molecular Formula:
C38H44O8
Molecular Weight:
628.7512
MDL Number:
MFCD16878985
SMILES:
CC(=CCc1c2O[C@]34[C@@]5(C/C=C(\C(=O)O)/C)OC([C@@H]4C[C@H](C5=O)C=C3C(=O)c2c(c2c1O[C@](C)(CCC=C(C)C)C=C2)O)(C)C)C
Properties
Computed Properties
 
Complexity:
1490  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
46  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
8  
XLogP3:
7.3  

Downstream Synthesis Route
21043-40-3    2752-65-0   
1-gambogyl-4-cyclopentylpiperazine 

[1]BioorganicandMedicinalChemistry,2004,vol.12,p.309-317

67-56-1    2752-65-0   
gambogoicacid 

[1]BiologicalandPharmaceuticalBulletin,2005,vol.28,p.2335-2337

2752-65-0   
methyl6-O-methylgambogate 

[1]BioorganicandMedicinalChemistry,2004,vol.12,p.309-317

[1]EuropeanJournalofMedicinalChemistry,2009,vol.44,p.2611-2620

[1]EuropeanJournalofMedicinalChemistry,2009,vol.44,p.2611-2620

Literature

Title: Gambogic acid sensitizes resistant breast cancer cells to doxorubicin through inhibiting P-glycoprotein and suppressing survivin expression.

Journal: Chemico-biological interactions 20150625

Title: Calcium channel blocker verapamil accelerates gambogic acid-induced cytotoxicity via enhancing proteasome inhibition and ROS generation.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20140401

Title: The combination of proteasome inhibitors bortezomib and gambogic acid triggers synergistic cytotoxicity in vitro but not in vivo.

Journal: Toxicology letters 20140130

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Gambogic acid is a novel anti-cancer agent that inhibits cell proliferation, angiogenesis and metastasis.

Journal: Anti-cancer agents in medicinal chemistry 20121001

Title: Gambogic acid deactivates cytosolic and mitochondrial thioredoxins by covalent binding to the functional domain.

Journal: Journal of natural products 20120622

Title: Design and synthesis of gambogic acid analogs as potent cytotoxic and anti-inflammatory agents.

Journal: Bioorganic & medicinal chemistry letters 20120615

Title: Enhancement of anticancer efficacy of chemotherapeutics by gambogic acid against gastric cancer cells.

Journal: Cancer biotherapy & radiopharmaceuticals 20120601

Title: [Reversal effect of gambogic acid on multidrug resistance of K562/A02 cell line].

Journal: Zhongguo shi yan xue ye xue za zhi 20120401

Title: Synthesis and biological evaluation of novel derivatives of gambogic acid as anti-hepatocellular carcinoma agents.

Journal: Bioorganic & medicinal chemistry letters 20120101

Title: Prenylated caged xanthones: chemistry and biology.

Journal: Pharmaceutical biology 20120101

Title: Poloxamer 407/TPGS mixed micelles for delivery of gambogic acid to breast and multidrug-resistant cancer.

Journal: International journal of nanomedicine 20120101

Title: Gambogic acid-loaded magnetic Fe(3)O(4) nanoparticles inhibit Panc-1 pancreatic cancer cell proliferation and migration by inactivating transcription factor ETS1.

Journal: International journal of nanomedicine 20120101

Title: Synergistic anti-proliferative effects of gambogic acid with docetaxel in gastrointestinal cancer cell lines.

Journal: BMC complementary and alternative medicine 20120101

Title: Induction of programmed erythrocyte death by gambogic acid.

Journal: Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20120101

Title: Gambogic acid inhibits tumor cell adhesion by suppressing integrin β1 and membrane lipid rafts-associated integrin signaling pathway.

Journal: Biochemical pharmacology 20111215

Title: Src regulates Tyr(20) phosphorylation of transferrin receptor-1 and potentiates breast cancer cell survival.

Journal: The Journal of biological chemistry 20111014

Title: [Role of chloride channels in gambogic acid-induced apoptosis of poorly differentiated nasopharyngeal carcinoma cells].

Journal: Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20110801

Title: Gambogic acid inhibits STAT3 phosphorylation through activation of protein tyrosine phosphatase SHP-1: potential role in proliferation and apoptosis.

Journal: Cancer prevention research (Philadelphia, Pa.) 20110701

Title: Gambogic acid, a natural product inhibitor of Hsp90.

Journal: Journal of natural products 20110527

Title: Absolute configuration of (-)-gambogic acid, an antitumor agent.

Journal: Journal of natural products 20110325

Title: Gambogic acid enhances proteasome inhibitor-induced anticancer activity.

Journal: Cancer letters 20110227

Title: Gambogic acid-induced degradation of mutant p53 is mediated by proteasome and related to CHIP.

Journal: Journal of cellular biochemistry 20110201

Title: Study of the enhanced anticancer efficacy of gambogic acid on Capan-1 pancreatic cancer cells when mediated via magnetic Fe3O4 nanoparticles.

Journal: International journal of nanomedicine 20110101

Title: In vitro screening for angiostatic potential of herbal chemicals.

Journal: Investigative ophthalmology & visual science 20101201

Title: Gambogic acid triggers DNA damage signaling that induces p53/p21(Waf1/CIP1) activation through the ATR-Chk1 pathway.

Journal: Cancer letters 20101001

Title: Gambogic acid induces G0/G1 cell cycle arrest and cell migration inhibition via suppressing PDGF receptor β tyrosine phosphorylation and Rac1 activity in rat aortic smooth muscle cells.

Journal: Journal of atherosclerosis and thrombosis 20100930

Title: Apoptotic activity of caged xanthones from Garcinia hanburyi in cholangiocarcinoma cell lines.

Journal: World journal of gastroenterology 20100514

Title: Identification and quantitative determination of a major circulating metabolite of gambogic acid in human.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100301

Title: Comparison of electron capture-atmospheric pressure chemical ionization and electrospray ionization for the analysis of gambogic acid and its main circulating metabolite in dog plasma.

Journal: European journal of mass spectrometry (Chichester, England) 20100101

Title: [Apoptosis-inducing effect of gambogic acid on K562 cells and its mechanism].

Journal: Zhongguo shi yan xue ye xue za zhi 20091201

Title: Effect of Gambogic acid on the regulation of hERG channel in K562 cells in vitro.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20091001

Title: Gambogic acid induces G0/G1 arrest and apoptosis involving inhibition of SRC-3 and inactivation of Akt pathway in K562 leukemia cells.

Journal: Toxicology 20090803

Title: Reactive oxygen species accumulation contributes to gambogic acid-induced apoptosis in human hepatoma SMMC-7721 cells.

Journal: Toxicology 20090616

Title: GA3, a new gambogic acid derivative, exhibits potent antitumor activities in vitro via apoptosis-involved mechanisms.

Journal: Acta pharmacologica Sinica 20090301

Title: Synergistic effect of 5-fluorouracil with gambogic acid on BGC-823 human gastric carcinoma.

Journal: Toxicology 20090204

Title: Bioassay guided discovery of apoptosis inducers from gamboge by high-speed counter-current chromatography and high-pressure liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090201

Title: Gambogic acid induces apoptosis by regulating the expression of Bax and Bcl-2 and enhancing caspase-3 activity in human malignant melanoma A375 cells.

Journal: International journal of dermatology 20090201

Title: Proteomic identification of molecular targets of gambogic acid: role of stathmin in hepatocellular carcinoma.

Journal: Proteomics 20090101

Title: The NF-kappa B inhibitor, celastrol, could enhance the anti-cancer effect of gambogic acid on oral squamous cell carcinoma.

Journal: BMC cancer 20090101

Title: Synergistic effect of magnetic nanoparticles of Fe(3)O(4) with gambogic acid on apoptosis of K562 leukemia cells.

Journal: International journal of nanomedicine 20090101

Title: Gambogic acid mediates apoptosis as a p53 inducer through down-regulation of mdm2 in wild-type p53-expressing cancer cells.

Journal: Molecular cancer therapeutics 20081001

Title: Water-soluble gambogic acid PEGylated prodrugs: synthesis, characterization, physicochemical properties and in vitro hydrolysis.

Journal: Die Pharmazie 20081001

Title: [Analysis of xanthones in gamboge by HPLC-PDA-ESI/MS].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20080801

Title: Inhibition of alpha(4) integrin mediated adhesion was involved in the reduction of B16-F10 melanoma cells lung colonization in C57BL/6 mice treated with gambogic acid.

Journal: European journal of pharmacology 20080728

Title: [Effects of gambogic acid on the regulation of nucleoporin Nup88 in HL-60 cells].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology] 20080701

Title: Gambogic acid is an antagonist of antiapoptotic Bcl-2 family proteins.

Journal: Molecular cancer therapeutics 20080601

Title: Posttranscriptional regulation of the telomerase hTERT by gambogic acid in human gastric carcinoma 823 cells.

Journal: Cancer letters 20080418

Title: Gambogic acid, a potent inhibitor of survivin, reverses docetaxel resistance in gastric cancer cells.

Journal: Cancer letters 20080418

Title: Synthesis of caged 2,3,3a,7a-tetrahydro-3,6-methanobenzofuran-7(6H)-ones: Evaluating the minimum structure for apoptosis induction by gambogic acid.

Journal: Bioorganic & medicinal chemistry 20080415

Title: Gambogic acid induces death inducer-obliterator 1-mediated apoptosis in Jurkat T cells.

Journal: Acta pharmacologica Sinica 20080301

Title: Preparation, physical properties, and stability of gambogic acid-loaded micelles based on chitosan derivatives.

Journal: Drug development and industrial pharmacy 20080101

Title: Gambogic acid inhibits angiogenesis through suppressing vascular endothelial growth factor-induced tyrosine phosphorylation of KDR/Flk-1.

Journal: Cancer letters 20071208

Title: Gambogic acid, a novel ligand for transferrin receptor, potentiates TNF-induced apoptosis through modulation of the nuclear factor-kappaB signaling pathway.

Journal: Blood 20071115

Title: Gambogic acid inhibits the catalytic activity of human topoisomerase IIalpha by binding to its ATPase domain.

Journal: Molecular cancer therapeutics 20070901

Title: Effects of gambogic acid on the regulation of nucleoporin Nup88 in U937 cells.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20070801

Title: Gambogic acid-induced G2/M phase cell-cycle arrest via disturbing CDK7-mediated phosphorylation of CDC2/p34 in human gastric carcinoma BGC-823 cells.

Journal: Carcinogenesis 20070301

Title: Determination of gambogic acid in dog plasma by high-performance liquid chromatography for a pharmacokinetic study.

Journal: Biomedical chromatography : BMC 20070301

Title: Determination of gambogic acid in human plasma by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070201

Title: Preparative separation of gambogic acid and its C-2 epimer using recycling high-speed counter-current chromatography.

Journal: Journal of chromatography. A 20060915

Title: Metabolism and metabolic inhibition of gambogic acid in rat liver microsomes.

Journal: Acta pharmacologica Sinica 20060901

Title: Stability and cytotoxicity of gambogic acid and its derivative, gambogoic acid.

Journal: Biological & pharmaceutical bulletin 20051201

Title: Anticancer effect and apoptosis induction of gambogic acid in human gastric cancer line BGC-823.

Journal: World journal of gastroenterology 20050628

Title: Gambogic acid inhibits proliferation of human lung carcinoma SPC-A1 cells in vivo and in vitro and represses telomerase activity and telomerase reverse transcriptase mRNA expression in the cells.

Journal: Biological & pharmaceutical bulletin 20041101

Title: Zhai D, et al. Gambogic acid is an antagonist of antiapoptotic Bcl-2 family proteins. Mol Cancer Ther. 2008 Jun;7(6):1639-46.

Title: Wang LH, et al. Gambogic acid synergistically potentiates cisplatin-induced apoptosis in non-small-cell lung cancer through suppressing NF-κB and MAPK/HO-1 signalling. Br J Cancer. 2014 Jan 21;110(2):341-52.

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