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MedKoo Cat#: 562229 | Name: Gambogenic Acid

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Gambogenic Acid is an inhibitor of the fibroblast growth factor receptor (FGFR) signaling pathway in erlotinib-resistant non-small-cell lung cancer (NSCLC). It acts by suppressing patient-derived xenograft growth.

Chemical Structure

Gambogenic Acid
Gambogenic Acid
CAS#173932-75-7

Theoretical Analysis

MedKoo Cat#: 562229

Name: Gambogenic Acid

CAS#: 173932-75-7

Chemical Formula: C38H46O8

Exact Mass: 630.3193

Molecular Weight: 630.77

Elemental Analysis: C, 72.36; H, 7.35; O, 20.29

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Gambogenic Acid; GNA;
IUPAC/Chemical Name
(Z)-4-((1S,3aR,5S,12aS)-9-((E)-3,7-dimethylocta-2,6-dien-1-yl)-8,10-dihydroxy-2,2-dimethyl-11-(3-methylbut-2-en-1-yl)-4,7-dioxo-1,2,5,7-tetrahydro-1,5-methanofuro[2,3-d]xanthen-3a(4H)-yl)-2-methylbut-2-enoic acid
InChi Key
RCWNBHCZYXWDOV-VSFMGBBVSA-N
InChi Code
InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/b22-13+,23-16-/t24-,28+,37+,38-/m1/s1
SMILES Code
O=C(O)/C(C)=C\C[C@]([C@@]12OC3=C4C(O)=C(C/C=C(C)/CC/C=C(C)\C)C(O)=C3C/C=C(C)\C)(OC(C)(C)[C@]2([H])C5)C([C@]5([H])C=C1C4=O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 630.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Xu L, Meng X, Xu N, Fu W, Tan H, Zhang L, Zhou Q, Qian J, Tu S, Li X, Lao Y, Xu H. Gambogenic acid inhibits fibroblast growth factor receptor signaling pathway in erlotinib-resistant non-small-cell lung cancer and suppresses patient-derived xenograft growth. Cell Death Dis. 2018 Feb 15;9(3):262. doi: 10.1038/s41419-018-0314-6. PubMed PMID: 29449529; PubMed Central PMCID: PMC5833807. 2: Liu P, Wu X, Dai L, Ge Z, Gao C, Zhang H, Wang F, Zhang X, Chen B. Gambogenic Acid Exerts Antitumor Activity in Hypoxic Multiple Myeloma Cells by Regulation of miR-21. J Cancer. 2017 Sep 16;8(16):3278-3286. doi: 10.7150/jca.19290. eCollection 2017. PubMed PMID: 29158801; PubMed Central PMCID: PMC5665045. 3: Li F, Wang Y, Yan Y. Gambogenic acid induces cell growth inhibition, cell cycle arrest and metastasis inhibition in choroidal melanoma in a dose-dependent manner. Exp Ther Med. 2017 May;13(5):2456-2462. doi: 10.3892/etm.2017.4252. Epub 2017 Mar 22. PubMed PMID: 28565863; PubMed Central PMCID: PMC5443308. 4: Chen R, Zhang H, Liu P, Wu X, Chen B. Gambogenic acid synergistically potentiates bortezomib-induced apoptosis in multiple myeloma. J Cancer. 2017 Mar 7;8(5):839-851. doi: 10.7150/jca.17657. eCollection 2017. PubMed PMID: 28382147; PubMed Central PMCID: PMC5381173. 5: Wang X, Cao W, Zhang J, Yan M, Xu Q, Wu X, Wan L, Zhang Z, Zhang C, Qin X, Xiao M, Ye D, Liu Y, Han Z, Wang S, Mao L, Wei W, Chen W. A covalently bound inhibitor triggers EZH2 degradation through CHIP-mediated ubiquitination. EMBO J. 2017 May 2;36(9):1243-1260. doi: 10.15252/embj.201694058. Epub 2017 Mar 20. PubMed PMID: 28320739; PubMed Central PMCID: PMC5412902. 6: Yu XJ, Zhao Q, Wang XB, Zhang JX, Wang XB. Gambogenic acid induces proteasomal degradation of CIP2A and sensitizes hepatocellular carcinoma to anticancer agents. Oncol Rep. 2016 Dec;36(6):3611-3618. doi: 10.3892/or.2016.5188. Epub 2016 Oct 20. PubMed PMID: 27779687. 7: Lin T, Huang X, Wang Y, Zhu T, Luo Q, Wang X, Zhou K, Cheng H, Peng D, Chen W. Long circulation nanostructured lipid carriers for gambogenic acid: formulation design, characterization, and pharmacokinetic. Xenobiotica. 2017 Sep;47(9):793-799. doi: 10.1080/00498254.2016.1229084. Epub 2016 Dec 5. PubMed PMID: 27618478. 8: Zhang W, Zhang M, Wang Z, Cheng Y, Liu H, Zhou Z, Han B, Chen B, Yao H, Chao J. Neogambogic acid prevents silica-induced fibrosis via inhibition of high-mobility group box 1 and MCP-1-induced protein 1. Toxicol Appl Pharmacol. 2016 Oct 15;309:129-40. doi: 10.1016/j.taap.2016.09.003. Epub 2016 Sep 9. PubMed PMID: 27616297. 9: Yu X, Zhao Q, Zhang H, Fan C, Zhang X, Xie Q, Xu C, Liu Y, Wu X, Han Q, Zhang H. Gambogenic acid inhibits LPS-simulated inflammatory response by suppressing NF-κB and MAPK in macrophages. Acta Biochim Biophys Sin (Shanghai). 2016 May;48(5):454-61. doi: 10.1093/abbs/gmw021. Epub 2016 Mar 29. PubMed PMID: 27025602; PubMed Central PMCID: PMC4888363. 10: Xu M, Fu W, Zhang B, Tan H, Xiu Y, Xu H. Combinative application of pH-zone-refining and conventional high-speed counter-current chromatography for preparative separation of caged polyprenylated xanthones from gamboge. J Sep Sci. 2016 Feb;39(3):559-65. doi: 10.1002/jssc.201500996. Epub 2015 Dec 21. PubMed PMID: 26608681. 11: Huang P, Yang LL, Wang CY, Chen JP, Wang SS, Wang SJ, Chen YJ, Wang DL, Huang HP. Preparation and Characterization of Folate Targeting Magnetic Nanomedicine Loaded with Gambogenic Acid. J Nanosci Nanotechnol. 2015 Jul;15(7):4774-83. PubMed PMID: 26373037. 12: Chen F, Zhang XH, Hu XD, Zhang W, Lou ZC, Xie LH, Liu PD, Zhang HQ. Enhancement of radiotherapy by ceria nanoparticles modified with neogambogic acid in breast cancer cells. Int J Nanomedicine. 2015 Aug 14;10:4957-69. doi: 10.2147/IJN.S82980. eCollection 2015. PubMed PMID: 26316742; PubMed Central PMCID: PMC4542556. 13: Yuan H, Li X, Zhang C, Pan W, Liang Y, Chen Y, Chen W, Liu L, Wang X. Nanosuspensions as delivery system for gambogenic acid: characterization and in vitro/in vivo evaluation. Drug Deliv. 2016 Oct;23(8):2772-2779. Epub 2015 Aug 18. PubMed PMID: 26292058. 14: Luo Q, Lin T, Zhang CY, Zhu T, Wang L, Ji Z, Jia B, Ge T, Peng D, Chen W. A novel glyceryl monoolein-bearing cubosomes for gambogenic acid: Preparation, cytotoxicity and intracellular uptake. Int J Pharm. 2015 Sep 30;493(1-2):30-9. doi: 10.1016/j.ijpharm.2015.07.036. Epub 2015 Jul 21. PubMed PMID: 26209071. 15: He Y, Ding J, Lin Y, Li J, Shi Y, Wang J, Zhu Y, Wang K, Hu X. Gambogenic acid alters chemosensitivity of breast cancer cells to Adriamycin. BMC Complement Altern Med. 2015 Jun 12;15:181. doi: 10.1186/s12906-015-0710-8. PubMed PMID: 26066793; PubMed Central PMCID: PMC4486132. 16: Tan YJ, Zhang X, Cheng H, Li QL. [Apoptosis of melanoma B16 cells induced by gambogenic acid]. Zhong Yao Cai. 2014 Mar;37(3):469-73. Chinese. PubMed PMID: 25174115. 17: Hua X, Liang C, Dong L, Qu X, Zhao T. Simultaneous determination and pharmacokinetic study of gambogic acid and gambogenic acid in rat plasma after oral administration of Garcinia hanburyi extracts by LC-MS/MS. Biomed Chromatogr. 2015 Apr;29(4):545-51. doi: 10.1002/bmc.3311. Epub 2014 Aug 27. PubMed PMID: 25159917. 18: Cheng H, Zhang X, Su JJ, Li QL. [Study of gambogenic acid-induced apoptosis of melanoma B16 cells through PI3K/Akt/mTOR signaling pathways]. Zhongguo Zhong Yao Za Zhi. 2014 May;39(9):1666-9. Chinese. PubMed PMID: 25095381. 19: Wang XC, Zhu GQ, Cheng H, Li QL. [Gambogenic acid induces mitochondria-dependent apoptosis in human gastric carcinoma cell line]. Zhong Yao Cai. 2014 Jan;37(1):95-9. Chinese. PubMed PMID: 25090714. 20: Su J, Cheng H, Zhang D, Wang M, Xie C, Hu Y, Chang HC, Li Q. Synergistic effects of 5-fluorouracil and gambogenic acid on A549 cells: activation of cell death caused by apoptotic and necroptotic mechanisms via the ROS-mitochondria pathway. Biol Pharm Bull. 2014;37(8):1259-68. PubMed PMID: 25087947.