Arenobufagin

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MedKoo CAT#: 540025

CAS#: 464-74-4

Description: Arenobufagin is a VEGFR2 inhibitor and cardiovascular Na/K ATPase found in Bufo arenarum. It induces autophagy and apoptosis in hepatocellular carcinoma cells and suppresses angiogenesis.

Chemical Structure

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Arenobufagin
CAS# 464-74-4
Instruction

Theoretical Analysis

MedKoo Cat#: 540025
Name: Arenobufagin
CAS#: 464-74-4
Chemical Formula: C24H32O6
Exact Mass: 416.22
Molecular Weight: 416.510
Elemental Analysis: C, 69.21; H, 7.74; O, 23.05

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Arenobufagin; HY-N0876; CS-3693; FT-0698437; HYN0876; CS3693; FT0698437; HY N0876; CS 3693; FT 0698437

IUPAC/Chemical Name: 5-((3S,5R,8R,9S,10S,11S,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one

InChi Key: JGDCRWYOMWSTFC-AZGSIFHYSA-N

InChi Code: InChI=1S/C24H32O6/c1-22-9-7-15(25)11-14(22)4-5-17-19(22)20(27)21(28)23(2)16(8-10-24(17,23)29)13-3-6-18(26)30-12-13/h3,6,12,14-17,19-20,25,27,29H,4-5,7-11H2,1-2H3/t14-,15+,16-,17-,19-,20+,22+,23+,24+/m1/s1

SMILES Code: O=C(C=C1)OC=C1[C@H]([C@]23C)CC[C@]2(O)[C@]4([H])CC[C@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])[C@H](O)C3=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 416.51 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Deng LJ, Peng QL, Wang LH, Xu J, Liu JS, Li YJ, Zhuo ZJ, Bai LL, Hu LP, Chen WM, Ye WC, Zhang DM. Arenobufagin intercalates with DNA leading to G2 cell cycle arrest via ATM/ATR pathway. Oncotarget. 2015 Oct 27;6(33):34258-75. doi: 10.18632/oncotarget.5545. PubMed PMID: 26485758; PubMed Central PMCID: PMC4741450.

2: Xu W, Jing L, Wang Q, Lin CC, Chen X, Diao J, Liu Y, Sun X. Bax-PGAM5L-Drp1 complex is required for intrinsic apoptosis execution. Oncotarget. 2015 Oct 6;6(30):30017-34. doi: 10.18632/oncotarget.5013. PubMed PMID: 26356820; PubMed Central PMCID: PMC4745779.

3: Li M, Wu S, Liu Z, Zhang W, Xu J, Wang Y, Liu J, Zhang D, Tian H, Li Y, Ye W. Arenobufagin, a bufadienolide compound from toad venom, inhibits VEGF-mediated angiogenesis through suppression of VEGFR-2 signaling pathway. Biochem Pharmacol. 2012 May 1;83(9):1251-60. doi: 10.1016/j.bcp.2012.01.023. Epub 2012 Jan 24. PubMed PMID: 22305746.

4: Liu JS, Zhang DM, Chen MF, Li MM, Luo QD, Kurihara H, Ye WC. [Anti-angiogenetic effect of arenobufagin in vitro and in vivo]. Yao Xue Xue Bao. 2011 May;46(5):527-33. Chinese. PubMed PMID: 21800539.

5: Cruz Jdos S, Matsuda H. Depressive effects of arenobufagin on the delayed rectifier K+ current of guinea-pig cardiac myocytes. Eur J Pharmacol. 1994 Feb 15;266(3):317-25. PubMed PMID: 8174614.

6: Lu GD, Zhou J, Ma HY, Wu DK, Qian DW, Tang YP, Hong M, Hua YQ, Duan JA. [Analysis on competitive interaction between arenobufagin and verapamil hydrochloride with serum albumin]. Zhong Xi Yi Jie He Xue Bao. 2011 Jul;9(7):768-74. Chinese. PubMed PMID: 21749828.

7: Zhang DM, Liu JS, Deng LJ, Chen MF, Yiu A, Cao HH, Tian HY, Fung KP, Kurihara H, Pan JX, Ye WC. Arenobufagin, a natural bufadienolide from toad venom, induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway. Carcinogenesis. 2013 Jun;34(6):1331-42. doi: 10.1093/carcin/bgt060. Epub 2013 Feb 7. PubMed PMID: 23393227.

8: Yue Q, Zhen H, Huang M, Zheng X, Feng L, Jiang B, Yang M, Wu W, Liu X, Guo D. Proteasome Inhibition Contributed to the Cytotoxicity of Arenobufagin after Its Binding with Na, K-ATPase in Human Cervical Carcinoma HeLa Cells. PLoS One. 2016 Jul 18;11(7):e0159034. doi: 10.1371/journal.pone.0159034. eCollection 2016. PubMed PMID: 27428326; PubMed Central PMCID: PMC4948917.

9: Li G, Han W, Jiang W, Zhang D, Ye W, Chen X, Ma A. Quantitative determination of arenobufagin in rat plasma by ultra fast liquid chromatography-tandem mass spectrometry and its application in a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Nov 15;939:86-91. doi: 10.1016/j.jchromb.2013.09.019. Epub 2013 Sep 23. PubMed PMID: 24113236.

10: Perera Córdova WH, Leitão SG, Cunha-Filho G, Bosch RA, Alonso IP, Pereda-Miranda R, Gervou R, Touza NA, Quintas LE, Noël F. Bufadienolides from parotoid gland secretions of Cuban toad Peltophryne fustiger (Bufonidae): Inhibition of human kidney Na(+)/K(+)-ATPase activity. Toxicon. 2016 Feb;110:27-34. doi: 10.1016/j.toxicon.2015.11.015. Epub 2015 Nov 23. PubMed PMID: 26615828.

11: Cruz Jdos S, Matsuda H. Arenobufagin, a compound in toad venom, blocks Na(+)-K+ pump current in cardiac myocytes. Eur J Pharmacol. 1993 Aug 3;239(1-3):223-6. PubMed PMID: 8223897.

12: Han LY, Si N, Liu JQ, Zhao HY, Yang J, Bian BL, Wang HJ. [Chemical constituents of bufadienolides in cinobufacino injection]. Yao Xue Xue Bao. 2014 Nov;49(11):1574-7. Chinese. PubMed PMID: 25757284.

13: Yuan B, He J, Kisoh K, Hayashi H, Tanaka S, Si N, Zhao HY, Hirano T, Bian B, Takagi N. Effects of active bufadienolide compounds on human cancer cells and CD4+CD25+Foxp3+ regulatory T cells in mitogen-activated human peripheral blood mononuclear cells. Oncol Rep. 2016 Sep;36(3):1377-84. doi: 10.3892/or.2016.4946. Epub 2016 Jul 18. PubMed PMID: 27431260.

14: Wang T, Mu L, Jin H, Zhang P, Wang Y, Ma X, Pan J, Miao J, Yuan Y. The effects of bufadienolides on HER2 overexpressing breast cancer cells. Tumour Biol. 2016 Jun;37(6):7155-63. doi: 10.1007/s13277-015-4381-3. Epub 2015 Dec 12. PubMed PMID: 26662961.

15: Huang H, Yang Y, Lv C, Chang W, Peng C, Wang S, Ge G, Han L, Zhang W, Liu R. Pharmacokinetics and tissue distribution of five bufadienolides from the Shexiang Baoxin Pill following oral administration to mice. J Ethnopharmacol. 2015 Feb 23;161:175-85. doi: 10.1016/j.jep.2014.07.056. Epub 2014 Sep 6. PubMed PMID: 25196822.

16: Delebinski CI, Georgi S, Kleinsimon S, Twardziok M, Kopp B, Melzig MF, Seifert G. Analysis of proliferation and apoptotic induction by 20 steroid glycosides in 143B osteosarcoma cells in vitro. Cell Prolif. 2015 Oct;48(5):600-10. doi: 10.1111/cpr.12208. Epub 2015 Aug 24. PubMed PMID: 26300346.

17: Li BJ, Tian HY, Zhang DM, Lei YH, Wang L, Jiang RW, Ye WC. Bufadienolides with cytotoxic activity from the skins of Bufo bufo gargarizans. Fitoterapia. 2015 Sep;105:7-15. doi: 10.1016/j.fitote.2015.05.013. Epub 2015 May 27. PubMed PMID: 26022446.

18: Chen H, Meng YH, Guo DA, Liu X, Liu JH, Hu LH. New cytotoxic 19-norbufadienolide and bufogargarizin isolated from Chan Su. Fitoterapia. 2015 Jul;104:1-6. doi: 10.1016/j.fitote.2015.05.011. Epub 2015 May 15. PubMed PMID: 25987318.

19: Han L, Wang H, Si N, Ren W, Gao B, Li Y, Yang J, Xu M, Zhao H, Bian B. Metabolites profiling of 10 bufadienolides in human liver microsomes and their cytotoxicity variation in HepG2 cell. Anal Bioanal Chem. 2016 Apr;408(10):2485-95. doi: 10.1007/s00216-016-9345-y. Epub 2016 Feb 11. PubMed PMID: 26869342.

20: Chen D, Lin S, Xu W, Huang M, Chu J, Xiao F, Lin J, Peng J. Qualitative and Quantitative Analysis of the Major Constituents in Shexiang Tongxin Dropping Pill by HPLC-Q-TOF-MS/MS and UPLC-QqQ-MS/MS. Molecules. 2015 Oct 14;20(10):18597-619. doi: 10.3390/molecules201018597. PubMed PMID: 26473821.