Cinobufagin
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MedKoo CAT#: 329654

CAS#: 470-37-1

Description: Cinobufagin is a cardiotoxic bufanolide steroid secreted by the Asiatic toad Bufo gargarizans. It has similar effects to digitalis and is used in traditional Chinese medicine. Cinobufagin has been shown to have clinical applications in cancer treatment as well as immunomodulatory and analgesic properties. Cinobufagin induces apoptosis of osteosarcoma cells through inactivation of Notch signaling. Cinobufagin induces autophagy-mediated cell death in human osteosarcoma U2OS cells through the ROS/JNK/p38 signaling pathway.

Chemical Structure

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Cinobufagin
CAS# 470-37-1
Instruction

Theoretical Analysis

MedKoo Cat#: 329654
Name: Cinobufagin
CAS#: 470-37-1
Chemical Formula: C26H34O6
Exact Mass: 442.24
Molecular Weight: 442.552
Elemental Analysis: C, 70.56; H, 7.74; O, 21.69

Price and Availability

Size Price Availability Quantity
25mg USD 550 2 weeks
100mg USD 1450 2 weeks
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Synonym: Cinobufagin; Cinobufagine; Cino-bufagin; NSC90325; 14,15β-Epoxy-3β,16β-dihydroxy-5β,20(22)-bufadienolide 16-acetate.

IUPAC/Chemical Name: (1R,2R,2aR,3aS,3bS,5aR,7S,9aS,9bR,11aS)-7-hydroxy-9a,11a-dimethyl-1-(2-oxo-2H-pyran-4-yl)hexadecahydronaphtho[1',2':6,7]indeno[1,7a-b]oxiren-2-yl acetate

InChi Key: BNZAGRNEEMGADQ-CTAZGAKUSA-N

InChi Code: InChI=1S/C26H34O6/c1-14(27)31-22-21(15-8-11-30-20(29)12-15)25(3)10-7-18-19(26(25)23(22)32-26)5-4-16-13-17(28)6-9-24(16,18)2/h8,11-12,16-19,21-23,28H,4-7,9-10,13H2,1-3H3/t16-,17+,18-,19+,21+,22-,23-,24+,25+,26-/m1/s1

SMILES Code: CC(O[C@@H]([C@@]1([H])O[C@]123)[C@H](C(C=CO4)=CC4=O)[C@]2(C)CC[C@]5([H])[C@]3([H])CC[C@]6([H])C[C@@H](O)CC[C@@]65C)=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: Cinobufagin, as well as other bufadienolides, can be isolated from the traditional Chinese medicine called ChanSu. ChanSu is made from a multitude of chemicals present in Bufo gargarizans secretions. Resibufogenin can be eluted out with silica gel column chromatography, using a 5:1 ratio of cyclohexane to acetone for the solvent in the mobile phase. Subsequently, cinobufagin and bufalin can be separated and purified using an HPLC column with a 72:28 methanol to water solvent. Yang et al. confirmed this method of isolation for cinobufagin with Proton NMR.

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 442.55 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: Cao Y, Yu L, Dai G, Zhang S, Zhang Z, Gao T, Guo W. Cinobufagin induces apoptosis of osteosarcoma cells through inactivation of Notch signaling. Eur J Pharmacol. 2017 Jan 5;794:77-84. doi: 10.1016/j.ejphar.2016.11.016. Epub 2016 Nov 12. PubMed PMID: 27845066.

2: Ma K, Zhang C, Huang MY, Li WY, Hu GQ. Cinobufagin induces autophagy-mediated cell death in human osteosarcoma U2OS cells through the ROS/JNK/p38 signaling pathway. Oncol Rep. 2016 Jul;36(1):90-8. doi: 10.3892/or.2016.4782. Epub 2016 Apr 28. PubMed PMID: 27176794; PubMed Central PMCID: PMC4899018.

3: Chen T, Yuan S, Wan XN, Zhan L, Yu XQ, Zeng JH, Li H, Zhang W, Hu XY, Ye YF, Hu W. Chinese herb cinobufagin-reduced cancer pain is associated with increased peripheral opioids by invaded CD3/4/8 lymphocytes. Oncotarget. 2017 Feb 14;8(7):11425-11441. doi: 10.18632/oncotarget.14005. PubMed PMID: 28002791; PubMed Central PMCID: PMC5355276.

4: Cao F, Kang X, Wang L. [Effects of cinobufagin on apoptosis in U-2OS osteosarcomas cells]. Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2014 Mar;28(3):349-53. Chinese. PubMed PMID: 24844018.

5: Cao W, Chen Y, Yuan L, He JJ. [Determination of protein binding rates of cinobufagin and resibufogenin with different plasmas by HPLC]. Yao Xue Xue Bao. 2012 Sep;47(9):1200-4. Chinese. PubMed PMID: 23227551.

6: Yin JQ, Wen L, Wu LC, Gao ZH, Huang G, Wang J, Zou CY, Tan PX, Yong BC, Jia Q, Shen JN. The glycogen synthase kinase-3β/nuclear factor-kappa B pathway is involved in cinobufagin-induced apoptosis in cultured osteosarcoma cells. Toxicol Lett. 2013 Apr 12;218(2):129-36. doi: 10.1016/j.toxlet.2012.11.006. Epub 2012 Nov 16. PubMed PMID: 23164673.

7: Kau MM, Wang JR, Tsai SC, Yu CH, Wang PS. Inhibitory effect of bufalin and cinobufagin on steroidogenesis via the activation of ERK in human adrenocortical cells. Br J Pharmacol. 2012 Mar;165(6):1868-76. doi: 10.1111/j.1476-5381.2011.01671.x. PubMed PMID: 21913902; PubMed Central PMCID: PMC3372836.

8: He X, Hu H, Wu Y, Zeng X. Urinary metabolites of cinobufagin in rats and their antiproliferative activities. Nat Prod Res. 2012;26(6):489-99. doi: 10.1080/14786419.2010.510798. Epub 2011 Jun 28. PubMed PMID: 21711170.

9: Xing J, Chen L, Song J, Guo C, Yang G, Zeng A. Separation and determination of resibufogenin and cinobufagin in Chansu using reversed-phase liquid chromatography with γ-cyclodextrin as mobile-phase modifier. J Sep Sci. 2012 Aug;35(15):1884-92. doi: 10.1002/jssc.201200058. Epub 2012 May 24. PubMed PMID: 22623502.

10: Qi F, Inagaki Y, Gao B, Cui X, Xu H, Kokudo N, Li A, Tang W. Bufalin and cinobufagin induce apoptosis of human hepatocellular carcinoma cells via Fas- and mitochondria-mediated pathways. Cancer Sci. 2011 May;102(5):951-8. doi: 10.1111/j.1349-7006.2011.01900.x. Epub 2011 Feb 28. PubMed PMID: 21288283.

11: Chen T, Hu W, He H, Gong Z, Wang J, Yu X, Ai T, Zhan L. A Study on the Mechanism of Cinobufagin in the Treatment of Paw Cancer Pain by Modulating Local β -Endorphin Expression In Vivo. Evid Based Complement Alternat Med. 2013;2013:851256. doi: 10.1155/2013/851256. Epub 2013 Sep 25. PubMed PMID: 24187573; PubMed Central PMCID: PMC3800629.

12: Wu SC, Yi PF, Guo X, Zhang LY, Xu DX, Fu YX, Cui ZQ, Shen HQ, Wei XB, Fu BD. Cinobufagin enhances the protective efficacy of formalin-inactivated Salmonella typhimurium vaccine through Th1 immune response. Microb Pathog. 2016 Oct;99:264-270. doi: 10.1016/j.micpath.2016.08.036. Epub 2016 Aug 26. PubMed PMID: 27574776.

13: Zhu L, Chen Y, Wei C, Yang X, Cheng J, Yang Z, Chen C, Ji Z. Anti-proliferative and pro-apoptotic effects of cinobufagin on human breast cancer MCF-7 cells and its molecular mechanism. Nat Prod Res. 2017 Apr 17:1-5. doi: 10.1080/14786419.2017.1315575. [Epub ahead of print] PubMed PMID: 28412840.

14: Baek SH, Kim C, Lee JH, Nam D, Lee J, Lee SG, Chung WS, Jang HJ, Kim SH, Ahn KS. Cinobufagin exerts anti-proliferative and pro-apoptotic effects through the modulation ROS-mediated MAPKs signaling pathway. Immunopharmacol Immunotoxicol. 2015 Jun;37(3):265-73. doi: 10.3109/08923973.2015.1027916. Epub 2015 May 18. PubMed PMID: 25982794.

15: Wang ZJ, Sun L, Heinbockel T. Resibufogenin and cinobufagin activate central neurons through an ouabain-like action. PLoS One. 2014 Nov 24;9(11):e113272. doi: 10.1371/journal.pone.0113272. eCollection 2014. PubMed PMID: 25420080; PubMed Central PMCID: PMC4242513.

16: Wang W, Liu MD, Yan YY, Ye Y, Zhao JH, Xiong H, Xiao M, Liao LC. [Determination of cinobufagin and resibufogenin in liver tissue by HPLC-MS/MS]. Fa Yi Xue Za Zhi. 2013 Aug;29(4):268-72. Chinese. PubMed PMID: 24350542.

17: Ma XC, Xin X, Zhang BJ, Deng S, Yao JH, Wang CY, Cui J, Tian Y, Liu KX. Efficient isolation and purification of five products from microbial biotransformation of cinobufagin by high-speed counter-current chromatography. J Sep Sci. 2010 Aug;33(15):2272-7. doi: 10.1002/jssc.201000212. PubMed PMID: 20574960.

18: Dong YQ, Ma WL, Gu JB, Zheng WL. [Effect of cinobufagin on nuclear factor-kappaB pathway in HepG2 cells]. Nan Fang Yi Ke Da Xue Xue Bao. 2010 Jan;30(1):137-9. Chinese. PubMed PMID: 20118004.

19: Lu XS, Qiao YB, Li Y, Yang B, Chen MB, Xing CG. Preclinical study of cinobufagin as a promising anti-colorectal cancer agent. Oncotarget. 2017 Jan 3;8(1):988-998. doi: 10.18632/oncotarget.13519. PubMed PMID: 27894091; PubMed Central PMCID: PMC5352212.

20: Cui X, Inagaki Y, Xu H, Wang D, Qi F, Kokudo N, Fang D, Tang W. Anti-hepatitis B virus activities of cinobufacini and its active components bufalin and cinobufagin in HepG2.2.15 cells. Biol Pharm Bull. 2010;33(10):1728-32. PubMed PMID: 20930383.