Synonym
Desacetylcinobufagin; Cinobufagin, deacetyl- (6CI); Deacetylcinobufagin; NSC 234203; NSC234203; NSC-234203;
IUPAC/Chemical Name
3-beta,16-beta-Dihydroxy-14,15-beta-epoxy-5-beta-bufa-20,22-dienolide
InChi Key
IXZHDDUFQVXHIL-UOAIQHMYSA-N
InChi Code
InChI=1S/C24H32O5/c1-22-9-7-15(25)11-14(22)4-5-17-16(22)8-10-23(2)19(13-3-6-18(26)28-12-13)20(27)21-24(17,23)29-21/h3,6,12,14-17,19-21,25,27H,4-5,7-11H2,1-2H3/t14-,15+,16+,17-,19+,20-,21-,22+,23-,24-/m1/s1
SMILES Code
O=C(C=C1)OC=C1[C@H]2[C@@H](O)[C@@H]3[C@]4(O3)[C@]5([H])CC[C@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]24C
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
>3 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
2934.99.03.00
Biological target:
Desacetylcinobufagin is a natural compound used for microbial transformation.
In vitro activity:
Thus, this study examined the pro-apoptotic effect of cinobufagin and observed increased apoptotic cell numbers in 50 nM of cinobufagin-treated A375 melanoma cells (Figure 5A). Moreover, cinobufagin-induced apoptosis was abolished in ectopic LEF1 expression (Figure 5A). Consistently, decreased cell viability in cinobufagin-treated A375 and A2058 melanoma cells was reversed by ectopic LEF1 expression (Figure 5B). Overexpressed LEF1 levels were confirmed in Figure 5C. These results indicate that cinobufagin induces apoptosis by decreasing LEF1 expression in melanoma cells.
Reference: Int J Mol Sci. 2020 Sep; 21(18): 6706. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7554883/
In vivo activity:
This study further explored the mechanism by which cinobufagin inhibits STAT3 and EMT in vivo. A suspension of HCT116 cells was injected into the backs of the nude mice to build a xenograft model and thereby confirm the suppressive effects of cinobufagin on CRC cells in vivo. The growth curve of the xenograft tumor in the nude mice revealed a sharp decrease in tumor growth in the treated mice (Figure 5A) and the size of the excised tumors was reduced, particularly for cinobufagin (Figure 5B).
Reference: Am J Cancer Res. 2021; 11(1): 200–214. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7840714/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
26.0 |
64.92 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
400.52
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.
| 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:
1. Kim GH, Fang XQ, Lim WJ, Park J, Kang TB, Kim JH, Lim JH. Cinobufagin Suppresses Melanoma Cell Growth by Inhibiting LEF1. Int J Mol Sci. 2020 Sep 13;21(18):6706. doi: 10.3390/ijms21186706. PMID: 32933177; PMCID: PMC7554883.
2. Jin X, Wang J, Zou S, Xu R, Cao J, Zhang Y, Guo J, Wen X, Deng S, Zheng Y, Zhu Y, Wang F, Xu Z. Cinobufagin Triggers Defects in Spindle Formation and Cap-Dependent Translation in Liver Cancer Cells by Inhibiting the AURKA-mTOR-eIF4E Axis. Am J Chin Med. 2020;48(3):651-678. doi: 10.1142/S0192415X20500330. Epub 2020 Apr 30. PMID: 32349518.
3. Bai Y, Wang X, Cai M, Ma C, Xiang Y, Hu W, Zhou B, Zhao C, Dai X, Li X, Zhao H. Cinobufagin suppresses colorectal cancer growth via STAT3 pathway inhibition. Am J Cancer Res. 2021 Jan 1;11(1):200-214. PMID: 33520369; PMCID: PMC7840714.
4. Zhang C, Ma K, Li WY. Cinobufagin Suppresses The Characteristics Of Osteosarcoma Cancer Cells By Inhibiting The IL-6-OPN-STAT3 Pathway. Drug Des Devel Ther. 2019 Dec 4;13:4075-4090. doi: 10.2147/DDDT.S224312. PMID: 31824138; PMCID: PMC6900468.
In vitro protocol:
1. Kim GH, Fang XQ, Lim WJ, Park J, Kang TB, Kim JH, Lim JH. Cinobufagin Suppresses Melanoma Cell Growth by Inhibiting LEF1. Int J Mol Sci. 2020 Sep 13;21(18):6706. doi: 10.3390/ijms21186706. PMID: 32933177; PMCID: PMC7554883.
2. Jin X, Wang J, Zou S, Xu R, Cao J, Zhang Y, Guo J, Wen X, Deng S, Zheng Y, Zhu Y, Wang F, Xu Z. Cinobufagin Triggers Defects in Spindle Formation and Cap-Dependent Translation in Liver Cancer Cells by Inhibiting the AURKA-mTOR-eIF4E Axis. Am J Chin Med. 2020;48(3):651-678. doi: 10.1142/S0192415X20500330. Epub 2020 Apr 30. PMID: 32349518.
In vivo protocol:
1. Bai Y, Wang X, Cai M, Ma C, Xiang Y, Hu W, Zhou B, Zhao C, Dai X, Li X, Zhao H. Cinobufagin suppresses colorectal cancer growth via STAT3 pathway inhibition. Am J Cancer Res. 2021 Jan 1;11(1):200-214. PMID: 33520369; PMCID: PMC7840714.
2. Zhang C, Ma K, Li WY. Cinobufagin Suppresses The Characteristics Of Osteosarcoma Cancer Cells By Inhibiting The IL-6-OPN-STAT3 Pathway. Drug Des Devel Ther. 2019 Dec 4;13:4075-4090. doi: 10.2147/DDDT.S224312. PMID: 31824138; PMCID: PMC6900468.
1: Jiang L, Liang SC, Wang C, Ge GB, Huo XK, Qi XY, Deng S, Liu KX, Ma XC. Identifying and applying a highly selective probe to simultaneously determine the O-glucuronidation activity of human UGT1A3 and UGT1A4. Sci Rep. 2015 Apr 17;5:9627. doi: 10.1038/srep09627. PubMed PMID: 25884245; PubMed Central PMCID: PMC4401096.
2: Zhang PW, Jiang RW, Ye WC, Tian HY. [Bufadienolides from venom of Bufo bufo gargarizans]. Zhongguo Zhong Yao Za Zhi. 2014 Mar;39(5):841-5. Chinese. PubMed PMID: 25204176.
3: Zhu ZT, Den S, Wang Y, Zhao YY, Wang L, Chen HR, Liu D. Novel microbial transformation of desacetylcinobufagin by Fusarium avenaceum AS 3.4594. J Asian Nat Prod Res. 2013;15(3):294-9. doi: 10.1080/10286020.2013.763227. Epub 2013 Feb 19. PubMed PMID: 23421737.
4: 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.
5: Ning J, Wu TH, Tian Y, Wang CY, Tian G, Zhang BJ, Liu KX, Ma XC. Identification of cinobufagin metabolites in the bile of rats. Xenobiotica. 2010 Jan;40(1):48-54. doi: 10.3109/00498250903331049. PubMed PMID: 19895259.
6: Ye M, Guo D. A new bufadienolide obtained from the biotransformation of cinobufagin by Alternaria alternata. Nat Prod Res. 2008 Jan 10;22(1):26-30. PubMed PMID: 17999335.
7: Qiao L, Zhou YZ, Qi XL, Lin LH, Chen H, Pang LY, Pei YH. Biotransformation of cinobufagin by Cunninghamella elegans. J Antibiot (Tokyo). 2007 Apr;60(4):261-4. PubMed PMID: 17456977.
8: Ye M, Guo D. Substrate specificity for the 12beta-hydroxylation of bufadienolides by Alternaria alternata. J Biotechnol. 2005 May 25;117(3):253-62. Epub 2005 Apr 9. PubMed PMID: 15862355.
9: Ye M, Qu G, Guo H, Guo D. Specific 12 beta-hydroxylation of cinobufagin by filamentous fungi. Appl Environ Microbiol. 2004 Jun;70(6):3521-7. PubMed PMID: 15184152; PubMed Central PMCID: PMC427727.
10: Toma S, Morishita S, Kuronuma K, Mishima Y, Hirai Y, Kawakami M. Metabolism and pharmacokinetics of cinobufagin. Xenobiotica. 1987 Oct;17(10):1195-202. PubMed PMID: 2827395.
