TelocinobufaginCAS# 472-26-4 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 472-26-4 | SDF | Download SDF |
PubChem ID | 259991 | Appearance | Powder |
Formula | C24H34O5 | M.Wt | 402.52 |
Type of Compound | Steroids | Storage | Desiccate at -20°C |
Synonyms | Telobufotoxin; Telocinobufogenin | ||
Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
Chemical Name | 5-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyran-2-one | ||
SMILES | CC12CCC(CC1(CCC3C2CCC4(C3(CCC4C5=COC(=O)C=C5)O)C)O)O | ||
Standard InChIKey | PBSOJKPTQWWJJD-ZBDZJSKLSA-N | ||
Standard InChI | InChI=1S/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18-,19+,21+,22+,23-,24-/m0/s1 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Telocinobufagin is a novel endogenous digitalis, it shows a reversible local anesthetic action, similar to BUPI, however, without cardiac toxicity in vitro. Telocinobufagin has antimicrobial, potential immune system regulatory effects, it could be developed as a novel immunotherapeutic agent to treat and other immune-mediated diseases, and it may become a new immunomodulatory agent in many regions. |
Targets | IFN-γ | gp120/CD4 | IL Receptor | TNF-α | PARP | Bcl-2/Bax | Caspase | p53 | IkB | AChR | Antifection | IKK |
In vitro | The effects of telocinobufagin isolated from Chan Su on the activation and cytokine secretion of immunocytes in vitro.[Pubmed: 19709323]Fundam Clin Pharmacol. 2009 Aug;23(4):457-64.
Many traditional Chinese medicines have been used as immunomodulators that act as either immunosuppressants or immunostimulators. Recently, our lab successfully isolated a monomer Telocinobufagin (TCB) from the chloroform extract of Chan Su (Venenum Bufonis). In the present paper, we evaluated the immunomodulatory effects of this compound in vitro. Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens.[Pubmed: 15804527]Toxicon. 2005 May;45(6):777-82.The increase in the emergence of antibiotic-resistant microorganisms and difficult to treat infections caused by these pathogens stimulate research aiming the identification of novel antimicrobials. Skin secretion of amphibian contains a large number of biologically active compounds, including compounds that performance defense mechanisms against microorganisms. Pharmacological effects of telocinobufagin, a bufodienolide originated from the parotoid glands of Bufo paracnemis: comparative study with local anesthetic bupivacaine.[Reference: WebLink]Universidade Federal do Ceará, 2004.5.26.The pharmacological effects of Telocinobufagin (TCB), a bufadienolide extracted from Bufo paracnemis parotoid glands by HPLC, were compared to that induced by bupivacaine (BUPI). |
In vivo | Telocinobufagin enhances the Th1 immune response and protects against Salmonella typhimurium infection.[Pubmed: 25687199]Int Immunopharmacol. 2015 Apr;25(2):353-62.Ideal potential vaccine adjuvants to stimulate a Th1 immune response are urgently needed to control intracellular infections in clinical applications. Telocinobufagin (TBG), an active component of Venenum bufonis, exhibits immunomodulatory activity. Therefore, we investigated whether TBG enhances the Th1 immune response to ovalbumin (OVA) and formalin-inactivated Salmonella typhimurium (FIST) in mice. |
Kinase Assay | Mechanism of colon cancer cell apoptosis induced by telocinobufagin: role of oxidative stress and apoptosis pathway.[Pubmed: 27435769]Nan Fang Yi Ke Da Xue Xue Bao. 2016 Jun 20;36(7):921-6.To investigate the effects of Telocinobufagin on viability and apoptosis of colorectal cancer (CRC) cells and explore the mechanism of Telocinobufagin-induced apoptosis.
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Structure Identification | Clin Biochem. 2005 Jan;38(1):36-45.A novel endogenous digitalis, telocinobufagin, exhibits elevated plasma levels in patients with terminal renal failure.[Pubmed: 15607315]There are several potential endogenous digitalis-like factors (EDLF) in mammalian body fluids, and marinobufagenin (MBG) may be the most potent EDLF. Improved assays are needed to confirm the potency of these metabolites. In the present study, we have identified MBG and Telocinobufagin (TCB) in human plasma by high-resolution mass spectrometry (MS) and nuclear magnetic resonance (NMR).
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Telocinobufagin Dilution Calculator
Telocinobufagin Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.4843 mL | 12.4217 mL | 24.8435 mL | 49.687 mL | 62.1087 mL |
5 mM | 0.4969 mL | 2.4843 mL | 4.9687 mL | 9.9374 mL | 12.4217 mL |
10 mM | 0.2484 mL | 1.2422 mL | 2.4843 mL | 4.9687 mL | 6.2109 mL |
50 mM | 0.0497 mL | 0.2484 mL | 0.4969 mL | 0.9937 mL | 1.2422 mL |
100 mM | 0.0248 mL | 0.1242 mL | 0.2484 mL | 0.4969 mL | 0.6211 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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Telocinobufagin is one of anti-hepatoma constituent in Venenum Bufonis.
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Telocinobufagin enhances the Th1 immune response and protects against Salmonella typhimurium infection.[Pubmed:25687199]
Int Immunopharmacol. 2015 Apr;25(2):353-62.
Ideal potential vaccine adjuvants to stimulate a Th1 immune response are urgently needed to control intracellular infections in clinical applications. Telocinobufagin (TBG), an active component of Venenum bufonis, exhibits immunomodulatory activity. Therefore, we investigated whether TBG enhances the Th1 immune response to ovalbumin (OVA) and formalin-inactivated Salmonella typhimurium (FIST) in mice. TBG augmented serum OVA- and FIST-specific IgG and IgG2a and the production of IFNgamma by antigen-restimulated splenocytes. TBG also dramatically enhanced splenocyte proliferative responses to concanavalin A, lipopolysaccharide, and OVA and substantially increased T-bet mRNA levels and the CD3(+)/CD3(+)CD4(+)/CD3(+)CD8(+) phenotype in splenocytes from OVA-immunized mice. In in vivo protection studies, TBG significantly decreased the bacterial burdens in the spleen and prolonged the survival time of FIST-immunized mice challenged with live S. typhimurium. In vivo neutralization of IFNgamma with anti-IFNgamma mAbs led to a significant reduction in FIST-specific IgG2a and IFNgamma levels and in anti-Salmonella effect in TBG/FIST-immunized mice. In conclusion, these results suggest that TBG enhances a Th1 immune response to control intracellular infections.
A novel endogenous digitalis, telocinobufagin, exhibits elevated plasma levels in patients with terminal renal failure.[Pubmed:15607315]
Clin Biochem. 2005 Jan;38(1):36-45.
BACKGROUND AND OBJECTIVES: There are several potential endogenous digitalis-like factors (EDLF) in mammalian body fluids, and marinobufagenin (MBG) may be the most potent EDLF. Improved assays are needed to confirm the potency of these metabolites. In the present study, we have identified MBG and Telocinobufagin (TCB) in human plasma by high-resolution mass spectrometry (MS) and nuclear magnetic resonance (NMR). METHODS AND RESULTS: The high-resolution MS analysis revealed the molecular masses of TCB and MBG to be the same as their respective theoretical values. Using a tandem mass spectrometer, the mass-charge ratio for TCB was determined to be 403.2 for the parent ion and 349.2 for the daughter ion. The mass-charge ratio for MBG was m/z 383.2 and m/z 401.2. The NMR study revealed that the signals for MBG and TCB were the same as those obtained by MS analysis. In human blood, MBG and TCB were also identified by liquid chromatography (LC) as well as MS. In the LC/MS assay, proscillaridin A was used as an internal standard. The plasma was pretreated with Sep-Pak C18, and then 50 microL was applied to the C8 high-performance liquid chromatography (HPLC) column. The mean plasma concentration of MBG in healthy volunteers (0.94 +/- 0.28 ng/mL) was significantly lower than that in patients undergoing regular hemodialysis (3.81 +/- 1.92 ng/mL). The concentration of TCB in the healthy volunteers (1.80 +/- 0.55 ng/mL) was also significantly lower than that in patients with terminal renal failure (6.86 +/- 4.30 ng/mL). CONCLUSION: These results indicate that the major EDLF is TCB because its plasma concentration is the highest among the reported endogenous digitalis candidates.
The effects of telocinobufagin isolated from Chan Su on the activation and cytokine secretion of immunocytes in vitro.[Pubmed:19709323]
Fundam Clin Pharmacol. 2009 Aug;23(4):457-64.
Many traditional Chinese medicines have been used as immunomodulators that act as either immunosuppressants or immunostimulators. Recently, our lab successfully isolated a monomer Telocinobufagin (TCB) from the chloroform extract of Chan Su (Venenum Bufonis). In the present paper, we evaluated the immunomodulatory effects of this compound in vitro. We found that TCB significantly stimulates splenocyte proliferation when administered alone or in combination with polyclonal T-cell mitogens concanavalin A (Con A) and lipopolysaccharide. Telocinobufagin markedly enhances natural killer cell and peritoneal macrophage activation. Telocinobufagin increases the percentage of CD4, CD8 positive cells within a population of splenocytes. Moreover, we found that the level of several Th1 cytokines, including interleukin-2 (IL-2), interleukin-12 (IL-12), interferon-gamma (IFN-gamma) and tumor necrosis factor-alpha (TNF-alpha), are significantly increased after TCB treatment, while the level of the Th2 cytokine interleukin-4 (IL-4) is significantly decreased. As a result, the ratio of Th1/Th2 is significantly increased. Taken together, these results indicate that TCB has potential immune system regulatory effects and suggest that this compound could be developed as a novel immunotherapeutic agent to treat cancer and other immune-mediated diseases, and it may become a new immunomodulatory agent in many regions.
[Mechanism of colon cancer cell apoptosis induced by telocinobufagin: role of oxidative stress and apoptosis pathway].[Pubmed:27435769]
Nan Fang Yi Ke Da Xue Xue Bao. 2016 Jun 20;36(7):921-6.
OBJECTIVE: To investigate the effects of Telocinobufagin on viability and apoptosis of colorectal cancer (CRC) cells and explore the mechanism of Telocinobufagin-induced apoptosis. METHODS: MTT assay was performed to detect the viability of CRC cells exposed to Telocinobufagin. Nuclear staining with Hoechst 33342 and flow cytometry were used to analyze the cell death of CRC cells. Expressions of proteins related with cell apoptosis and oxidative stress were determined with Western blotting. RESULTS: Telocinobufagin decreased the viability of CRC cells in a time- and dose-dependent manner. The presence of karyopycnosis and apoptotic bodies together with the results of flow cytometry suggested that Telocinobufagin induced cell apoptosis to cause cell death. Western blotting showed that Telocinobufagin exposure of the cells resulted in upregulated p53 and Bax protein expressions and promoted cleavage of caspase 9 and PARP. Telocinobufagin induced phosphorylation of Bad and PARP cleavage, and suppressed phosphorylation of IKBalpha and TAK1 and expression of survivin in the cells. CONCLUSION: Telocinobufagin can decrease the viability of CRC cells by inducing cell apoptosis, which involves p53-mediated Bax activation and inhibition of the IAP pathway.
Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens.[Pubmed:15804527]
Toxicon. 2005 May;45(6):777-82.
The increase in the emergence of antibiotic-resistant microorganisms and difficult to treat infections caused by these pathogens stimulate research aiming the identification of novel antimicrobials. Skin secretion of amphibian contains a large number of biologically active compounds, including compounds that performance defense mechanisms against microorganisms. In the present work, two antimicrobial bufadienolides, Telocinobufagin (402.1609 Da) and marinobufagin (400.1515 Da), were isolated from skin secretions of the Brazilian toad Bufo rubescens. The specimens were collected in Brasilia (Distrito Federal, Brazil), the skin secretions extracted by electric stimulation, and submitted to purification by RP-HPLC. The molecular structure and mass determination were done by (1)H and (13)C NMR and mass spectrometry data, respectively. The antimicrobial activity was performed by liquid growth inhibition against Staphylococcus aureus and Escherichia coli. The minimum inhibitory concentrations of Telocinobufagin and marinobufagin were, respectively, 64.0 and 16.0 microg/mL for E. coli and both 128 microg/mL for S. aureus. Besides the antimicrobial activity both bufadienolides promoted an increase of the contraction force in isolated frog ventricle strips.