Bufalin
Bufalin structure
|
Common Name | Bufalin | ||
|---|---|---|---|---|
| CAS Number | 465-21-4 | Molecular Weight | 386.524 | |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 556.6±50.0 °C at 760 mmHg | |
| Molecular Formula | C24H34O4 | Melting Point | 242 - 243ºC | |
| MSDS | Chinese USA | Flash Point | 189.0±23.6 °C | |
| Symbol |
GHS06 |
Signal Word | Danger | |
Use of BufalinBufalin a major digoxin-like immunoreactive component of the Chinese medicine Chan Su; has been shown to exert a potential for anticancer activity against various human cancer cell lines in vitro.IC50 value:Target: Anticaner natural compoundin vitro: bufalin remarkably inhibited growth in human gallbladder cancer cells by decreasing cell proliferation, inducing cell cycle arrest and apoptosis in a dose-dependent manner. Bufalin also disrupted the mitochondrial membrane potential (ΔΨm) and regulated the expression of cell cycle and apoptosis regulatory molecules. Activation of caspase-9 and the subsequent activation of caspase-3 indicated that bufalin may be inducing mitochondria apoptosis pathways [1]. bufalin suppressed the protein levels associated with DNA damage and repair, such as a DNA dependent serine/threonine protein kinase (DNA-PK), DNA repair proteins breast cancer 1, early onset (BRCA1), 14-3-3 σ (an important checkpoint keeper of DDR), mediator of DNA damage checkpoint 1 (MDC1), O6-ethylguanine-DNA methyltransferase (MGMT) and p53 (tumor suppressor protein) [2]. TNF-α significantly increased p65 translocation into nucleus (P < 0.01) and enhanced NF-κB DNA-binding activity, which were dose-dependently inhibited by bufalin. Furthermore, bufalin attenuated the TNF-α-induced interleukin-1beta (IL-1β), IL-6, and IL-8 production in RAFLSs in a concentration-dependent manner [3]. bufalin enhanced TRAIL-induced apoptosis in MCF-7 and MDA-MB-231 breast cancer cells by activating the extrinsic apoptotic pathway. Bufalin also promoted the clustering of death receptor 4 (DR4) and DR5 in aggregated lipid rafts [4].in vivo: bufalin (0.3 and 0.6 mg/kg, i.p.) potently decreased carrageenan-induced paw edema. Bufalin down regulated the expression levels of nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) during these treatments [5]. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | bufalin |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Bufalin a major digoxin-like immunoreactive component of the Chinese medicine Chan Su; has been shown to exert a potential for anticancer activity against various human cancer cell lines in vitro.IC50 value:Target: Anticaner natural compoundin vitro: bufalin remarkably inhibited growth in human gallbladder cancer cells by decreasing cell proliferation, inducing cell cycle arrest and apoptosis in a dose-dependent manner. Bufalin also disrupted the mitochondrial membrane potential (ΔΨm) and regulated the expression of cell cycle and apoptosis regulatory molecules. Activation of caspase-9 and the subsequent activation of caspase-3 indicated that bufalin may be inducing mitochondria apoptosis pathways [1]. bufalin suppressed the protein levels associated with DNA damage and repair, such as a DNA dependent serine/threonine protein kinase (DNA-PK), DNA repair proteins breast cancer 1, early onset (BRCA1), 14-3-3 σ (an important checkpoint keeper of DDR), mediator of DNA damage checkpoint 1 (MDC1), O6-ethylguanine-DNA methyltransferase (MGMT) and p53 (tumor suppressor protein) [2]. TNF-α significantly increased p65 translocation into nucleus (P < 0.01) and enhanced NF-κB DNA-binding activity, which were dose-dependently inhibited by bufalin. Furthermore, bufalin attenuated the TNF-α-induced interleukin-1beta (IL-1β), IL-6, and IL-8 production in RAFLSs in a concentration-dependent manner [3]. bufalin enhanced TRAIL-induced apoptosis in MCF-7 and MDA-MB-231 breast cancer cells by activating the extrinsic apoptotic pathway. Bufalin also promoted the clustering of death receptor 4 (DR4) and DR5 in aggregated lipid rafts [4].in vivo: bufalin (0.3 and 0.6 mg/kg, i.p.) potently decreased carrageenan-induced paw edema. Bufalin down regulated the expression levels of nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), interleukin-1β (IL-1β), interleukin-6 (IL-6), and tumor necrosis factor-α (TNF-α) during these treatments [5]. |
|---|---|
| Related Catalog | |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 556.6±50.0 °C at 760 mmHg |
| Melting Point | 242 - 243ºC |
| Molecular Formula | C24H34O4 |
| Molecular Weight | 386.524 |
| Flash Point | 189.0±23.6 °C |
| Exact Mass | 386.245697 |
| PSA | 70.67000 |
| LogP | 3.42 |
| Vapour Pressure | 0.0±3.4 mmHg at 25°C |
| Index of Refraction | 1.594 |
| InChIKey | QEEBRPGZBVVINN-ONGIWDLKSA-N |
| SMILES | CC12CCC(O)CC1CCC1C2CCC2(C)C(c3ccc(=O)oc3)CCC12O |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
|
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Symbol |
GHS06 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H300 |
| Precautionary Statements | P264-P301 + P310 |
| Personal Protective Equipment | Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges |
| Hazard Codes | T+: Very toxic; |
| Risk Phrases | R28 |
| Safety Phrases | 28-36/37-45 |
| RIDADR | UN 3462 |
| WGK Germany | 3 |
| RTECS | EI2962500 |
| Packaging Group | II |
| Hazard Class | 6.1(a) |
This table lists relevant public references with title, journal and publication metadata for this compound.
|
Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways.
Am. J. Chin. Med. 42(3) , 729-42, (2014) Bufalin is a key component of a Chinese medicine (Chan Su) and has been proved effective in killing various cancer cells. Its role in inducing DNA damage and the inhibition of the DNA damage response ... |
|
|
Hepatitis B virus efficiently infects non-adherent hepatoma cells via human sodium taurocholate cotransporting polypeptide.
Sci. Rep. 5 , 17047, (2015) Sodium taurocholate cotransporting polypeptide (NTCP) has been reported as a functional receptor for hepatitis B virus (HBV) infection. However, HBV could not efficiently infect HepG2 cells expressing... |
|
|
Reversal effect of bufalin on multidrug resistance in K562/VCR vincristine-resistant leukemia cell line.
J. Tradit. Chin. Med. 34(6) , 678-83, (2014) To probe insights into the reversal effect of bufalin on vincristine-acquired multidrug resistance (MDR) in human leukemia cell line K562/VCR.Proliferative inhibition rate and the reversal index (RI) ... |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| 3,14-dihydroxybufa-20,22-dienolide |
| (3β,5β)-3,14-Dihydroxybufa-20,22-dienolide |
| Bufalin: Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)-, |
| 3β,14β-dihydroxy-5β-bufa-20,22-dienolide |
| (3b,5b)-3,14-Dihydroxybufa-20,22-dienolide |
| Bufalin |
| MFCD00056525 |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What English synonyms does bufalin have? |
| A: English synonyms of bufalin: 3,14-dihydroxybufa-20,22-dienolide, (3β,5β)-3,14-Dihydroxybufa-20,22-dienolide, Bufalin: Bufa-20,22-dienolide, 3,14-dihydroxy-, (3b,5b)-,, 3β,14β-dihydroxy-5β-bufa-20,22-dienolide, (3b,5b)-3,14-Dihydroxybufa-20,22-dienolide, Bufalin, MFCD00056525. |
| Q: What is the melting point of bufalin? |
| A: Melting point of bufalin is 242 - 243ºC. |
| Q: What is the boiling point of bufalin? |
| A: Boiling point of bufalin is 556.6±50.0 °C at 760 mmHg. |
| Q: What is the polar surface area (PSA) of bufalin? |
| A: Polar surface area (PSA) of bufalin is 70.67000. |
| Q: What is the molecular weight of bufalin? |
| A: Molecular weight of bufalin is 386.524. |
| Q: What is the English name of bufalin? |
| A: The English name of bufalin is bufalin. |
| Q: What is the safety information for bufalin? |
| A: Safety information for bufalin: 28-36/37-45. |
| Q: What is the CAS number of bufalin? |
| A: CAS number of bufalin is 465-21-4. |
| Q: What is the SMILES notation of bufalin? |
| A: SMILES notation of bufalin is CC12CCC(O)CC1CCC1C2CCC2(C)C(c3ccc(=O)oc3)CCC12O. |
| Q: What is the InChIKey of bufalin? |
| A: InChIKey of bufalin is QEEBRPGZBVVINN-ONGIWDLKSA-N. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| BioBioPha |
| naturewill |