CAS Number465-21-4
Synonyms3,14-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
Molecular FormulaC24H34O4
Molecular Weight386.52
Purity≥98 (HPLC)%
Density1.2±0.1 g/cm3
Boiling Point556.6±50.0 °C at 760 mmHg
Melting Point242 - 243ºC
Appearancesolid
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 465-21-4 |
| Catalog No. | 2A-9022071 |
| Chinese Name | 蟾毒灵 |
| Synonyms | 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 |
| Molecular Formula | C24H34O4 |
| Molecular Weight | 386.52 |
| Purity | ≥98 (HPLC) |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 556.6±50.0 °C at 760 mmHg |
| Melting Point | 242 - 243ºC |
| Appearance | solid |
| Storage Condition | Store at 2-8°C in a ventilated, dry place and avoi |
| Packaging | II |
| Application | Bufalin is an important immunoactive component in Bufa venom and has been reported to have inhibitory effects on a variety of cancer cells in vitro. |
| MDL Number | MFCD00056525 |
| SMILES | O1C=C(C=CC1=O)[C@@H]2[C@@]3([C@@](C4C([C@@]5([C@@H](C[C@H](CC5)O)CC4)C)CC3)(CC2)O)C |
| InChI | 1S/C24H34O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,14,16-20,25,27H,4-5,7-13H2,1-2H3/t16-,17+,18-,19?,20?,22+,23-,24+/m1/s1 |
| InChI Key | QEEBRPGZBVVINN-ZXRSHIDQSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352211 |
| Hazard Symbols | 6.1(a) |
| MSDS | msds/22071_1_465_21_4.pdf |
| Bioactivity | 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 Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Steroids References [1]. Jiang L, et al. Bufalin induces cell cycle arrest and apoptosis in gallbladder carcinoma cells. Tumour Biol. 2014 Nov;35(11):10931-41. [2]. Wu SH, et al. Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways. Am J Chin Med. 2014;42(3):729-42. [3]. Rong X, et al. Bufalin, a bioactive component of the chinese medicine chansu, inhibits inflammation and invasion of human rheumatoid arthritis fibroblast-like synoviocytes. Inflammation. 2014 Aug;37(4):1050-8. [4]. Yan S, et al. Bufalin enhances TRAIL-induced apoptosis by redistributing death receptors in lipid rafts in breast cancer cells. Anticancer Drugs. 2014 Jul;25(6):683-9. [5]. Wen L, et al. Anti-inflammatory and antinociceptive activities of bufalin in rodents. Mediators Inflamm. 2014;2014:171839. Chemical & Physical Properties 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 |
| Use of | Properties Articles27 Name bufalin Synonym More Synonyms Bufalin Biological Activity Related Catalog Signaling Pathways >> Others >> Others Research Areas >> Cancer Natural Products >> Steroids References [1]. Jiang L, et al. Bufalin induces cell cycle arrest and apoptosis in gallbladder carcinoma cells. Tumour Biol. 2014 Nov;35(11):10931-41. [2]. Wu SH, et al. Bufalin induces cell death in human lung cancer cells through disruption of DNA damage response pathways. Am J Chin Med. 2014;42(3):729-42. [3]. Rong X, et al. Bufalin, a bioactive component of the chinese medicine chansu, inhibits inflammation and invasion of human rheumatoid arthritis fibroblast-like synoviocytes. Inflammation. 2014 Aug;37(4):1050-8. [4]. Yan S, et al. Bufalin enhances TRAIL-induced apoptosis by redistributing death receptors in lipid rafts in breast cancer cells. Anticancer Drugs. 2014 Jul;25(6):683-9. [5]. Wen L, et al. Anti-inflammatory and antinociceptive activities of bufalin in rodents. Mediators Inflamm. 2014;2014:171839. Chemical & Physical Properties Molecular Formula C24H34O4 Exact Mass 386.245697 PSA 70.67000 Index of Refraction 1.594 InChIKey QEEBRPGZBVVINN-ONGIWDLKSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Danger Regulations: 3462 International Maritime Transport Danger Regulations: 3462 International Air Transport Danger Regulations: 3462 14.2 United Nations shipping name European land transport hazard regulations: TOXINS EXTRACTED FROM LIVING SOURCES, SOLID, N.O.S. (3β-14-Dihydroxy-5β- bufa-20,22-dienolide) IMDG: TOXINS, EXTRACTED FROM LIVING SOURCES, SOLID, N.O.S. (3β-14-Dihydroxy-5β- bufa-20,22-dienolide) International air transport hazard regulations: Toxins, extracted from living sources, solid, n.o.s. (3β-14-Dihydroxy-5β-bufa-20,22- dienolide) 14.3 Transport hazard categories European Land Transport Danger Regulations: 6.1 International Maritime Transport Danger Regulations: 6.1 International Air Transport Danger Regulations: 6.1 14.4 Package group European Dangerous Regulations for land transport: II International Dangerous Regulations for sea transport: II International Dangerous Regulations for air transport: II 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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