CAS 471-95-4|Bufotaline
Introduction：Basic information about CAS 471-95-4|Bufotaline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Bufotaline | ||
|---|---|---|---|
| CAS Number | 471-95-4 | Molecular Weight | 444.560 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 591.7±50.0 °C at 760 mmHg |
| Molecular Formula | C26H36O6 | Melting Point | 223°C (rough estimate) |
| MSDS | / | Flash Point | 195.8±23.6 °C |
Names
| Name | Bufotaline |
|---|---|
| Synonym | More Synonyms |
Bufotaline BiologicalActivity
| Description | Bufotalin is a cardiotoxic bufanolide steroid, cardiac glycoside analogue, secreted by a number of toad species; a novel anti-osteoblastoma agent.IC50 value:Target:in vitro: bufotalin induced osteoblastoma cell death and apoptosis in dose- and time-dependent manners. Further, bufotalin induced endoplasmic reticulum (ER) stress activation in osteoblastoma cells, the latter was detected by the induction of C/EBP homologous protein (CHOP), phosphorylation of inositol-requiring enzyme 1 (IRE1) and PKR-like endoplasmic reticulum kinase (PERK), as well as caspase-12 activation [1]. Bufotalin was the most potent active compound among these four bufadienolides, and it exerted stronger inhibitory effect on the viability of doxorubicin-induced multidrug resistant liver cancer cells (R-HepG2) than that of their parent cells HepG2. bufotalin treatment induced cell cycle arrest at G(2)/M phase through down-regulation of Aurora A, CDC25, CDK1, cyclin A and cyclin B1, as well as up-regulation of p53 and p21. Bufotalin treatment also induced apoptosis which was accompanied by decrease in mitochondrial membrane potential, increases in intracellular calcium level and reactive oxygen species production, activations of caspase-9 and -3, cleavage of poly ADP-ribose polymerase (PARP) as well as changes in the expressions of bcl-2 and bax [2]. Bufotalin promoted death receptor-mediated cell death, especially TRAIL-induced apoptosis, through activation of caspase-3 and PARP-1. Cotreatment of bufotalin with TRAIL resulted in the downregulation of anti-apoptotic proteins, including Bcl-XL, Mcl-1, survivin and XIAP, and the up-regulation of MAPKs and TRAIL receptor DR5. In addition, phosphorylation of STAT1 was strongly inhibited by bufotalin [3]. externalization of phosphatidylserine, accumulation of sub-G(1) cells, fragmentation of DNA, and formation of apoptotic bodies were observed in bufotalin-treated Hep 3B cells [4]. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>OthersNatural Products >>SteroidsResearch Areas >>Cancer |
| References | [1]. Zhu YR, et al. Bufotalin-induced apoptosis in osteoblastoma cells is associated with endoplasmic reticulum stress activation. Biochem Biophys Res Commun. 2014 Aug 15;451(1):112-8. [2]. Zhang DM, et al. Bufotalin from Venenum Bufonis inhibits growth of multidrug resistant HepG2 cells through G2/M cell cycle arrest and apoptosis. Eur J Pharmacol. 2012 Oct 5;692(1-3):19-28. [3]. Waiwut P, et al. Bufotalin sensitizes death receptor-induced apoptosis via Bid- and STAT1-dependent pathways. Int J Oncol. 2012 Jan;40(1):203-8. [4]. Su CL, et al. Involvement of caspases and apoptosis-inducing factor in bufotalin-induced apoptosis of Hep 3B cells. J Agric Food Chem. 2009 Jan 14;57(1):55-61. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 591.7±50.0 °C at 760 mmHg |
| Melting Point | 223°C (rough estimate) |
| Molecular Formula | C26H36O6 |
| Molecular Weight | 444.560 |
| Flash Point | 195.8±23.6 °C |
| Exact Mass | 444.251190 |
| PSA | 96.97000 |
| LogP | 2.54 |
| Vapour Pressure | 0.0±3.8 mmHg at 25°C |
| Index of Refraction | 1.587 |
| InChIKey | VOZHMAYHYHEWBW-NVOOAVKYSA-N |
| SMILES | CC(=O)OC1CC2(O)C3CCC4CC(O)CCC4(C)C3CCC2(C)C1c1ccc(=O)oc1 |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 400 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 4,331,1971
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4130 ug/kg
- TOXIC EFFECTS :
- Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Behavioral - antipsychotic
- REFERENCE :
- CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 24,1714,1976
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1131 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- PHUZBI Pharmazie in Unserer Zeit. (VCH Pub., Inc., 303 N.W. 12th Ave., Deerfield Beach, FL 33441) V.1- 1972- Volume(issue)/page/year: 13,129,1984
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 980 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 152,571,1958
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 360 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 152,571,1958
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 136 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 74,223,1942
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 130 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- PHUZBI Pharmazie in Unserer Zeit. (VCH Pub., Inc., 303 N.W. 12th Ave., Deerfield Beach, FL 33441) V.1- 1972- Volume(issue)/page/year: 13,129,1984
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Amphibian - frog
- DOSE/DURATION :
- 1200 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. (Leipzig, Ger. Dem. Rep.) V.1-109, 1873-1925. For publisher information, see NSAPCC. Volume(issue)/page/year: 86,138,1920
Safety Information
| RIDADR | UN 3172 |
|---|---|
| Packaging Group | II |
| Hazard Class | 6.1(a) |
| HS Code | 29329990 |
Synonyms
| Bufotaline |
| Bufotalin std. |
| 16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide |
| BUFOTALIN(SH) |
| BUFOTALIN SULFATE |
| Bufa-20,22-dienolide, 16-(acetyloxy)-3,14-dihydroxy-, (3β,5β,16β)- |
| (3b,5b,16b)-16-(Acetyloxy)-3,14-dihydroxybufa-20,22-dienolide |
| (3S,5R,8R,9S,10S,13R,14S,16S,17R)-3,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-16-yl acetate |
| 5β-Bufa-20,22-dienolide, 3β,14,16β-trihydroxy-, 16-acetate (8CI) |
| Bufotalin |
| 3b,14,16b-Trihydroxy-5b-bufa-20,22-dienolide 16-Acetate |
| (3β,5β,16β)-16-Acetoxy-3,14-dihydroxybufa-20,22-dienolide |
