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C1147

Sigma-Aldrich

Cinobufotalin

Sinônimo(s):

14,15β-Epoxy-3β,5α,16β-trihydroxy-5β,20(22)-bufadienolide 16-acetate, 5β,20(22)-Bufadienolide-14,15β-epoxy-3β,5α,16β-triol 16-acetate

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About This Item

Fórmula empírica (Notação de Hill):
C26H34O7
Número CAS:
1108-68-5
Peso molecular:
458.54
Número MDL:
MFCD28396383
Código UNSPSC:
12352200
ID de substância PubChem:
24892362
NACRES:
NA.77

forma

solid

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

C[C@@]12[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]35O[C@@H]5[C@H](OC(C)=O)[C@@H]4C6=COC(C=C6)=O)(O)C[C@@H](O)CC1

InChI

1S/C26H34O7/c1-14(27)32-21-20(15-4-5-19(29)31-13-15)24(3)10-7-17-18(26(24)22(21)33-26)8-11-25(30)12-16(28)6-9-23(17,25)2/h4-5,13,16-18,20-22,28,30H,6-12H2,1-3H3/t16-,17-,18+,20-,21+,22+,23+,24+,25-,26+/m0/s1

chave InChI

KBKUJJFDSHBPPA-ZNCGZLKOSA-N

Descrição geral

Cinobufotalin is a cardiotonic steroid or bufotalin. It is mainly obtained from the skin secretion of the giant toad.

Aplicação

Cinobufotalin has been used:
  • as a standard to bound them with the Fab fragment of an anti-digoxin antibody (Digibind) to rapidly detect its presence in blood by the fluorescence polarization immunoassay for digitoxin
  • to treat human cancer cell lines/MCF-7 cells to examine the steroid receptor coactivator-3 (SRC-3) protein concentrations and evaluate its efficacy as SRC small-molecule inhibitors (SMIs)
  • as a standard to calibrate the high-performance liquid chromatography (HPLC) and calculate the total quantity of bufadienolides present in the nuchal gland fluid of Rhabdophis tigrinus

Ações bioquímicas/fisiológicas

Cinobufotalin, a diuretic, and a hemostatic agent can stimulate cytotoxic effect in cultured lung cancer cells. It can suppress the development of A549 cells in vivo. Cinobufotalin possesses antitumor activity and enhanced chemotherapeutic effect. It can inhibit the vascular endothelial growth factor and epidermal growth factor receptor expression to prevent the development and metastasis of the tumor. It may be beneficial to advance gastric cancer (GC) patients. This safe auxiliary antitumor agent can reduce the adverse events related to chemotherapy.

Pictogramas

Skull and crossbones
GHS06

Palavra indicadora

Danger

Frases de perigo

H300 + H310 + H330

Classificações de perigo

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Código de classe de armazenamento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de risco de água (WGK)

WGK 3

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Ting-Ting Wang et al.
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine, 29(10), 915-917 (2010-01-16)
To investigate the effect of cinobufagin on the proliferation of lens epithelial cells (LECs) and the bcl-2 and bax mRNA expressions of rabbits. Cultured LECs were treated for 72 h with cinobufagin of different concentrations, the end titer was 0.1
D A Hutchinson et al.
Journal of zoology (London, England : 1987), 289(4), 270-278 (2013-07-16)
Species that sequester toxins from prey for their own defense against predators may exhibit population-level variation in their chemical arsenal that reflects the availability of chemically defended prey in their habitat.
Huiling Sun et al.
OncoTargets and therapy, 12, 3139-3160 (2019-05-24)
Purpose: This study aimed to investigate the efficacy and safety of combining cinobufotalin and chemotherapy for advanced gastric cancer (GC). Patients and methods: Literature retrieval was performed in Cochrane Library, Web of Science, PubMed, Embase, China National Knowledge Infrastructure (CNKI)
Xin Liu et al.
Zhongguo Zhong xi yi jie he za zhi Zhongguo Zhongxiyi jiehe zazhi = Chinese journal of integrated traditional and Western medicine, 28(2), 105-107 (2008-04-05)
To investigate the effect of traditional Chinese medicine (TCM) on quality of life (QOF) and survival period in patients with progressive gastric cancer, and thus exploring its clinical efficacy. TCM therapy applied in the 34 patients assigned in the TCM
A A Brownlee et al.
Clinical science (London, England : 1979), 78(2), 169-174 (1990-02-01)
1. We have reported that the bufadienolide, bufalin (purified from toad skin), was more potent than ouabain in inhibiting the sodium/potassium-dependent adenosine triphosphatase from canine kidney (Sigma) [Brownlee, A.A., Lee, G. & Mills, I.H.J. Physiol. (London) 1987; 390, 94P]. 2.
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