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Cinobufotalin

$538

  • Brand : BIOFRON

  • Catalogue Number : BD-P0738

  • Specification : 99.0%(HPLC&TLC)

  • CAS number : 1108-68-5

  • PUBCHEM ID : 259776

  • Volume : 25mg

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Catalogue Number

BD-P0738

Analysis Method

HPLC,NMR,MS

Specification

99.0%(HPLC&TLC)

Storage

2-8°C

Molecular Weight

Appearance

White crystalline powder

Botanical Source

Bufo bufo gargarizans Cantor/Ch'an Su, the dried venom of Chinese toads

Structure Type

Cardenolides and its Sapogenins

Category

Standards;Natural Pytochemical;API

SMILES

CC(=O)OC1C(C2(CCC3C(C24C1O4)CCC5(C3(CCC(C5)O)C)O)C)C6=COC(=O)C=C6

Synonyms

14,15b-Epoxy-3b,5a,16b-trihydroxy-5b,20(22)-bufadienolide 16-acetate/(3b,5b,15b,16b)-16-(Acetyloxy)-14,15-epoxy-3,5-dihydroxybufa-20,22-dienolide/Bufa-20,22-dienolide, 16- (acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β,16β)-/5beta-Hydroxycinobufagin/5β-Bufa-20,22-dienolide, 14,15β-epoxy-3β,5,16β-trihydroxy-, 16-acetate (8CI)/Bufa-20,22-dienolide, 16-(acetyloxy)-14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β,16β)-/cinobufotalin venom toad/Cinobufotlin/14,15-Epoxy-14H-cyclopenta[a]phenanthrene,bufa-20,22-dienolide deriv./Cinobufotalin/CINOBUFOTALIN(RG)/cinobufatolin/(3β,5β,15β,16β)-16-Acetoxy-3,5-dihydroxy-14,15-epoxybufa-20,22-dienolide/14,15b-Epoxy-3b,5,16b-trihydroxy-5b-bufa-20,22-dienolide 16-Acetate

IUPAC Name

[(1R,2S,4R,5R,6R,7R,10S,11R,14S,16S)-14,16-dihydroxy-7,11-dimethyl-6-(6-oxopyran-3-yl)-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-5-yl] acetate

Applications

Cinobufotalin is one of the bufadienolides prepared from toad venom; has anticancer activity.IC50 value:Target:in vitro: Cinobufotalin(CB) caused significant DNA fragmentation, decrease of MMP, and an increase in the intracellular Ca(2+) ion and ROS production. In addition, CB induced upregulation of Fas protein, proteolytic activation of cytochrome c, caspase-2, -3, -8 and -9 together with the activation of Bid and Bax [1]. cinobufotalin displayed considerable cytotoxicity against lung cancer cells (A549, H460 and HTB-58 lines) without inducing significant cell apoptosis. cinobufotalin mainly induces Cyp-D-dependent non-apoptotic death in cultured lung cancer cells [2]. cinobufotalin (at nmol/L) significantly inhibited HCC cell growth and survival while inducing considerable cell apoptosis. Further, cinobufotalin inhibited sphingosine kinase 1 (SphK1) activity and induced pro-apoptotic ceramide production. cinobufotalin inactivated Akt-S6K1 signaling in HepG2 cells, which was again inhibited by ceramide synthase-1 shRNA-depletion [3].in vivo: Using a mice xenograft model, we found that cinobufotalin inhibited A549 lung cancer cell growth in vivo [2].

Density

1.3±0.1 g/cm3

Solubility

Methanol; Acetontrile; Chloroform; DMSO

Flash Point

210.7±25.0 °C

Boiling Point

627.3±55.0 °C at 760 mmHg

Melting Point

259 - 262ºC

InChl

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

InChl Key

KBKUJJFDSHBPPA-ZNCGZLKOSA-N

WGK Germany

RID/ADR

HS Code Reference

3002900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:1108-68-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27699589

Abstract

Preeclampsia (preE) is a hypertensive disorder of pregnancy. Cardiotonic steroids (CTS) are endogenous inhibitors of Na+/K+ ATPase, and at least one CTS, marinobufagenin (MBG), is elevated in a rat model of preE prior to the development of the syndrome. MBG and ouabain impair cytotrophoblast (CTB) cell function, which is critical for placental development. We evaluated the effect of a CTS, cinobufotalin (CINO), on CTB cell function in vitro. CINO at ≥1 nM inhibited CTB cell proliferation, migration, and invasion (p < 0.05), but had no effect on cell viability. There was a higher (p < 0.05) percentage of G0/G1 phase cells in groups treated with CINO at ≥1 nM. CINO caused an increase in stress signaling p38 MAPK and a positive annexin-V staining in CTB cells, indicating the activation of apoptotic signaling. However, the CINO-induced apoptotic signaling was prevented by p38 inhibition. These data demonstrate that CINO impairs CTB cell function via cell cycle arrest and apoptotic signaling.

KEYWORDS

Apoptosis; Cell signaling; Cinobufotalin; Cytotrophoblast; Preeclampsia.

Title

Cinobufotalin Impedes Sw.71 Cytotrophoblast Cell Line Function via Cell Cycle Arrest and Apoptotic Signaling

Author

Syeda H Afroze 1 , Jenna Sloan 2 , Grace-Ann C Osuji 3 , Nathan Drever 2 , Kimberly Pilkinton 2 , David C Zawieja 1 , Thomas J Kuehl 2 4 , M Nasir Uddin 5 6 7

Publish date

2016 Nov

PMID

31464940

Abstract

Background and objective: Cinobufotalin injection (CFI), a kind of Chinese medicine, has been considered as a promising complementary therapy option for advanced non-small cell lung cancer (NSCLC), but their efficacy and safety remain controversial. This study aimed to systematically evaluate the efficacy and safety of CFI and chemotherapy-combined therapy for advanced NSCLC.
Methods: Clinical trials were searched from Web of Science, Cochrane Library, PubMed, Embase, China National Knowledge Infrastructure (CNKI), Chinese Biological Medicine Database (CBM), Chinese Medical Citation Index (CMCI), Wanfang database and Chinese Scientific Journal Database (VIP). Main measurements, including therapeutic efficacy, quality of life (QoL) and adverse events, were extracted from the retrieved publications and were systematically evaluated.
Results: The 29 trials including 2300 advanced NSCLC patients were involved in this study. Compared with chemotherapy alone, its combination with CFI significantly prolonged the patients’ 1-, 2- and 3-year overall survival rate (OS) (1-year OS, OR = 1.94, 95% CI = 1.42-2.65, P < .0001; 2-year OS, OR = 2.31, 95% CI = 1.55-3.45, P < .0001; 3-year OS, OR = 4.69, 95% CI = 1.78-12.39, P = .002) and improved patients' overall response (ORR, OR = 1.84, CI = 1.54-2.18, P < .00001), disease control rate (DCR, OR = 2.09, 95% CI = 1.68-2.60, P < .00001) and QoL (quality of life improved rate, QIR, OR = 2.64, 95% CI = 1.98-3.52, P < .00001; karnofsky performance score, KPS, OR = 10.97, 95% CI = 5.48-16.47, P < .0001). Most adverse events caused by chemotherapy were obviously alleviated (P < .05) when CFI was also applied to patients. Conclusion: The combination of CFI and chemotherapy is safe, and is more effective in treating NSCLC than chemotherapy alone. Therefore, CFI mediated therapy could be recommended as an adjuvant treatment method for NSCLC.

Title

Cinobufotalin Injection Combined With Chemotherapy for the Treatment of Advanced NSCLC in China: A PRISMA-compliant Meta-Analysis of 29 Randomized Controlled Trials

Author

Fan Zhang 1 , Yantong Yin 2 , Tiantian Xu 1

Publish date

2019 Aug

PMID

31118669

Abstract

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), Chinese Biological Medicine Database (CBM), Wanfang database and Chinese Scientific Journal Database (VIP) before September 2018. The primary reported outcomes including therapeutic efficacy, quality of life (QoL), and adverse events were systematically evaluated. Results: Data from 27 trials including 1,939 advanced GC patients were included. The results indicated that, compared with chemotherapy alone, the combination of chemotherapy and cinobufotalin significantly improved patients’ overall response rate (odds ratio [OR] =1.88, 95% confidence interval [CI] =1.54-2.31, P<0.00001) and disease control rate (OR =2.05, 95% CI =1.63-2.58, P<0.00001). The QoL of patients also evidently improved after chemotherapy and cinobufotalin combined treatment, as indicated by increased QoL improved rate (OR =2.39, 95% CI =1.81-3.15, P<0.00001), Karnofsky Performance Score (OR =7.00, 95% CI =2.25-11.75, P=0.004) and pain relief rate (OR =7.00, 95% CI =2.25-11.75, P=0.004). Adverse events including nausea and vomiting, diarrhea, leukopenia, hand-foot syndrome, anemia, gastrointestinal side effects and peripheral neurotoxicity caused by chemotherapy were evidently alleviated (P<0.05) when cinobufotalin was administered to GC patients. Conclusion: Evidence from the meta-analysis suggested that the combination of chemotherapy and cinobufotalin is more effective in treating GC than chemotherapy alone. It alleviates the adverse effects associated with chemotherapy and improves the QoL of GC patients.

KEYWORDS

chemotherapy; cinobufotalin; gastric cancer; meta-analysis; traditional Chinese medicine.

Title

Cinobufotalin as an Effective Adjuvant Therapy for Advanced Gastric Cancer: A Meta-Analysis of Randomized Controlled Trials

Author

Huiling Sun 1 , Wenxiao Wang 2 , Minghua Bai 3 , Dongling Liu 4

Publish date

2019 Apr 26