Hellebrin
| Code | Size | Price |
|---|
| AG-CN2-0475-M001 | 1 mg | £55.00 |
Quantity:
| AG-CN2-0475-M005 | 5 mg | £180.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
Short Tem: +4°C, Long Term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
3beta-(O4-beta-D-Glucopyranosyl-alpha-L-rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5beta,14-beta-bufa-20,22-dienolide; NSC93134
Appearance:
White to off-white solid.
CAS:
13289-18-4
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Keep cool and dry.Protect from light and moisture.Aqueous solutions should not be stored for longer than one day.
Hazards:
H300, H310, H330
InChi:
InChI=1S/C36H52O15/c1-17-30(51-32-28(43)26(41)25(40)23(14-37)50-32)27(42)29(44)31(48-17)49-19-5-10-34(16-38)21-6-9-33(2)20(18-3-4-24(39)47-15-18)8-12-36(33,46)22(21)7-11-35(34,45)13-19/h3-4,15-17,19-23,25-32,37,40-46H,5-14H2,1-2H3/t17-,19-,20+,21-,22+,23+,25+,26-,27-,28+,29+,30-,31-,32-,33+,34-,35-,36-/m0/s1
InChiKey:
DCSLTSSPIJWEJN-YRFFWODSSA-N
Long Description:
Chemical. CAS: 13289-18-4. Formula: C36H52O15. MW: 724.8. Isolated from Helleborus purpurascens. Highly potent Na+/K+-ATPase inhibitor, blocking the active efflux of Na+ and reuptake of K+. Water soluble cardiotonic glycoside from the class of bufadienolides (with 2-pyrone ring). Inhibits cancer cell growth in vitro. Shown to induce caspase-dependent apoptosis, reducing MDR resistance and the rate of mitochondrial oxidative phosphorylation in cancer cells. Inotropic by increasing the intracellular Ca2+ concentration. Immunosuppressive and anti-inflammatory agent that inhibits allogeneic T cell activation with much higher potency than cortisol or cyclosporin A.
MDL:
MFCD03265649
Molecular Formula:
C36H52O15
Molecular Weight:
724.8
Package Type:
Vial
PG:
I
Precautions:
P260, P270, P280, P301, P310, P302, P352, P304, P340, P405
Product Description:
Highly potent Na+/K+-ATPase inhibitor, blocking the active efflux of Na+ and reuptake of K+. Water soluble cardiotonic glycoside from the class of bufadienolides (with 2-pyrone ring). Inhibits cancer cell growth in vitro. Shown to induce caspase-dependent apoptosis, reducing MDR resistance and the rate of mitochondrial oxidative phosphorylation in cancer cells. Inotropic by increasing the intracellular Ca2+ concentration. Immunosuppressive and anti-inflammatory agent that inhibits allogeneic T cell activation with much higher potency than cortisol or cyclosporin A. Anti-seizure activity in pentylenetetrazole (PTZ)-induced epileptical seizures.
Purity:
>99% (HPLC and UV Absorbance)
Signal word:
Danger
SMILES:
[H]C(=O)[C@]12CC[C@@H](C[C@@]1(O)CCC1C2CC[C@]2(C)[C@H](CC[C@]12O)C1=COC(=O)C=C1)O[C@@H]1OC(C)[C@H](O[C@@H]2OC(CO)[C@@H](O)[C@@H](O)C2O)[C@H](O)C1O
Solubility Chemicals:
Soluble in water (~4mg/ml).
Source / Host:
Isolated from Helleborus purpurascens.
Transportation:
Excepted Quantity
UN Nummer:
UN 2811
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352211
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Ueber Hellebrin, ein krystallisiertes Glykosid aus Radix Hellebori nigri: W. Karrer; Helv. Chim. Acta 26, 1353 (1943) | The structure of hellebrin: P. Muhr, et al.; Liebigs Ann. Org. Bioorg. Chem. 2, 443 (1995) | In search of ideal inotropic steroids: recent progress: K.R. Repke, et al.; Prog. Drug Res. 47, 9 (1996) | Exquisitely small amounts of nonglucocorticoid natural steroids suppress the human allogeneic T-cell response: P. Terness, et al.; Transplant Proc. 33, 547 (2001) | The T-cell suppressive effect of bufadienolides: structural requirements for their immunoregulatory activity: P. Terness, et al.; Int. Immunopharmacol. 1, 119 (2001) | Apoptosis-mediated selective killing of malignant cells by cardiac steroids: maintenance of cytotoxicity and loss of cardiac activity of chemically modified derivatives: D. Daniel, et al.; Int. Immunopharmacol. 3, 1791 (2003) | Anti-cancer natural product library from traditional chinese medicine: V.B. Konkimalla & T. Efferth; Comb. Chem. High Throughput Screen. 11, 7 (2008) | FTIR spectral signature of the effect of cardiotonic steroids with antitumoral properties on a prostate cancer cell line: R. Gasper, et al.; Biochim. Biophys. Acta 1802, 1087 (2010) | Hellebrin and its aglycone form hellebrigenin display similar in vitro growth inhibitory effects in cancer cells and binding profiles to the alpha subunits of the Na+/K+-ATPase: L. Moreno Y. Banuls, et al.; Mol. Cancer 12, 33 (2013) | Structure-activity relationship analysis of bufadienolide-induced in vitro growth inhibitory effects on mouse and human cancer cells: L. Moreno Y. Banuls, et al.; J. Nat. Prod. 76, 1078 (2013) | Natural compounds with important medical potential found in Helleborus sp.: M.C. Maior & C. Dobrota; Cent. Eur. J. Biol. 8, 272 (2013) (Review) | Studies on the constituents of Helleborus purpurascens: analysis and biological activity of the aqueous and organic extracts: M. H. Franz, et al.; Amino Acids 50, 163 (2018) | Antiseizure potential of the ancient Greek medicinal plant Helleborus odorus subsp. cyclophyllus and identification of its main active principles: J. Ethnopharm. 259, 112954 (2020)