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Hellebrin

AG-CN2-0475-M001 1 mg INQ
AG-CN2-0475-M005 5 mg INQ
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Additional Information

Product Data
Synonyms 3β-(O4-β-D-Glucopyranosyl-α-L-rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5β,14-β-bufa-20,22-dienolide; NSC93134
Properties
Formula C36H52O15
MW 724.8
CAS 13289-18-4
Source/Host Isolated from Helleborus purpurascens.
Purity ≥99% (HPLC and UV Absorbance)
Appearance White to off-white solid.
Solubility Soluble in water (~4mg/ml).
InChi Key DCSLTSSPIJWEJN-YRFFWODSSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry. Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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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.

Product References

  1. Ueber Hellebrin, ein krystallisiertes Glykosid aus Radix Hellebori nigri: W. Karrer; Helv. Chim. Acta 26, 1353 (1943)
  2. The structure of hellebrin: P. Muhr, et al.; Liebigs Ann. Org. Bioorg. Chem. 2, 443 (1995)
  3. In search of ideal inotropic steroids: recent progress: K.R. Repke, et al.; Prog. Drug Res. 47, 9 (1996)
  4. Exquisitely small amounts of nonglucocorticoid natural steroids suppress the human allogeneic T-cell response: P. Terness, et al.; Transplant Proc. 33, 547 (2001)
  5. The T-cell suppressive effect of bufadienolides: structural requirements for their immunoregulatory activity: P. Terness, et al.; Int. Immunopharmacol. 1, 119 (2001)
  6. 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)
  7. Anti-cancer natural product library from traditional chinese medicine: V.B. Konkimalla & T. Efferth; Comb. Chem. High Throughput Screen. 11, 7 (2008)
  8. 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)
  9. 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)
  10. 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)
  11. Natural compounds with important medical potential found in Helleborus sp.: M.C. Maior & C. Dobrota; Cent. Eur. J. Biol. 8, 272 (2013) (Review)
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