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ProductsBack/Hellebrin [13289-18-4]
Chemical Structure
Chemical Structure
Chemical Structure

Hellebrin [13289-18-4]

Research Use Only
AG-CN2-0475
AdipoGen Life Sciences
CAS Number13289-18-4
DownloadMSDS
Product group Chemicals
Estimated Purity>99%
Molecular Weight724.8
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Hellebrin
  • Delivery Days Customer
    10
  • ADR Class
    6.1
  • CAS Number
    13289-18-4
  • Certification
    Research Use Only
  • Estimated Purity
    >99%
  • Hazard Information
    Danger,Excepted quantity
  • Molecular Formula
    C36H52O15
  • Molecular Weight
    724.8
  • Scientific 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. - 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.
  • 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
  • Storage Instruction
    -20°C,2°C to 8°C
  • UN Number
    UN 2811
  • UNSPSC
    12352200

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)