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Vincristine . sulfate

CHF 55.00
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AG-CN2-0446-M0055 mgCHF 55.00
AG-CN2-0446-M02525 mgCHF 180.00
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Product Details
Synonyms VCR; 22-Oxovincaleukoblastine; NSC 67574; Oncovin; Lilly 37231; Leucristine; Leurocristine; LS-228
Product Type Chemical
Properties
Formula

C46H56N4O10 . H2SO4

MW 825.0 . 98.1
Merck Index 14: 9986
CAS 2068-78-2
RTECS OH6340000
Source/Host Chemicals Synthetic. Originally isolated from Vinca rosea.
Purity Chemicals ≥98% (HPLC)
Appearance White to light-yellow powder.
Solubility Soluble in water, DMSO or methanol.
Identity Determined by 1H-NMR.
InChi Key AQTQHPDCURKLKT-JKDPCDLQSA-N
Smiles OS(O)(=O)=O.[H]C(=O)N1C2=C(C=C(C(OC)=C2)[C@]2(C[C@@H]3C[N@@](C[C@](O)(CC)C3)CCC3=C2NC2=C3C=CC=C2)C(=O)OC)[C@@]23CCN4CC=C[C@@](CC)([C@@H](OC(C)=O)[C@](O)(C(=O)OC)[C@]12[H])[C@@]34[H]
Shipping and Handling
Shipping AMBIENT
Short Term Storage +20°C
Long Term Storage +4°C
Handling Advice Protect from light and moisture.
Use/Stability Stable for at least 2 years after receipt when stored at +4°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Immunosuppressant.
  • Anticancer compound. Chemotherapeutic agent.
  • Depolymerizes microtubules and irreversibly blocks binding of tubulin to microtubule proteins.
  • Apoptosis inducer and cell cycle inhibitor in G2/M phase.
  • Autophagy inhibitor. Inhibits microtubule-mediated fusion of autophagosome with lysosme.
  • Inducer of IL-1β production.
  • Activates alone and synergistically together with doxorubicin the NLRP3-inflammasome mediated processing of IL-1β.
  • Monoamine oxidase (MAO) inhibitor.
Product References
  1. Suppression of immune response by Vincristine and Vinblastine: A.C. Aisenberg; Nature 200, 484 (1963)
  2. Vinblastine and vincristine are inhibitors of monoamine oxidase B: J.K. Son, et al.; J. Med. Chem. 33, 1845 (1990)
  3. Cell death induced by vincristine in the intestinal crypts of mice and in a human Burkitt's lymphoma cell line: B.V. Harmon, et al.; Cell Prolif. 25, 523 (1992)
  4. Interaction of vinca alkaloids with tubulin: a comparison of vinblastine, vincristine, and vinorelbine: S. Lobert, et al.; Biochemistry 35, 6806 (1996)
  5. Antimitotic natural products and their interactions with tubulin: E. Hamel; Med. Res. Rev. 16, 207 (1996)
  6. Raf-1/bcl-2 phosphorylation: a step from microtubule damage to cell death: M.V. Blagosklonny, et al.; Cancer Res. 57, 130 (1997)
  7. Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle: A. Jordan, et al.; Med. Res. Rev. 18, 259 (1998) (Review)
  8. The effect of antimicrotubule agents on signal transduction pathways of apoptosis: a review: L.G. Wang; Cancer Chemother. Pharmacol. 44, 355 (1999) (Review)
  9. Vincristine-induced apoptosis in vivo in peripheral blood mononuclear cells of children with acute lymphoblastic leukaemia (ALL): E. Groninger, et al.; Br. J. Haematol. 111, 875 (2000)
  10. Autophagy-mediated HMGB1 release antagonizes apoptosis of gastric cancer cells induced by vincristine via transcriptional regulation of Mcl-1: Z. Zhan, et al.; Autophagy 8, 109 (2012)
  11. Autophagy and microtubules - new story, old players: R. Mackeh, et al.; J. Cell Sci. 126, 1071 (2013) (Review)
  12. Production of IL-1β by bone marrow-derived macrophages in response to chemotherapeutic drugs: synergistic effects of doxorubicin and vincristine: J. Wong, et al.; Cancer Biol. Ther. 15, 1395 (2014)
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