C9754

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C9754

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Colchicine

≥95% (HPLC), powder

CAS Number:64-86-8
Linear Formula:C22H25NO6
Molecular Weight:399.44
Beilstein Registry Number:2228813
EC Number:200-598-5
MDL number:MFCD00078484
PubChem Substance ID:24278348

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Description

Biochem/physiol ActionsAntimitotic agent that disrupts microtubules by binding to tubulin and preventing its polymerization. Stimulates the intrinsic GTPase activity of tubulin. Induces apoptosis in several normal and tumor cell lines and activates the JNK/SAPK signaling pathway.

Properties

assay≥95% (HPLC)
formpowder
color white to yellow with a green cast
mp150-160 °C (dec.)(lit.)
solubilityH2O: 10 mg/mL
Gene Informationhuman ... ABCB1(5243), CYP3A4(1576)
 mouse ... Abcb1a(18671), Abcb1b(18669)

Safety

Personal Protective EquipmentEyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard CodesT+
Risk Statements26/28
Safety Statements13-45
RIDADRUN1544 6.1/PG 1
WGK Germany3
RTECSGH0700000

References

referenceLuduena, R.F., et al., Tubulin structure and biochemistry. Curr. Opin. Cell Biol. 4, 53-57, (1992) Abstract
 Jordan, A., et al., Tubulin as a target for anticancer drugs: agents which interact with the mitotic spindle. Med. Res. Rev. 18, 259-296, (1998) Abstract
 Andreu, J.M., et al., Role of the colchicine ring A and its methoxy groups in the binding to tubulin and microtubule inhibition. Biochemistry 37, 8356-8368, (1998) Abstract
 Banerjee, A., Differential effects of colchicine and its B-ring modified analog MTPT on the assembly-independent GTPase activity of purified β-tubulin isoforms from bovine brain. Biochem. Biophys. Res. Commun. 231, 698, (1997) Abstract
 Suzuki, Y, Cell death, phagocytosis, and neurogenesis in mouse olfactory epithelium and vomeronasal organ after colchicine treatment. Ann. N.Y. Acad. Sci. 30, 252-254, (1998)
 DeVincenzo, R., et al., Antiproliferative activity of colchicine analogues on MDR-positive and MDR-negative human cancer cell lines. Anticancer Drug Des. 13, 19-33, (1998) Abstract
 Ceccatelli, S., et al., Apoptosis in rat hippocampal dentate gyrus after intraventricular colchicine. Neuroreport 8, 3779-3783, (1997) Abstract
 Want, T.H., et al., Microtubule-interfering agents activate c-Jun N-terminal kinase/stress-activated protein kinase through both Ras and apoptosis signal-regulating kinase pathways. J. Biol. Chem. 273, 4928-4936, (1998) Abstract
MerckMerck 13,2496
BeilsteinBeil. 14,IV,946
 Aldrich MSDS 1, 482:D / Corp MSDS 1 (1), 903:B / FT-IR 1 (2), 361:C / FT-IR 2 (2), 2980:D / FT-NMR 1 (2), 1374:C / IR-Spectra (3), 1072:F / IR-Spectra (2), 938:B / NMR-Reference 2 (2), 340:A / RegBook 1 (2), 2007:C / Sigma FT-IR 1 (2), 403:C / Structure Index 1, 320:D:5