Vincristine sulfate

Vincristine sulfate is the sulfate salt of a natural alkaloid isolated from the periwinkle plant of the oleander family with antimitotic and antineoplastic activities. Vincristine binds irreversibly to microtubules and spindle proteins in S phase of the cell cycle and interferes with the formation of the mitotic spindle, thereby arresting tumor cells in metaphase. This agent also depolymerizes microtubules and may also interfere with amino acid, cyclic AMP, and glutathione metabolism; calmodulin-dependent Ca++ -transport ATPase activity; cellular respiration; and nucleic acid and lipid biosynthesis.

Product information

CAS Number: 2068-78-2

Molecular Weight: 923.04

Formula: C46H58N4O14S

Synonym:

leurocristine sulfate

Vincasar PFS

Oncovin

VCR

Related CAS Number:

57-22-7 (Vincristine free base)

Chemical Name: (3aR, 3a1R, 4R, 5S, 5aR, 10bR)-methyl 4-acetoxy-3a-ethyl-9-((3S, 5S, 7S, 9S)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-2, 4, 5, 6, 7, 8, 9, 10-octahydro-1H-3, 7-methano[1]azacycloundecino[5, 4-b]indol-9-yl)-6-formyl-5-hydroxy-8-methoxy-3a, 3a1, 4, 5, 5a, 6, 11, 12-octahydro-1H-indolizino[8, 1-cd]carbazole-5-carboxylate sulfate.

Smiles: CC(=O)O[C@@H]1[C@]2(CC)C=CCN3CC[C@]4([C@@H](N(C=O)C5=CC(OC)=C(C=C45)[C@]4(C[C@H]5C[C@](O)(C[N@](C5)CCC5=C4NC4=CC=CC=C54)CC)C(=O)OC)[C@@]1(O)C(=O)OC)[C@H]23.OS(O)(=O)=O

InChiKey: AQTQHPDCURKLKT-JKDPCDLQSA-N

InChi: InChI=1S/C46H56N4O10.H2O4S/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)25-42)29-12-9-10-13-33(29)47-36)32-20-31-34(21-35(32)57-4)50(26-51)38-44(31)16-19-49-17-11-15-43(8-2,37(44)49)39(60-27(3)52)46(38,56)41(54)59-6;1-5(2,3)4/h9-13,15,20-21,26,28,37-39,47,55-56H,7-8,14,16-19,22-25H2,1-6H3;(H2,1,2,3,4)/t28-,37+,38-,39-,42+,43-,44-,45+,46+;/m1./s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO: 100 mg/mL(108.33 mM). Water: 60 mg/mL(65.0 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Vincristine inhibits net addition of tubulin dimers at assembly ends of steady-state microtubules with Ki of 85 nM. At low concentrations, Vincristine stabilizes the spindle apparatus resulting in failure of the chromosomes to segregate leading to metaphase arrest and inhibition of mitosis. At higher concentrations, Vincristine may disrupt and induce total depolymerization of microtubules. Vincristine induces apoptosis in tumor cells and inhibits SH-SY5Y cell proliferation with IC50 of 0.1 μM. Vincristine induces mitotic arrest and promots the expression of caspase-3 and -9 and cyclin B, while decreasing the expression of cyclin D. Vincristine induced neurotoxicity is caused by interference with microtubule function, which results in blockage of axonal transport and thus in axonal degeneration.

In Vivo:

Vincristine (3 mg/kg) administrated by a single i.p. injection to mice bearing bilateral subcutaneous xenografts Rh12 or Rh18, induces mean growth delay of >120 and >52 day, and repopulating fractions of 0.06% and 5%, respectively. Vincristine acts on subcutaneous colon 38 tumors in mice by host cell-mediated vascular effects as well as by direct tubulin-mediated cytotoxicity. Vincristine (5 mg/kg) reduces tumor blood flow of tumors by nearly 75% .

References:

1. Tu Y, et al. Int J Mol Med, 2013, 31(1), 113-119.
2. Gidding CE. Crit Rev Oncol Hematol, 1999, 29(3), 267-287.
3. Jordan MA, et al. Cancer Res, 1985, 45(6), 2741-2747.

Products are for research use only. Not for human use.