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V8879

Sigma-Aldrich

Vincristine sulfate salt

95.0-105.0% (HPLC), powder or crystals

Synonyme(s) :

22-Oxovincaleukoblastine sulfate salt, Leurocristine sulfate salt, VCR

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About This Item

Formule empirique (notation de Hill):
C46H56N4O10 · H2SO4
Numéro CAS:
2068-78-2
Poids moléculaire :
923.04
Numéro Beilstein :
3924631
Numéro CE :
218-190-0
Numéro MDL:
MFCD00084729
Code UNSPSC :
51111767
ID de substance PubChem :
57654729
Nomenclature NACRES :
NA.85

Source biologique

Streptomyces roseosporus

Pureté

95.0-105.0% (HPLC)

Forme

powder or crystals

Conditions de stockage

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

Couleur

white to light yellow

Spectre d'activité de l'antibiotique

neoplastics

Mode d’action

protein synthesis | interferes

Température de stockage

−20°C

Chaîne SMILES 

OS(O)(=O)=O.CC[C@]1(O)CC2CN(CCc3c([nH]c4ccccc34)[C@@](C2)(C(=O)OC)c5cc6c(cc5OC)N(C=O)C7[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67C89)C(=O)OC)C1

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-;/m0./s1

Clé InChI

AQTQHPDCURKLKT-PNYVAJAMSA-N

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Application

Vincristine is an antitumor alkaloid isolated from Vinca Rosea. It is used to treat acute leukaemia, malignant lymphoma, Hodgkin′s disease, acute erythraemia, acute panmyelosis, breast cancer, Kaposi′s sarcoma and testicular cancer. Vincristine is widely used in cancer research. It is used to study multi-drug resistance. It is used to inhibit cell cycle progression at M-phase and to inhibit monoamine oxidase (MAO) .

Actions biochimiques/physiologiques

Vincristine is a plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing coiled spiral aggregate formation. It arrests cell cycle in G2/M-phase by blocking mitotic spindle formation. Vincristine triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. It inhibits VEGF production in leukemia cell lines. It is a substrate for Pgp and CYP3A4. MRP1 transports vincristine in an ATP- and GSH-dependent manner. Vincristine has some immunosuppressant effect. Vincristine may also interfere with amino acid, cyclic AMP, and glutathione metabolism, calmodulin-dependent Ca2+-transport, cellular respiration, and nucleic acid and lipid biosynthesis.

Remarque sur l'analyse

Freely soluble in water, Soluble in methanol, slightly soluble in ethanol

Autres remarques

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Pictogrammes

Skull and crossbonesHealth hazard
GHS06,GHS08

Mention d'avertissement

Danger

Mentions de danger

H300,H341,H361fd

Classification des risques

Acute Tox. 2 Oral - Muta. 2 - Repr. 2

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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J Renes et al.
British journal of pharmacology, 126(3), 681-688 (1999-04-03)
The present study was performed to investigate the ability of the multidrug resistance protein (MRPI) to transport different cationic substrates in comparison with MDR1-P-glycoprotein (MDR1). Transport studies were performed with isolated membrane vesicles from in vitro selected multidrug resistant cell
Stacey J Baker et al.
Molecular cell, 79(1), 180-190 (2020-07-04)
Rigosertib is a styryl benzyl sulfone that inhibits growth of tumor cells and acts as a RAS mimetic by binding to Ras binding domains of RAS effectors. A recent study attributed rigosertib's mechanism of action to microtubule binding. In that
Moutushy Mitra et al.
Investigative ophthalmology & visual science, 52(8), 5441-5448 (2011-05-07)
To explore the possibility of stathmin as an effective therapeutic target and to evaluate the synergistic combination of stathmin RNAi and the antimicrotubule agents paclitaxel and vincristine to retinoblastoma Y79 cells. RNAi-mediated specific inhibition of stathmin expression in Y79 cells
Trisha A Soosay Raj et al.
International journal of nanomedicine, 8, 4361-4369 (2013-11-16)
Vincristine (VCR) is one of the most extensively used cytotoxic compounds in hemato-oncology. VCR is particularly important for the treatment of acute lymphoblastic leukemia (ALL), a disease that accounts for approximately one-third of all childhood cancer diagnoses. VCR's full therapeutic
Richard Delarue et al.
The Lancet. Oncology, 14(6), 525-533 (2013-04-13)
Immunochemotherapy with rituximab and cyclophosphamide, doxorubicin, vincristine, and prednisone (R-CHOP) has become the standard of care for elderly patients with diffuse large B-cell lymphoma. We aimed to ascertain if a dose-dense R-CHOP regimen administered every 2 weeks (R-CHOP14) was superior
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