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V8879

Sigma-Aldrich

Vincristin -sulfat (Salz)

95.0-105.0% (HPLC), powder or crystals

Synonym(e):

22-Oxo-vincaleukoblastin -sulfat (Salz), Leurocristin -sulfat (Salz), VCR

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About This Item

Empirische Formel (Hill-System):
C46H56N4O10 · H2SO4
CAS-Nummer:
2068-78-2
Molekulargewicht:
923.04
Beilstein:
3924631
EG-Nummer:
218-190-0
MDL-Nummer:
MFCD00084729
UNSPSC-Code:
51101500
PubChem Substanz-ID:
57654729
NACRES:
NA.85

Biologische Quelle

Streptomyces roseosporus

Qualitätsniveau

200

Assay

95.0-105.0% (HPLC)

Form

powder or crystals

Lagerbedingungen

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

Farbe

white to light yellow

Wirkungsspektrum von Antibiotika

neoplastics

Wirkungsweise

protein synthesis | interferes

Lagertemp.

−20°C

SMILES String

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

InChIKey

AQTQHPDCURKLKT-PNYVAJAMSA-N

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Anwendung

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) .

Biochem./physiol. Wirkung

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.

Hinweis zur Analyse

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

Sonstige Hinweise

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

Piktogramme

Skull and crossbonesHealth hazard
GHS06,GHS08

Signalwort

Danger

Gefahreneinstufungen

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Millipore

677175-M

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Etoposid synthetic, 95.0-105.0%, powder

Sigma-Aldrich

E1383

Etoposid

Cyclophosphamid Monohydrat bulk package

Sigma-Aldrich

C0768

Cyclophosphamid Monohydrat

Sigma-Aldrich

Sigma-Aldrich

T3077

TRO 19622

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
A Jordan et al.
Medicinal research reviews, 18(4), 259-296 (1998-07-17)
Tubulin is the biochemical target for several clinically used anticancer drugs, including paclitaxel and the vinca alkaloids vincristine and vinblastine. This review describes both the natural and synthetic agents which are known to interact with tubulin. Syntheses of the more
Patrick J Stiff et al.
The New England journal of medicine, 369(18), 1681-1690 (2013-11-01)
The efficacy of autologous stem-cell transplantation during the first remission in patients with diffuse, aggressive non-Hodgkin's lymphoma classified as high-intermediate risk or high risk on the International Prognostic Index remains controversial and is untested in the rituximab era. We treated
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