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V1377

Sigma-Aldrich

Vinblastine sulfate salt

≥97% (HPLC)

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Synonym(s):
VLB, Vincaleukoblastine sulfate salt
Empirical Formula (Hill Notation):
C46H58N4O9 · H2SO4
CAS Number:
Molecular Weight:
909.05
Beilstein:
3659812
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥97% (HPLC)

form

(powder or amorphous or crystalline powder)

color

white to light yellow

mp

267 °C (dec.) (lit.)

absorption

14 at 270 nm in 0.1 M phosphate buffer at 1 mM
16.2 at 259 nm in ethanol at 1 mM
53.7 at 214 nm in ethanol at 1 mM

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes

originator

Eli Lilly

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.[H][C@@]12CN(CCc3c([nH]c4ccccc34)[C@@](C1)(C(=O)OC)c5cc6c(cc5OC)N(C)[C@@]7([H])[C@](O)([C@H](OC(C)=O)[C@]8(CC)C=CCN9CC[C@]67[C@]89[H])C(=O)OC)C[C@](O)(CC)C2

InChI

1S/C46H58N4O9.H2O4S/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7;1-5(2,3)4/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3;(H2,1,2,3,4)/t28-,37-,38+,39+,42-,43+,44+,45-,46-;/m0./s1

InChI key

KDQAABAKXDWYSZ-PNYVAJAMSA-N

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This Item
V8879A0384H8759
Arcaine sulfate salt

Sigma-Aldrich

A0384

Arcaine sulfate salt

form

(powder or amorphous or crystalline powder)

form

powder or crystals

form

powder

form

powder

color

white to light yellow

color

white to light yellow

color

-

color

off-white

originator

Eli Lilly

originator

-

originator

-

originator

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

Application

Vinblastine sulfate salt has been used:
  • as a microtubule depolymerizing drug for the synchronization of human cell lines in G2/M phase
  • as a multidrug resistance screening substrate in human colon cancer cell line (HCT116) cell line
  • as an antimicrotubule agent in sub perineural glia of Drosophila brain

Biochem/physiol Actions

Plant alkaloid that inhibits microtubule assembly by binding tubulin and inducing self-association in spiral aggregates in a reaction that appears to be regulated by the C-terminus of β-tubulin and is enhanced by GDP and GTP. Depolymerizes microtubules. Arrests the cell cycle in G2/M-phase by blocking mitotic spindle formation. Triggers Raf-1 activation, phosphorylation of bcl-2-family proteins, induction of p53 expression, and apoptosis in several tumor cell lines. Substrate of Pgp and CYP3A4.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Muta. 2 - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


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Use of drugs to study role of microtubule assembly dynamics in living cells.
M A Jordan et al.
Methods in enzymology, 298, 252-276 (1998-09-30)
DrugTargetSeqR: a genomics-and CRISPR-Cas9-based method to analyze drug targets
Kasap C, et al.
Nature chemical biology, 10(8), 626-626 (2014)
Phosphorylation of mixed lineage leukemia 5 by CDC2 affects its cellular distribution and is required for mitotic entry
Liu J, et al.
The Journal of Biological Chemistry, 285(27), 20904-20914 (2010)
M V Blagosklonny et al.
Cancer research, 57(1), 130-135 (1997-01-01)
Recent studies have shown that paclitaxel leads to activation of Raf-1 kinase and have suggested that this activation is essential for bcl-2 phosphorylation and apoptosis. In the present study, we demonstrate that, in addition to paclitaxel, other agents that interact
Evolutionary conservation of vertebrate blood-brain barrier chemoprotective mechanisms in Drosophila
Mayer F, et al.
The Journal of Neuroscience, 29(11), 3538-3550 (2009)

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