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V1377

Sigma-Aldrich

Vinblastine sulfate salt

≥97% (HPLC), powder, plant alkaloid

Synonym(s):

VLB, Vincaleukoblastine sulfate salt

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About This Item

Empirical Formula (Hill Notation):
C46H58N4O9 · H2SO4
CAS Number:
143-67-9
Molecular Weight:
909.05
Beilstein/REAXYS Number:
3659812
EC Number:
205-606-0
MDL number:
MFCD00082457
UNSPSC Code:
12352200
PubChem Substance ID:
24278771
NACRES:
NA.77

Key Documents

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Product Name

Vinblastine sulfate salt, 96-102% (HPLC)

Quality Level

200

assay

96-102% (HPLC)

form

powder

color

white to light yellow

mp

267 °C (dec.) (lit.)

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

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

Gene Information

human ... TBCC(6903), TUBA1A(7846), TUBA1B(10376), TUBA1C(84790), TUBA3C(7278), TUBA3E(112714), TUBA4A(7277), TUBB(203068), TUBB1(81027), TUBB2A(7280), TUBB2B(347733), TUBB3(10381), TUBB4A(10382), TUBB4B(10383), TUBB6(84617), TUBB8(347688)

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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

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
108M4181V
078M4002V
079M4084V
039M4086V
028M4095V

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DrugTargetSeqR: a genomics-and CRISPR-Cas9-based method to analyze drug targets
Kasap C, et al.
Nature chemical biology, 10(8), 626-626 (2014)
X R Zhou-Pan et al.
Cancer research, 53(21), 5121-5126 (1993-11-01)
Vinblastine biotransformation was investigated by using a human liver microsomes library. The drug was converted into one major metabolite (M) upon incubation with the microsomes. A large interindividual variation in vinblastine metabolism was observed among the samples tested, with a
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)
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)
Mariann Molnár et al.
Scientific reports, 9(1), 14284-14284 (2019-10-05)
In the last decade, avian gene preservation research has focused on the use of the early precursors of the reproductive cells, the primordial germ cells (PGCs). This is because avian PGCs have a unique migration route through the vascular system
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