[2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol Chemical Properties

Melting point:

198-199.5 °C

Boiling point:

551.4±50.0 °C(Predicted)

Density 

1.244±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 10 mg/ml; DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml; DMSO: 1 mg/ml; Ethanol: 0.25 mg/ml

form 

A crystalline solid

pka

13.22±0.20(Predicted)

color 

white to beige

InChI

1S/C21H21ClN2O/c22-15-10-8-14(9-11-15)20-13-17(16-5-1-2-6-18(16)24-20)21(25)19-7-3-4-12-23-19/h1-2,5-6,8-11,13,19,21,23,25H,3-4,7,12H2

InChIKey

VKLJPGAHSLIQKH-UHFFFAOYSA-N

SMILES

Clc1ccc(cc1)c2nc3c(c(c2)C(O)C4NCCCC4)cccc3

Safety Information

WGK Germany 

WGK 3

HS Code 

2933499090

Storage Class

11 - Combustible Solids

[2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol Usage And Synthesis

Description

Vacquinols are a new class of quinine-derivatives that stimulate death in glioblastoma cells by massive macropinocytotic vacuolization, ATP depletion, and cytoplasmic membrane rupture. A key effector of vacquinols is MAPK kinase 4 (MKK4). Vacquinol-1 is an activator of MKK4-dependent macropinocytotic cell death in glioblastoma cells. It induces ATP depletion in glioblastoma cells (IC₅₀ = 3.14 μM at 1 day) without affecting fibroblasts, embryonic stem cells, or osteosarcoma cells. Vacquinol-1 is orally bioavailable with good brain penetrance and excellent pharmacokinetics. Oral administration of vacquinol-1 (20 mg/kg once daily for five days) substantially impairs the growth of engrafted glioblastoma cell tumors in mice and prolongs survival.

Uses

Vacquinol-1 is in the vacquinol class of quinine derivatives that stimulate death in glioblastoma cells through massive macropinocytotic vacuolization, ATP depletion and eventual cytoplasmic membrane rupture.

References

[1] SATISH SRINIVAS KITAMBI. RETRACTED: Vulnerability of glioblastoma cells to catastrophic vacuolization and death induced by a small molecule.[J]. Cell, 2014, 157 2: 313-328. DOI: 10.1016/j.cell.2014.02.021

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