| Identification | Back Directory | [Name]
[2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol | [CAS]
5428-80-8 | [Synonyms]
CS-2185
NSC13316
NSC-13316
NSC 13316
Vacquinol-1
Vacquinol-1（NSC13316）
NSC 13316;NSC13316;NSC-13316;VACQUINOL 1;VACQUINOL1
[2-(4-chlorophenyl)quinolin-4-yl]-(2-piperidyl)methanol
4-Quinolinemethanol,2-(4-chlorophenyl)-a-2-piperidinyl-
4-Quinolinemethanol, 2-(4-chlorophenyl)-α-2-piperidinyl- | [Molecular Formula]
C21H21ClN2O | [MDL Number]
MFCD29918839 | [MOL File]
5428-80-8.mol | [Molecular Weight]
352.86 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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