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D3768

Sigma-Aldrich

Dequalinium chloride hydrate

≥95% (titration)

Sinónimos:

1,1′-Decamethylenebis(4-aminoquinaldinium) dichloride hydrate

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About This Item

Fórmula empírica (notación de Hill):
C30H40Cl2N4 · xH2O
Número de CAS:
1255077-34-9
Peso molecular:
527.57 (anhydrous basis)
EC Number:
208-330-9
MDL number:
MFCD10567439
UNSPSC Code:
12352200
PubChem Substance ID:
24278367

assay

≥95% (titration)

form

powder

mp

≥300 °C (lit.)

SMILES string

O.[Cl-].[Cl-].Cc1cc(N)c2ccccc2[n+]1CCCCCCCCCC[n+]3c(C)cc(N)c4ccccc34

InChI

1S/C30H38N4.2ClH.H2O/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34;;;/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H;1H2

InChI key

CZCJAGQJOXJBST-UHFFFAOYSA-N

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Biochem/physiol Actions

Dequalinium chloride is a selective blocker of apamin-sensitive K+ channels and inhibitor of XIAP (X-linked inhibitor of apoptosis protein). Has been shown to induce cytotoxicity in human acute promyelocytic leukemia NB4 cells through disturbance of mitochondrial function, oxidative stress, and downregulation of Raf/MEK/ERK and PI3K/Akt signaling pathways.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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S A Rotenberg et al.
The Journal of biological chemistry, 273(4), 2390-2395 (1998-01-27)
1,1'-Decamethylenebis-4-aminoquinaldinium diiodide (DECA; dequalinium) is an anti-tumor agent and protein kinase C (PKC) inhibitor whose mechanism of action with PKC is unknown. This study reports that with human PKC alpha, DECA exhibited competitive inhibition (Ki = 11.5 +/- 5 microM)
Tarek Zaidieh et al.
BMC cancer, 19(1), 1224-1224 (2019-12-18)
Mitochondria are considered a primary intracellular site of reactive oxygen species (ROS) generation. Generally, cancer cells with mitochondrial genetic abnormalities (copy number change and mutations) have escalated ROS levels compared to normal cells. Since high levels of ROS can trigger
L J Bock et al.
Letters in applied microbiology, 66(5), 368-377 (2018-02-13)
The effectiveness of several cationic disinfectants as well as colistin and polymyxin B were assessed under different growth conditions against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa strains. These conditions included different media (MH1, MH2, TSB and LB) and plate
Leah Mursaleen et al.
Journal of Parkinson's disease, 10(1), 99-111 (2019-12-24)
Reduced glutathione and excess free iron within dopaminergic, substantia nigra neurons in Parkinson's disease (PD) can drive accumulation of toxic hydroxyl radicals resulting in sustained oxidative stress and cellular damage. Factors such as brain penetrance and bioavailability have limited the
Kristen M Smith et al.
EMBO molecular medicine, 2(9), 371-384 (2010-08-20)
Neuroblastoma (NB) is the most deadly extra-cranial solid tumour in children necessitating an urgent need for effective and less toxic treatments. One reason for the lack of efficacious treatments may be the inability of existing drugs to target the tumour-initiating
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