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D3768

Sigma-Aldrich

Dequalinium chloride hydrate

≥95% (titration)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C30H40Cl2N4 · xH2O
CAS Number:
1255077-34-9
Molecular Weight:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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)
Diana Lyrawati et al.
Pharmaceutical research, 28(11), 2848-2862 (2011-08-13)
We describe a novel strategy for expression of GFP in mammalian mitochondria. The key components of the strategy were an artificially created mitochondrial genome pmtGFP and a DQAsome transfection system. Using immunofluorescence and a combination of immunohistochemical and molecular based
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