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Merck
CN

D3768

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)
UNSPSC Code:
12352200
PubChem Substance ID:
24278367
EC Number:
208-330-9
MDL number:
MFCD10567439
Assay:
≥95% (titration)
Form:
powder

Key Documents

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InChI key

CZCJAGQJOXJBST-UHFFFAOYSA-N

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

SMILES string

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

assay

≥95% (titration)

form

powder

mp

≥300 °C (lit.)

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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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBT7670
BCBQ8545V
BCBQ8545
BCBL6312V
BCBL6312

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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)
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
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
Pilar Sancho et al.
Experimental biology and medicine (Maywood, N.J.), 237(8), 933-942 (2012-08-10)
Delocalized lipophilic cations, such as dequalinium (DQA), selectively accumulate in mitochondria and display anticancer activity in cells from different malignancies. Previous studies in K562 human leukemic cells indicate that DQA causes cell damage as a consequence of an early disturbance
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