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D3768

Sigma-Aldrich

Dequaliniumchlorid Hydrat

≥95% (titration)

Synonym(e):

1,1′-Decamethylen-bis-(4-amino-chinaldinium)-dichlorid Hydrat

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About This Item

Empirische Formel (Hill-System):
C30H40Cl2N4 · xH2O
CAS-Nummer:
1255077-34-9
Molekulargewicht:
527.57 (anhydrous basis)
EG-Nummer:
208-330-9
MDL-Nummer:
MFCD10567439
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278367

Assay

≥95% (titration)

Form

powder

mp (Schmelzpunkt)

≥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

InChIKey

CZCJAGQJOXJBST-UHFFFAOYSA-N

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Biochem./physiol. Wirkung

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.

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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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