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Dequalinium Chloride

anti-tumor agent and PKC inhibitor CAS# 522-51-0

Dequalinium Chloride

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Chemical structure

Dequalinium Chloride

3D structure

Chemical Properties of Dequalinium Chloride

Cas No. 522-51-0 SDF Download SDF
PubChem ID 10649 Appearance Powder
Formula C30H40Cl2N4 M.Wt 527.57
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : < 1 mg/mL (insoluble or slightly soluble)
Ethanol : < 1 mg/mL (insoluble)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 1-[10-(4-amino-2-methylquinolin-1-ium-1-yl)decyl]-2-methylquinolin-1-ium-4-amine;dichloride
SMILES CC1=[N+](C2=CC=CC=C2C(=C1)N)CCCCCCCCCC[N+]3=C(C=C(C4=CC=CC=C43)N)C.[Cl-].[Cl-]
Standard InChIKey LTNZEXKYNRNOGT-UHFFFAOYSA-N
Standard InChI InChI=1S/C30H38N4.2ClH/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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Dequalinium Chloride

DescriptionA potent and selective non-peptide blocker of the apamin-sensitive small conductance Ca2+-activated K+ channel (IC50 = 1.1 mM).

Dequalinium Chloride Dilution Calculator

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Dequalinium Chloride Molarity Calculator

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Preparing Stock Solutions of Dequalinium Chloride

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8955 mL 9.4774 mL 18.9548 mL 37.9097 mL 47.3871 mL
5 mM 0.3791 mL 1.8955 mL 3.791 mL 7.5819 mL 9.4774 mL
10 mM 0.1895 mL 0.9477 mL 1.8955 mL 3.791 mL 4.7387 mL
50 mM 0.0379 mL 0.1895 mL 0.3791 mL 0.7582 mL 0.9477 mL
100 mM 0.019 mL 0.0948 mL 0.1895 mL 0.3791 mL 0.4739 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Dequalinium Chloride

Dequalinium Chloride (DECA) is a PKC inhibitor with IC50 of 7-18 μM, and also a selective blocker of apamin-sensitive K+ channels with IC50 of 1.1 μM [1][3].
Protein kinase C (PKC) is a monomeric Ca2+- and phospholipid-dependent Ser/Thr protein kinases, it plays a critical role in growth factor-activated signaling and malignant transformation [1].
DECA is an anti-tumor agent and PKC inhibitor. It is selectively accumulated and retained within the mitochondria of carcinoma cells where it blocked mitochondrial enzymes which can then disrupt cellular energy production, eventually resulting in cell death [2]. Dequalinium is a potent inhibitor of apamin-sensitive K+ channels in hepatocytes and of nicotinic responses in skeletal muscle. Dequalinium blocked angiotensin II-evoked K+ loss with an IC50 value of 1.5 μM and also inhibited 125I - monoiodoapamin binding with Ki of 1.1 μM [3].
DECA, as a mitochondrial poison, is an agent with capable of potentiating the effects of tumor necrosis factor against ovarian cancer cell lines. DECA treatment can prolong animal survival in mice bearing the PA-1 intraperitoneal ovarian carcinoma xenograft. Single agent DECA increased animal survival by 37% whereas human TNF increased survival by 12% in those animals treated 3 days post tumor injection. DECA/TNF enhanced animal survival by 45% in treated animals [4].
References:
[1]. Rotenberg SA, Sun XG. Photoinduced inactivation of protein kinase C by dequalinium identifies the RACK-1-binding domain as a recognition site. J Biol Chem, 1998, 273(4): 2390-2395.
[2]. Manetta A, Emma D, Gamboa G, et al. Failure to enhance the in vivo killing of human ovarian carcinoma by sequential treatment with dequalinium chloride and tumor necrosis factor. Gynecol Oncol, 1993, 50(1): 38-44.
[3]. Castle NA, Haylett DG, Morgan JM, et al. Dequalinium: a potent inhibitor of apamin-sensitive K+ channels in hepatocytes and of nicotinic responses in skeletal muscle. Eur J Pharmacol, 1993, 236(2): 201-207.
[4]. Manetta A, Emma D, Fuchtner C, et al. Effect of recombinant human tumor-necrosis-factor-alpha and dequalinium chloride on human ovarian-cancer cell-lines in-vitro. Int J Oncol, 1993, 3(1): 127-33.

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References on Dequalinium Chloride

Use of locally delivered dequalinium chloride in the treatment of vaginal infections: a review.[Pubmed:26506926]

Arch Gynecol Obstet. 2016 Mar;293(3):469-84.

BACKGROUND: Vaginal infections are responsible for a large proportion of gynaecological outpatient visits. Those are bacterial vaginosis (BV), vulvovaginal candidosis (VVC), aerobic vaginitis (AV) associated with aerobic bacteria, and mixed infections. Usual treatments show similar acceptable short-term efficacy, but frequent recurrences and increasing microbial resistance are unsolved issues. Furthermore, vaginal infections are associated with a variety of serious adverse outcomes in pregnancy and generally have a major impact on quality of life. Identifying the correct therapy can be challenging for the clinician, particularly in mixed infections. FINDINGS: Dequalinium Chloride (DQC) is an anti-microbial antiseptic agent with a broad bactericidal and fungicidal activity. Systemic absorption after vaginal application of DQC is very low and systemic effects negligible. Vaginal DQC (Fluomizin vaginal tablets) has been shown to have equal clinical efficacy as clindamycin in the treatment of BV. Its broad antimicrobial activity makes it appropriate for the treatment of mixed vaginal infections and in case of uncertain diagnosis. Moreover, resistance of pathogens is unlikely due to its multiple mode of action, and vaginal DQC provides also a reduced risk for post-treatment vaginal infections. CONCLUSIONS: Vaginal DQC (10 mg) as 6-day therapy offers a safe and effective option for empiric therapy of different vaginal infections in daily practice. This review summarizes the available and relevant pharmacological and clinical data for the therapy of vaginal infections with vaginal DQC and provides the rationale for its use in daily gynaecologic practice.

Determination for micro amounts of nucleic acids by a resonance light scattering technique with dequalinium chloride.[Pubmed:18968413]

Talanta. 2001 Oct 31;55(4):669-75.

Based on the strong enhancement effect of nucleic acids on resonance light scattering of Dequalinium Chloride, the determination method for micro amounts of nucleic acids has been developed. Under the experimental conditions (5.0x10(-5) mol l(-1) dequalinium, pH 7.0, at room temperature) the linear range of this assay is 0.04-10.0 mug ml(-1) for calf thymus DNA and fish sperm DNA, and 0.04-35.0 mug ml(-1) for yeast RNA. The detection limits (3sigma) are 6.2 ng ml(-1) for calf thymus DNA, 7.4 ng ml(-1) for fish sperm DNA, and 7.0 ng ml(-1) for yeast RNA, respectively. Almost no interference can be observed from ionic strength, proteins, nucleoside, and most of the metal ions. Six synthetic samples were determined satisfactorily.

Susceptibility testing of Atopobium vaginae for dequalinium chloride.[Pubmed:22429611]

BMC Res Notes. 2012 Mar 19;5:151.

BACKGROUND: Atopobium vaginae and Gardnerella vaginalis are major markers for bacterial vaginosis. We aimed to determine the MIC and MBC range of the broad-spectrum anti-infective and antiseptic Dequalinium Chloride for 28 strains, belonging to 4 species of the genus Atopobium, i.e. A. vaginae, A. minutum, A. rimae and A. parvulum. METHODS: The MIC was determined with a broth microdilution assay. RESULTS: The MIC and MBC for Atopobium spp. for Dequalinium Chloride ranged between < 0.0625 and 2 mug/ml. CONCLUSIONS: This study demonstrated that Dequalinium Chloride inhibits and kills clinical isolates of A. vaginae at concentrations similar to those of clindamycin and lower than those of metronidazole.

A comparison of dequalinium chloride vaginal tablets (Fluomizin(R)) and clindamycin vaginal cream in the treatment of bacterial vaginosis: a single-blind, randomized clinical trial of efficacy and safety.[Pubmed:22205034]

Gynecol Obstet Invest. 2012;73(1):8-15.

AIMS: To investigate if vaginal application of Dequalinium Chloride (DQC, Fluomizin(R)) is as effective as vaginal clindamycin (CLM) in the treatment of bacterial vaginosis (BV). METHODS: This was a multinational, multicenter, single-blind, randomized trial in 15 centers, including 321 women. They were randomized to either vaginal DQC tablets or vaginal CLM cream. Follow-up visits were 1 week and 1 month after treatment. Clinical cure based on Amsel's criteria was the primary outcome. Secondary outcomes were rate of treatment failures and recurrences, incidence of post-treatment vulvovaginal candidosis (VVC), lactobacillary grade (LBG), total symptom score (TSC), and safety. RESULTS: Cure rates with DQC (C1: 81.5%, C2: 79.5%) were as high as with CLM (C1: 78.4%, C2: 77.6%). Thus, the treatment with DQC had equal efficacy as CLM cream. A trend to less common post-treatment VVC in the DQC-treated women was observed (DQC: 2.5%, CLM: 7.7%; p = 0.06). Both treatments were well tolerated with no serious adverse events occurring. CONCLUSION: Vaginal DQC has been shown to be equally effective as CLM cream, to be well tolerated with no systemic safety concerns, and is therefore a valid alternative therapy for women with BV [ClinicalTrials.gov, Med380104, NCT01125410].

Description

Dequalinium Chloride is a selective blocker of apamin-sensitive K+ channels.

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