| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| Other Sizes |
Purity: ≥98%
| Targets |
Dequalinium Chloride targets mitochondria in carcinoma cells, acting as a mitochondrial poison by blocking mitochondrial enzymes, specifically the mitochondrial enzyme F1-ATPase via direct binding and subsequent inhibition. It also inhibits protein kinase C (PKC). [1]
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| ln Vitro |
Dequalinium chloride (DECA) is a cationic, lipophilic compound with structure similar to the dye rhodamine 123. DECA is selectively accumulated and retained within the mitochondria of carcinoma cells where it acts as a mitochondrial poison by blocking mitochondrial enzymes which can then disrupt cellular energy production, eventually resulting in cell death. Dequalinium Chloride is a blocker of ganglionic transmission (EC50 = 2 μM). Dequalinium is a potent inhibitor of apamin-sensitive K+ channels in hepatocytes and of nicotinic responses in skeletal muscle. Dequalinium blocks angiotensin II-evoked K+ loss with an IC50 of 1.5 μM and also inhibited125I - monoiodoapamin binding with Ki of 1.1 μM. Dequalinium produces a rapid and reversible inhibition of the slow apamin-sensitive component of the afterhyperpolarization (AHP) which follows a single action potential in cultured rat sympathetic neurons. Dequalinium Chloride (DECA) is a dicationic lipophilic PKC inhibitor. When exposed to UV light, DECA covalently binds to and irreversibly inhibits PKCα and PKCβ.
Cell Assay: DECA, as a mitochondrial poison, is an agent with capable of potentiating the effects of tumor necrosis factor against ovarian cancer cell lines. Dequalinium Chloride was previously shown by the authors to synergize the in vitro antitumor effects of tumor necrosis factor (TNF) against a panel of human ovarian cancer cell lines. However, no detailed in vitro experimental data (e.g., IC50, cell viability, apoptosis) are presented in this paper. The combination of Dequalinium Chloride and TNF resulted in enhanced tumor cell killing in vitro, as referenced from earlier studies (Manetta et al., 1990, 1991). [1] |
| ln Vivo |
In mice bearing bladder MB49 tumors, Dequalinium chloride (2 mg/kg/d, i.p.) displays anticarcinoma activity with T/C of 210%.
In the PA-1 human ovarian cancer xenograft model, treatment with single-agent Dequalinium Chloride (5 mg/kg every other day, IP) initiated 3 days post-tumor injection increased animal survival by 37% (P=0.002) compared to controls. When treatment was delayed until day 7 (histologically confirmed tumor), single-agent Dequalinium Chloride increased survival by 23% (P=0.04). In the UCI-101 ovarian tumor model (initiated day 6), single-agent Dequalinium Chloride increased survival by 28% (P=0.04). Sequential treatment with Dequalinium Chloride followed by TNF resulted in survival increases of 45% (PA-1, day 3, P=0.0002), 23% (PA-1, day 7, P=0.04), and 41% (UCI-101, P=0.003). No statistical differences were detected between single-agent Dequalinium Chloride and combination DECA+TNF except in the UCI-101 model, where the apparent potentiation was due to the stimulatory effects of TNF alone. [1] |
| Enzyme Assay |
The paper mentions that Dequalinium Chloride inhibits the mitochondrial enzyme F1-ATPase by direct binding (citing Zhou and Allison, 1988),[1]
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| Cell Assay |
The authors reference previous in vitro work showing that Dequalinium Chloride synergizes with TNF and interferon-gamma against human ovarian cancer cell lines, but the present paper focuses on in vivo studies and does not include any original cell-based experimental procedures or results. [1]
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| Animal Protocol |
Dissolved in water using a bath sonicator; 2 mg/kg; i.p. injection Mice bearing bladder MB49 tumors
Female Balb/c athymic nude mice (8-10 weeks old) were used. Ovarian cancer xenografts were established by intraperitoneal (IP) injection of 2.0 × 10^7 PA-1 or UCI-101 human ovarian cancer cells. Dequalinium Chloride was dissolved in sterile water using a water bath sonicator, and subsequent dilutions were prepared in physiological saline containing 0.2% fetal calf serum. For the PA-1 model, treatments were initiated either on day 3 (tumor implantation not histologically confirmed) or day 7 (histologically confirmed microscopic tumor implantation). For the UCI-101 model, treatments began on day 6 (histologically confirmed). Dequalinium Chloride was administered IP at a dose of 5 mg/kg every other day (qod). Combination treatment consisted of Dequalinium Chloride given on day 1, followed by TNF (recombinant human TNF-α, 0.5 μg/mouse) on the subsequent day; animals received only one drug per day. All mice received daily IP injections of either drug or vehicle (saline with 0.2% fetal calf serum, 0.5 ml/mouse) in alternating abdominal quadrants. Drug treatments were discontinued 60 days post-implantation. In the UCI-101 model, drugs were discontinued on day 56 due to observed toxicity. [1] |
| Toxicity/Toxicokinetics |
In the UCI-101 ovarian tumor model, drug treatment (including Dequalinium Chloride alone and in combination with TNF) was discontinued on day 56 due to toxicity, as noted in Figure 3 caption. No other specific toxicity data (e.g., LD50, hepatotoxicity, nephrotoxicity, protein binding) are provided in this paper. [1]
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| References | |
| Additional Infomation |
Dequalinium chloride is an organochloride, a dichloride of desquinammonia. It has various pharmacological effects, including use as a disinfectant, an inhibitor of mitochondrial NADH:ubiquinone reductase, an antifungal agent, and an antitumor agent. It contains desquinammonia. It is a topical antibacterial agent, available in various salt forms. It can be used in wound dressings and for the treatment of oral infections, and may also have antifungal activity, but may cause skin ulceration. See also: 2,4-dichlorophenoxyacetic acid (note moved to).
Dequalinium Chloride is a cationic, lipophilic compound structurally similar to rhodamine 123 but with two positive charges. It is used clinically as an antimicrobial agent in mouthwash and vaginal ointments. The compound selectively accumulates in the mitochondria of carcinoma cells due to the high negative membrane electric potential of carcinoma plasma membranes and the high mitochondrial membrane potential. This selectivity provides carcinoma-specific cytotoxicity with reduced normal tissue toxicity. Dequalinium Chloride has been shown to be more effective than cisplatin, 5-fluorouracil, vinblastine, methotrexate, bleomycin, or cyclophosphamide in certain animal models (e.g., MB49 bladder carcinoma, human colon carcinoma CX-1). In a rat colon tumor isograft model, Dequalinium Chloride significantly inhibited primary tumor growth. The compound also demonstrated activity against human ovarian xenografts in athymic mice. Its mechanisms of action include inhibition of mitochondrial ATP synthesis (specifically F1-ATPase), disruption of cellular energy production, and inhibition of protein kinase C and calmodulin. [1] |
| Molecular Formula |
C30H40N4.2CL
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| Molecular Weight |
527.57
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| Exact Mass |
526.263
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| CAS # |
522-51-0
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| Related CAS # |
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| PubChem CID |
10649
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| Appearance |
Off-white to light yellow solid powder
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| Melting Point |
≥300 °C(lit.)
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| LogP |
1.34
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
11
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| Heavy Atom Count |
36
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| Complexity |
532
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[Cl-].[Cl-].[N+]1(=C(C([H])([H])[H])C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)N([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[N+]1=C(C([H])([H])[H])C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)N([H])[H]
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| InChi Key |
LTNZEXKYNRNOGT-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
1,1-(decane-1,10-diyl)bis(4-amino-2-methylquinolin-1-ium) chloride
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.8955 mL | 9.4774 mL | 18.9548 mL | |
| 5 mM | 0.3791 mL | 1.8955 mL | 3.7910 mL | |
| 10 mM | 0.1895 mL | 0.9477 mL | 1.8955 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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