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| Targets |
Zinc ions (Zn2+). Zinquin primarily interacts with zinc ions to form fluorescent complexes. Upon binding to Zn2+, the probe undergoes a significant fluorescence enhancement, enabling sensitive detection of zinc concentrations. Zinquin forms either 1:1 or 2:1 (probe:Zn2+) complexes with dissociation constants (Kd) of 370 +/- 60 nM and 850 +/- 160 nM, respectively. The compound is selective for Zn2+ over other metal ions such as Ca2+, Mg2+, and Fe2+.
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| ln Vitro |
In vitro, Zinquin is used to detect and quantify zinc ions in solution and in biological samples. The probe exhibits UV excitation at 364-368 nm and blue emission at approximately 385-490 nm upon Zn2+ complexation. It is used in biochemical assays to measure zinc concentrations in cell lysates, biological fluids, and environmental samples. The compound's defined Kd values (370 nM and 850 nM) enable straightforward fluorescence-to-concentration calibration. Zinquin forms binary Zn(ZQ)2 complexes to extract Zn2+ from proteins, making it the preferred sensor for oxidative/nitrosative Zn2+-release assays.
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| ln Vivo |
In vivo, Zinquin is used to monitor intracellular zinc concentrations in living cells and tissues. The ethyl ester prodrug (Zinquin ethyl ester) is membrane-permeant and is hydrolyzed by intracellular esterases to generate the active Zinquin acid, enabling intracellular zinc imaging. It has been used to monitor changes in intracellular concentrations of Zn2+ in thymocytes and hepatocytes. Zinquin is widely utilized for detecting cellular zinc status and measuring Zn2+ concentrations within biological systems.
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| Enzyme Assay |
In vitro fluorescence assays for Zinquin measure zinc-dependent fluorescence enhancement. The probe is dissolved in appropriate buffer (e.g., HEPES, pH 7.4) at a concentration of 1-10 microM. Varying concentrations of Zn2+ (0-100 microM) are added to the probe solution, and fluorescence intensity is measured at excitation 364-368 nm and emission 385-490 nm using a fluorescence spectrophotometer or plate reader. A standard curve of fluorescence versus Zn2+ concentration is generated. For selectivity testing, other metal ions (Ca2+, Mg2+, Fe2+, Cu2+, etc.) are tested under the same conditions. Kd values are calculated from titration curves.
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| Cell Assay |
In vitro cell-based assays using Zinquin measure intracellular zinc concentrations. Cells are loaded with Zinquin ethyl ester (1-10 microM) in culture medium for 30-60 minutes at 37degC. After washing to remove extracellular probe, cells are incubated for an additional 30 minutes to allow de-esterification. Fluorescence is measured using a fluorescence microscope, flow cytometer, or plate reader (Ex/Em ~364/385 nm). Changes in intracellular zinc concentration are monitored by measuring fluorescence intensity over time. Zinc chelators (e.g., TPEN) or zinc ionophores (e.g., pyrithione) can be used as controls to confirm zinc-dependent fluorescence.
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| Animal Protocol |
In vivo animal studies using Zinquin are typically conducted in rodents. The Zinquin ethyl ester prodrug is administered via intraperitoneal or intravenous injection at doses of 1-10 mg/kg. After administration, animals are sacrificed at various time points, and tissues (liver, kidney, brain, pancreas) are collected for fluorescence imaging or homogenization and fluorometric analysis. Alternatively, intravital imaging can be performed in anesthetized animals using specialized microscopy setups. Changes in tissue zinc levels can be monitored in response to dietary manipulation, disease, or pharmacological interventions.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of Zinquin are characteristic of small-molecule fluorescent probes. With a molecular weight of 386.4 and moderate lipophilicity, the compound and its ethyl ester prodrug can cross cell membranes. The free acid form (Zinquin) is cell-impermeable and used for extracellular measurements, while the ethyl ester prodrug is membrane-permeant and hydrolyzed intracellularly to the active form. The probe is typically stored at -20degC protected from light. Zinquin exhibits UV excitation at 364-368 nm and blue emission at approximately 385-490 nm upon Zn2+ binding.
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| Toxicity/Toxicokinetics |
Toxicological data for Zinquin are limited as the compound is used as a research probe and not for therapeutic applications. The compound is generally considered to have low cytotoxicity at the concentrations used for fluorescence imaging (1-10 microM). Standard safety precautions for handling chemical compounds apply. The ethyl ester prodrug is hydrolyzed intracellularly to release the active Zinquin acid, which may have minimal cellular toxicity at working concentrations. Not approved for clinical use.
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| References | |
| Additional Infomation |
Zinquin is a research-grade fluorescent probe for zinc detection. Its synonyms include (2-methyl-8-p-toluenesulfonamido-6-quinolyloxy)acetic acid. The compound has a purity of ≥95% (HPLC) and is supplied as a solid. The free acid form is cell-impermeable and used for extracellular zinc detection, while the ethyl ester prodrug (CAS 181530-09-6) enables intracellular zinc imaging. Zinquin exhibits UV excitation at 364-368 nm and blue emission at approximately 385-490 nm upon Zn2+ complexation. It is widely used in zinc biology research to study zinc homeostasis and zinc-dependent cellular processes. Not approved for clinical use.
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| Molecular Formula |
C19H18N2O5S
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|---|---|
| Molecular Weight |
386.42162
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| Exact Mass |
386.093
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| CAS # |
151606-29-0
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| PubChem CID |
132933
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| Appearance |
White to off-white solid powder
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| Density |
1.412g/cm3
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| Boiling Point |
608ºC at 760 mmHg
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| Melting Point |
112-114ºC
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| Vapour Pressure |
1.23E-15mmHg at 25°C
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| Index of Refraction |
1.661
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| LogP |
4.748
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
27
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| Complexity |
612
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
CGNKOBNGEFZRQU-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H18N2O5S/c1-12-3-7-16(8-4-12)27(24,25)21-17-10-15(26-11-18(22)23)9-14-6-5-13(2)20-19(14)17/h3-10,21H,11H2,1-2H3,(H,22,23)
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| Chemical Name |
2-[2-methyl-8-[(4-methylphenyl)sulfonylamino]quinolin-6-yl]oxyacetic acid
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
DMSO : ~50 mg/mL (~129.39 mM)
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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 | 2.5879 mL | 12.9393 mL | 25.8786 mL | |
| 5 mM | 0.5176 mL | 2.5879 mL | 5.1757 mL | |
| 10 mM | 0.2588 mL | 1.2939 mL | 2.5879 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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