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MedKoo Cat#: 146287 | Name: Zinquin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Zinquin is a fluorescent zinc ion (Zn²⁺) chelator and probe widely used in biological and biochemical research to detect and image intracellular zinc. It selectively binds free or loosely bound zinc ions and fluoresces upon complexation, allowing for visualization using fluorescence microscopy. The mechanism involves coordination of the zinc ion with nitrogen and sulfur donor atoms in the zinquin molecule, producing a strong fluorescent signal.

Chemical Structure

Zinquin
Zinquin
CAS#151606-29-0

Theoretical Analysis

MedKoo Cat#: 146287

Name: Zinquin

CAS#: 151606-29-0

Chemical Formula: C19H18N2O5S

Exact Mass: 386.0936

Molecular Weight: 386.42

Elemental Analysis: C, 59.06; H, 4.70; N, 7.25; O, 20.70; S, 8.30

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Zinquin;
IUPAC/Chemical Name
2-((2-methyl-8-((4-methylphenyl)sulfonamido)quinolin-6-yl)oxy)acetic acid
InChi Key
CGNKOBNGEFZRQU-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CC1=CC=C(C=C1)S(=O)(=O)NC2=CC(OCC(O)=O)=CC3=CC=C(C)N=C23
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 386.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Colvin RA, Laskowski M, Fontaine CP. Zinquin identifies subcellular compartmentalization of zinc in cortical neurons. Relation to the trafficking of zinc and the mitochondrial compartment. Brain Res. 2006 Apr 26;1085(1):1-10. doi: 10.1016/j.brainres.2006.02.043. Epub 2006 Apr 11. PMID: 16581038. 2: Coyle P, Zalewski PD, Philcox JC, Forbes IJ, Ward AD, Lincoln SF, Mahadevan I, Rofe AM. Measurement of zinc in hepatocytes by using a fluorescent probe, zinquin: relationship to metallothionein and intracellular zinc. Biochem J. 1994 Nov 1;303 ( Pt 3)(Pt 3):781-6. doi: 10.1042/bj3030781. PMID: 7980447; PMCID: PMC1137615. 3: Snitsarev V, Budde T, Stricker TP, Cox JM, Krupa DJ, Geng L, Kay AR. Fluorescent detection of Zn(2+)-rich vesicles with Zinquin: mechanism of action in lipid environments. Biophys J. 2001 Mar;80(3):1538-46. doi: 10.1016/S0006-3495(01)76126-7. PMID: 11222314; PMCID: PMC1301345. 4: Nowakowski AB, Petering DH. Reactions of the fluorescent sensor, Zinquin, with the zinc-proteome: adduct formation and ligand substitution. Inorg Chem. 2011 Oct 17;50(20):10124-33. doi: 10.1021/ic201076w. Epub 2011 Sep 9. PMID: 21905645; PMCID: PMC3230276. 5: Nowakowski AB, Meeusen JW, Menden H, Tomasiewicz H, Petering DH. Chemical- Biological Properties of Zinc Sensors TSQ and Zinquin: Formation of Sensor-Zn- Protein Adducts versus Zn(Sensor)2 Complexes. Inorg Chem. 2015 Dec 21;54(24):11637-47. doi: 10.1021/acs.inorgchem.5b01535. Epub 2015 Dec 9. PMID: 26650477. 6: Jansen S, Arning J, Dülcks T, Beyersmann D. S-Nitroso compounds interfere with zinc probing by Zinquin. Anal Biochem. 2004 Sep 1;332(1):145-52. doi: 10.1016/j.ab.2004.05.003. PMID: 15301959. 7: Nowakowski A, Petering D. Sensor specific imaging of proteomic Zn2+ with zinquin and TSQ after cellular exposure to N-ethylmaleimide. Metallomics. 2012 May;4(5):448-56. doi: 10.1039/c2mt00189f. Epub 2012 Apr 13. PMID: 22498931; PMCID: PMC3354649. 8: Zalewski PD, Forbes IJ, Seamark RF, Borlinghaus R, Betts WH, Lincoln SF, Ward AD. Flux of intracellular labile zinc during apoptosis (gene-directed cell death) revealed by a specific chemical probe, Zinquin. Chem Biol. 1994 Nov;1(3):153-61. doi: 10.1016/1074-5521(94)90005-1. PMID: 9383385. 9: Kimber MC, Mahadevan IB, Lincoln SF, Ward AD, Tiekink ER. The synthesis and fluorescent properties of analogues of the zinc(II) specific fluorophore zinquin ester. J Org Chem. 2000 Dec 1;65(24):8204-9. doi: 10.1021/jo000678x. PMID: 11101374. 10: Zalewski PD, Forbes IJ, Betts WH. Correlation of apoptosis with change in intracellular labile Zn(II) using zinquin [(2-methyl-8-p-toluenesulphonamido-6-quinolyloxy)acetic acid], a new specific fluorescent probe for Zn(II). Biochem J. 1993 Dec 1;296 ( Pt 2)(Pt 2):403-8. doi: 10.1042/bj2960403. PMID: 8257431; PMCID: PMC1137710. 11: Hendrickson KM, Geue JP, Wyness O, Lincoln SF, Ward AD. Coordination and fluorescence of the intracellular Zn2+ probe [2-methyl-8-(4-toluenesulfonamido)-6-quinolyloxy]acetic acid (Zinquin A) in ternary Zn2+ complexes. J Am Chem Soc. 2003 Apr 2;125(13):3889-95. doi: 10.1021/ja020685y. PMID: 12656623. 12: Zalewski PD, Jian X, Soon LL, Breed WG, Seamark RF, Lincoln SF, Ward AD, Sun FZ. Changes in distribution of labile zinc in mouse spermatozoa during maturation in the epididymis assessed by the fluorophore Zinquin. Reprod Fertil Dev. 1996;8(7):1097-105. doi: 10.1071/rd9961097. PMID: 8916286. 13: Meeusen JW, Nowakowski A, Petering DH. Reaction of metal-binding ligands with the zinc proteome: zinc sensors and N,N,N',N'-tetrakis(2-pyridylmethyl)ethylenediamine. Inorg Chem. 2012 Mar 19;51(6):3625-32. doi: 10.1021/ic2025236. Epub 2012 Mar 1. PMID: 22380934; PMCID: PMC3564517. 14: Suzuki M, Suzuki T, Watanabe M, Hatakeyama S, Kimura S, Nakazono A, Honma A, Nakamaru Y, Vreugde S, Homma A. Role of intracellular zinc in molecular and cellular function in allergic inflammatory diseases. Allergol Int. 2021 Apr;70(2):190-200. doi: 10.1016/j.alit.2020.09.007. Epub 2020 Oct 27. PMID: 33127267. 15: Ranaldi G, Perozzi G, Truong-Tran A, Zalewski P, Murgia C. Intracellular distribution of labile Zn(II) and zinc transporter expression in kidney and MDCK cells. Am J Physiol Renal Physiol. 2002 Dec;283(6):F1365-75. doi: 10.1152/ajprenal.00094.2002. Epub 2002 Aug 13. PMID: 12388418. 16: Truong-Tran AQ, Grosser D, Ruffin RE, Murgia C, Zalewski PD. Apoptosis in the normal and inflamed airway epithelium: role of zinc in epithelial protection and procaspase-3 regulation. Biochem Pharmacol. 2003 Oct 15;66(8):1459-68. doi: 10.1016/s0006-2952(03)00498-2. PMID: 14555222. 17: Sauer GR, Smith DM, Cahalane M, Wu LN, Wuthier RE. Intracellular zinc fluxes associated with apoptosis in growth plate chondrocytes. J Cell Biochem. 2003 Apr 1;88(5):954-69. doi: 10.1002/jcb.10446. PMID: 12616534. 18: Rolles B, Maywald M, Rink L. Intracellular zinc during cell activation and zinc deficiency. J Trace Elem Med Biol. 2021 Dec;68:126864. doi: 10.1016/j.jtemb.2021.126864. Epub 2021 Sep 20. PMID: 34562730. 19: Galiana-Roselló C, Aceves-Luquero C, González J, Martínez-Camarena Á, Villalonga R, Fernández de Mattos S, Soriano C, Llinares J, García-España E, Villalonga P, González-Rosende ME. Toward a Rational Design of Polyamine-Based Zinc-Chelating Agents for Cancer Therapies. J Med Chem. 2020 Feb 13;63(3):1199-1215. doi: 10.1021/acs.jmedchem.9b01554. Epub 2020 Jan 24. PMID: 31935092. 20: Yaduvanshi PS, Palika R, Pullakhandam R. A Fluorometric Method for Zinc Estimation: Applications in the Estimation of Plasma Zinc and in Assessing Zinc Bioaccessibility from Rice. Biol Trace Elem Res. 2025 Mar;203(3):1701-1708. doi: 10.1007/s12011-024-04277-3. Epub 2024 Jun 26. PMID: 38922542.

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