An acridine compound with diverse biological activities and cell labeling properties
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Quinacrine (hydrochloride hydrate)

Item No. 15041

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine, dihydrochloride hydrate
Synonyms
  • Atebrine
  • Mepacrine
Molecular Formula
C23H30ClN3O • 2HCl [XH2O]
Formula Weight
472.9
Purity
≥95%
Emission
525 nm (DNA and RNA), 470-580 nm (acidic vesicles/lysosomes)
Excitation
436 nm (DNA and RNA), 458 nm (acidic vesicles/lysosomes)
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 5 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
223, 283, 346, 427, 449 nm
SMILES
ClC1=CC=C2C(NC(C)CCCN(CC)CC)=C3C(C=CC(OC)=C3)=NC2=C1.Cl.Cl.O
InChi Code
InChI=1S/C23H30ClN3O.2ClH.H2O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23;;;/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);2*1H;1H2
InChi Key
NJIQZEZRCQCCKR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Quinacrine is an acridine compound with diverse biological activities that has also been used as a stain for DNA and RNA in fixed cells and for fluorescent tracking of acidic vesicles, such as lysosomes, in live cells.1,2,3,4 It has anti-protozoal properties, potently prevents misfolding of prion protein (EC50 = 0.3 μM), blocks voltage-dependent sodium channels (IC50 = 3.3 μM), and inhibits aldehyde oxidase (IC50 = 3.3 μM).1,2,3,4 Quinacrine is also an effective riboflavin antagonist, associating with the riboflavin-binding protein (Ki = 6.7 μM), and an inhibitor of P-glycoprotein (EC50 = 14.4 μM).5,6 At much higher doses, quinacrine inhibits phospholipase A2 activity.7,8 Quinacrine binds to nucleic acids and has been used in fixed cells to stain DNA and RNA with excitation/emission maxima of 436/525 nm, respectively.9 In live cells, it is taken up into acidic vesicles, such as lysosomes, and can be used to for long-term imaging with an excitation of 458 nm and emission in the 470-580 nm range.10

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Upcroft, P., and Upcroft, J.A. Drug targets and mechanisms of resistance in the anaerobic protozoa. Clin. Microbiol. Rev. 14(1), 150-164 (2001).

    2. Vogtherr, M., Grimme, S., Elshorst, B., et al. Antimalarial drug quinacrine binds to C-terminal helix of cellular prion protein. J. Med. Chem. 46(17), 3563-3564 (2003).

    3. McNeal, E.T., Lewandowski, G.A., Daly, J.W., et al. [3H]Batrachotoxinin A 20α-benzoate binding to voltage-sensitive sodium channels: A rapid and quantitative assay for local anesthetic activity in a variety of drugs. J. Med. Chem. 28(3), 381-388 (1985).

    4. Pryde, D.C., Dalvie, D., Hu, Q., et al. Aldehyde oxidase: An enzyme of emerging importance in drug discovery. J. Med. Chem. 53(24), 8441-8460 (2010).

    5. Plantinga, A., Witte, A., Li, M.H., et al. Bioanalytical screening of riboflavin antagonists for targeted drug delivery - A thermodynamic and kinetic study. ACS Med. Chem. Lett. 2(5), 363-367 (2011).

    6. Tiberghien, F., and Loor, F. Ranking of P-glycoprotein substates and inhibitors by a calcein-AM fluorometry screening assay. Anticancer Drugs 7(5), 568-578 (1996).

    7. Farooqui, A.A., Ong, W.Y., and Horrocks, L.A. Inhibitors of brain phospholipase A2 activity: Their neuropharmacological effects and therapeutic importance for the treatment of neurologic disorders. Pharmacol. Rev. 58(3), 591-620 (2006).

    8. Caro, A.A., and Cederbaum, A.I. Role of phospholipase A2 activation and calcium in CYP2E1-dependent toxicity in HepG2 cells. The Journal of Biological Chemisty 278(36), 33866-33877 (2003).

    9. Kasten, F.H. Table 2.3. Fluorescent and Luminescent Probes for Biological Activity: A Practical Guide to Technology for Quantitative Real-Time Analysis 33 (1999).

    10. Pierzyńska-Mach, A., Janowski, P.A., and Dobrucki, J.W. Evaluation of acridine orange, LysoTracker Red, and quinacrine as fluorescent probes for long-term tracking of acidic vesicles. Cytometry A. 85(8), 729-737 (2014).