A fluorescent dye
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3,3′-Diethyloxacarbocyanine (iodide)

Item No. 39456

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-ethyl-2-[3-(3-ethyl-2(3H)-benzoxazolylidene)-1-propen-1-yl]-benzoxazolium, monoiodide
CAS Number
905-96-4
Synonyms
  • DiOC2(3)
  • DOC
  • NK 85
Molecular Formula
C21H21N2O2 • I
Formula Weight
460.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly solubleDMSO: SolubleWater: Slightly soluble
SMILES
CCN1C2=CC=CC=C2OC1=CC=CC(OC3=CC=CC=C43)=[N+]4CC.[I-]
InChi Code
InChI=1S/C21H21N2O2.HI/c1-3-22-16-10-5-7-12-18(16)24-20(22)14-9-15-21-23(4-2)17-11-6-8-13-19(17)25-21;/h5-15H,3-4H2,1-2H3;1H/q+1;/p-1
InChi Key
FIZZUEJIOKEFFZ-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    3,3′-Diethyloxacarbocyanine (DiOC2(3)) is a cationic fluorescent dye that has been used to monitor mammalian and bacterial membrane potential.1,2,3,4 Upon cell hyperpolarization, it enters cells, and exhibits a decrease in fluorescence intensity and shift in emission from 530 nm to 670 nm upon excitation at 488 nm.4 DiOC2(3) selectively inhibits bovine heart mitochondrial complex I, also known as NADH dehydrogenase (IC50 = 9 µM), over bovine heart mitochondrial complex IV, also known as cytochrome c oxidase, and P. denitrificans mitochondrial complex I but activates bovine heart mitochondrial complex II, also known as succinate dehydrogenase, at 10 µM.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sims, P.J., Waggoner, A.S., Wang, C.H., et al. Studies on the mechanism by which cyanine dyes measure membrane potential in red blood cells and phosphatidylcholine vesicles. Biochemistry 13(16), 3315-3330 (1974).

    2. Gentry, D.R., Wilding, I., Johnson, J.M., et al. A rapid microtiter plate assay for measuring the effect of compounds on Staphylococcus aureus membrane potential. J. Microbiol. Methods 83(2), 254-256 (2010).

    3. Novo, D., Perlmutter, N.G., Hunt, R.H., et al. Accurate flow cytometric membrane potential measurement in bacteria using diethyloxacarbocyanine and a ratiometric technique. Cytometry 35(1), 55-63 (1999).

    4. Boi, P., Manti, A., Pianetti, A., et al. Evaluation of Escherichia coli viability by flow cytometry: A method for determining bacterial responses to antibiotic exposure. Cytometry B Clin. Cytom. 88(3), 149-153 (2015).

    5. Anderson, W.M., Wood, J.M., and Anderson, A.C. Inhibition of mitochondrial and Paracoccus denitrificans NADH-ubiquinone reductase by oxacarbocyanine dyes. A structure-activity study. Biochem. Pharmacol. 45(10), 2115-2122 (1993).