JC-1 Chemical Properties

Melting point:

275–278 ℃

storage temp. 

room temp

solubility 

Soluble in methanol, N,N-dimethyl formamide, dimethyl sulfoxide

form 

crystals

color 

Deep red

Appearance

Solid Powder

ε(extinction coefficient)

≥175000 at 511-517nm in methanol

λmax

514nm

Stability:

Store as supplied desiccated at -20°C for up to 2 years from the date of purchase. Solutions in DMSO or distilled water may be stored at 4°C for up to 1 year. DO NOT FREEZE/THAW SOLUTIONS. Sterilize solutions only by filtration, not by autoclaving

Biological Applications

Detectingmitochondrialmembrane potential,ABCB1,ABCC1,and ABCG2 transporters inhibitors,nucleic acid hybridization,prostate cancer; treating cellular death,Alzheimer’s disease; apoptosis assay; cytotoxicity assay; hematotoxicity

Major Application

Langmuir-Blodgett films; lasing systems; nonlinear optical materials; photographic materials1,

InChI

InChI=1S/C25H27Cl4N4.HI/c1-5-30-20-12-16(26)17(27)13-21(20)31(6-2)24(30)10-9-11-25-32(7-3)22-14-18(28)19(29)15-23(22)33(25)8-4;/h9-15H,5-8H2,1-4H3;1H/q+1;/p-1

InChIKey

FYNNIUVBDKICAX-UHFFFAOYSA-M

SMILES

C12C=C(C(Cl)=CC=1N(/C(=C\C=C\C1=[N+](CC)C3C=C(Cl)C(Cl)=CC=3N1CC)/N2CC)CC)Cl.[I-]

Safety Information

WGK Germany 

3

F 

10-21

Storage Class

11 - Combustible Solids

JC-1 Usage And Synthesis

Description

JC-1 is a membrane-permeable cationic dye that is used to study mitochondrial integrity in the context of cellular apoptosis. It selectively enters mitochondria and changes fluorescence characteristics with alteration in mitochondrial transmembrane potential (ΔΨm). In healthy cells with a high mitochondrial ΔΨm, JC-1 forms complexes known as J-aggregates, which fluoresce red/orange and may be detected using FL2 settings by flow cytometry. A drop in ΔΨm, a very early event in apoptosis, results in JC-1 monomers, which fluoresce green (FL1 settings on flow cytometers). JC-1 may also be used with fluorescent microscopes or plate readers, using excitation at 520-570 nm and emission at 570-610 nm for J-aggregates and excitation at 485 nm and emission at 535 nm for monomers.

Uses

A dual-emission potential-sensitive probe that can be used to measure mitochondrial membrane potential. JC-1 is a green-fluorescent monomer at low membrane potential. At higher potentials, JC-1 forms red-fluorescent "J-aggregates," which exhibit broad exc

Uses

The cyanine dye JC-1 has been used to determine mitochondrial transmembrane potential.

Definition

ChEBI: 1,1',3,3'-tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine iodide is a cyanine dye and an organic iodide salt. It has a role as a fluorochrome. It contains a 1,1',3,3'-tetraethyl-5,5',6,6'-tetrachloroimidacarbocyanine.

Background

JC-1 is a membrane-permeable cyanine dye used to measure mitochondrial membrane potential. JC-1 is a dual-emission, green-fluorescent dye at low membrane potential and forms red-fluorescence at higher membrane potentials. Monomeric JC-1 is the predominant form in cells exhibiting lower mitochondrial membrane potential, while aggregates of JC-1 are found in cells with higher mitochondrial membrane potential. JC-1 can be used to detect cells undergoing apoptosis, with healthy cells exhibiting red-fluorescence and cytoplasmic JC-1 exhibiting green-fluorescence in apoptotic cells. JC-1 is also a substrate of the multidrug transporter P-glycoprotein, an ATP-binding cassette transporter protein associated with development of multidrug resistance. Transport of JC-1 by P-gp from cells can reduce cellular JC-1 levels, creating a false indication of decreased mitochondrial membrane potential.

References

[1] MARTIN REERS  Lan B C  Thomas W Smith. J-aggregate formation of a carbocyanine as a quantitative fluorescent indicator of membrane potential[J]. Biochemistry Biochemistry, 1991, 30 18: 4480-4486. DOI:10.1021/bi00232a015
[2] S T SMILEY. Intracellular heterogeneity in mitochondrial membrane potentials revealed by a J-aggregate-forming lipophilic cation JC-1.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1991, 88 9: 3671-3675. DOI:10.1073/pnas.88.9.3671
[3] F DI LISA. Mitochondrial membrane potential in single living adult rat cardiac myocytes exposed to anoxia or metabolic inhibition.[J]. Journal of Physiology-London, 1995, 486 1: 1-13. DOI:10.1113/jphysiol.1995.sp020786
[4] J MARIO WOLOSIN  Zheng W  Aldo Zamudio. Application of JC1 for non-toxic isolation of cells with MDR transporter activity by flow cytometry.[J]. PLoS ONE, 2017: e0174905. DOI:10.1371/journal.pone.0174905
[5] SHUO WANG. A novel cytoprotective peptide protects mesenchymal stem cells against mitochondrial dysfunction and apoptosis induced by starvation via Nrf2/Sirt3/FoxO3a pathway[J]. Journal of Translational Medicine, 2017, 15 1. DOI:10.1186/s12967-017-1144-5

Excitation / Emission Maximum

485 nm (monomer), 520-570 nm (aggregate)/535 nm (monomer), 570-610 nm (aggregate)

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