DiOC6

DiOC6^[1]
Names
	IUPAC name 3-Hexyl-2-[3-(3-hexyl-2(3H)benzoxazolylidene)-1-propenyl]benzoxazolium iodide
	Other names 3,3′-Dihexyloxacarbocyanine iodide
Identifiers
CAS Number	53213-82-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	93680 ;
ECHA InfoCard	100.155.178
PubChem CID	9894321;
UNII	NL6XJC6U28 ;
CompTox Dashboard (EPA)	DTXSID00886043 ;
	InChI InChI=1S/C29H37N2O2.HI/c1-3-5-7-13-22-30-24-16-9-11-18-26(24)32-28(30)20-15-21-29-31(23-14-8-6-4-2)25-17-10-12-19-27(25)33-29;/h9-12,15-21H,3-8,13-14,22-23H2,1-2H3;1H/q+1;/p-1 Key: XVLXYDXJEKLXHN-UHFFFAOYSA-M ; InChI=1/C29H37N2O2.HI/c1-3-5-7-13-22-30-24-16-9-11-18-26(24)32-28(30)20-15-21-29-31(23-14-8-6-4-2)25-17-10-12-19-27(25)33-29;/h9-12,15-21H,3-8,13-14,22-23H2,1-2H3;1H/q+1;/p-1 Key: XVLXYDXJEKLXHN-REWHXWOFAI;
	SMILES [I-].o1c4ccccc4[n+](c1C=CC=C3Oc2ccccc2N3CCCCCC)CCCCCC;
Properties
Chemical formula	C29H37IN2O2
Molar mass	572.531 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

DiOC₆ (3,3′-dihexyloxacarbocyanine iodide) is a fluorescent dye used for the staining of a cell's endoplasmic reticulum,^[2] vesicle membranes and mitochondria.^[3] Binding to these structures occurs via the dye's hydrophilic groups. DiOC₆ can be used to label living cells, however they are quickly damaged due to the dye's extreme phototoxicity, so cells stained with this dye can only be exposed to light for short periods of time. When exposed to blue light, the dye fluoresces green.

References

^ 3,3′-Dihexyloxacarbocyanine iodide at Sigma-Aldrich
^ Terasaki M. (1989). "Fluorescent labeling of endoplasmic reticulum". Methods Cell Biol. 29: 125–35. doi:10.1016/s0091-679x(08)60191-0. PMID 2643757.
^ Koning AJ; et al. (1993). "DiOC6 staining reveals organelle structure and dynamics in living yeast cells". Cell Motil Cytoskeleton. 25 (2): 111–28. doi:10.1002/cm.970250202. PMID 7686821.

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[1] 3,3′-Dihexyloxacarbocyanine iodide at Sigma-Aldrich

[2] Terasaki M. (1989). "Fluorescent labeling of endoplasmic reticulum". Methods Cell Biol. 29: 125–35. doi:10.1016/s0091-679x(08)60191-0. PMID 2643757.

[3] Koning AJ; et al. (1993). "DiOC6 staining reveals organelle structure and dynamics in living yeast cells". Cell Motil Cytoskeleton. 25 (2): 111–28. doi:10.1002/cm.970250202. PMID 7686821.

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See also

References