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Acridine orange - Wikipedia, the free encyclopedia

Acridine orange

From Wikipedia, the free encyclopedia

Acridine orange
Acridine orange
IUPAC name N,N,N',N'-tetramethylacridine-
3,6-diamine
Other names Euchrysine
3,6-Acridinediamine
Waxoline Orange A
Acridine Orange Base
Solvent Orange 15
Rhoduline Orange
Rhoduline Orange N
Acridine Orange NO
Rhoduline Orange NO
Basic Orange 14
Identifiers
CAS number [494-38-2]
PubChem 62344
RTECS number AR7601000
SMILES CN(C)C1=CC2=C(C=C1)C=C3C=CC(=CC3=N2)N(C)C
Properties
Molecular formula C17H19N3
Molar mass 265.35
Appearance Orange powder
Hazards
EU classification Irritant Xi Template:Hazchem N
NFPA 704
0
2
0
 
S-phrases S26 S28 S37 S45
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Acridine orange is a nucleic acid selective fluorescent cationic dye useful for cell cycle determination. It is cell-permeable, and interacts with DNA and RNA by intercalation or electrostatic attractions. When bound to DNA, it is very similar spectrally to fluorescein, with an excitation maximum at 502 nm and an emission maximum at 525 nm (green). When it associates with RNA, the excitation maximum shifts to 460 nm (blue) and the emission maximum shifts to 650 nm (red). The dye is often used in epifluorescence microscopy.

Acridine orange is prepared from coal tar and creosote oil.

Acridine orange can be used in conjunction with ethidium bromide to differentiate between live and apoptotic cells.

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