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158550

Sigma-Aldrich

Acridine Orange hemi(zinc chloride) salt

Dye content 85 %

Synonym(s):

3,6-Bis(dimethylamino)acridine hydrochloride zinc chloride double salt, 3,6-Bis(dimethylamino)acridinium chloride hemi(zinc chloride salt), Basic Orange 14

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About This Item

Linear Formula:
C17H20ClN3 · HCl · 1/2ZnCl2
CAS Number:
Molecular Weight:
369.96
Colour Index Number:
46005
Beilstein:
3734978
EC Number:
MDL number:
UNSPSC Code:
12171500
PubChem Substance ID:
NACRES:
NA.47

form

powder

Quality Level

composition

Dye content, 85%

solubility

H2O: 1 mg/mL, clear, orange to very deep orange

λmax

489 nm

application(s)

diagnostic assay manufacturing
hematology
histology

storage temp.

room temp

SMILES string

Cl[H].Cl[H].Cl[Zn]Cl.CN(C)c1ccc2cc3ccc(cc3nc2c1)N(C)C.CN(C)c4ccc5cc6ccc(cc6nc5c4)N(C)C

InChI

1S/2C17H19N3.4ClH.Zn/c2*1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14;;;;;/h2*5-11H,1-4H3;4*1H;/q;;;;;;+2/p-2

InChI key

RAHGLSRJKRXOSY-UHFFFAOYSA-L

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Application

Acridine Orange hemi (zinc chloride) salt has been used to stain primary human umbilical vein endothelial cells (HUVEC) and is used in micronucleus tests (MNTs).
Acridine Orange, a cell-permeable metachromatic fluorescent cationic dye that intercalates DNA and RNA, is used in fluorescence and epiflouresence microscopy. Acridine Orange dye has been used to analyze mitochondria and lysosomal content by flow cytometry, characterize multidrug resistance, and measure changes in mitochondrial mass during apoptosis in rat thymocytes.

Biochem/physiol Actions

Acridine orange (AO) is a fluorescent dye with two different staining characteristics. In fixed tissues, it acts as a metachromatic dye and differentially stains DNA (green) and RNA (orange). But, in living cells it acts as a pH indicator and produce brilliant orange-red in acidic condition. AO has been used to identify apoptotic cells in drosophila embryos. Acridine Orange staining method has been used to deliver more consistent data in the micronucleus test.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Muta. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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An application of Acridine Orange fluorescent staining to the micronucleus test.
Hayashi M
Mutation Research, 120(4), 241-247 (1983)
Fluorescence spectroscopic and fading behavior of Ehrlich's hyperdiploid mouse ascites tumor cells supravitally stained with acridine orange.
J F Golden et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 22(7), 495-505 (1974-07-01)
Toxicity of waterborne Copper in premetamorphic tadpoles of Lithobates catesbeianus (Shaw, 1802).
Ossana NA
Bulletin of Environmental Contamination and Toxicology, 84(6), 712-715 (2010)
The problem of pyridinyl imidazole class inhibitors of MAPK14/p38a and MAPK11/p38? in autophagy research.
Menon MB
Autophagy, 11(8), 1425-1427 (2015)
Labilizing action of intercalating drugs and dyes on bacterial ribosomes.
A D Wolfe et al.
Biochemistry, 11(9), 1569-1572 (1972-04-25)

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