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158550

Sigma-Aldrich

Acridine Orange hemi(zinc chloride) salt

Dye content 85 %

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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
Linear Formula:
C17H20ClN3 · HCl · 1/2ZnCl2
CAS Number:
10127-02-3
Molecular Weight:
369.96
Colour Index Number:
46005
Beilstein:
3734978
EC Number:
233-353-6
MDL number:
MFCD00081043
UNSPSC Code:
12171500
PubChem Substance ID:
24849765
NACRES:
NA.47

form

powder

Quality Level

200

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
GHS08

Signal Word

Warning

Hazard Statements

H341

Hazard Classifications

Muta. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Intracellular chromosome breaks on silicon surface.
Jiang J
Biomaterials, 30(14), 2661-2665 (2009)
An application of Acridine Orange fluorescent staining to the micronucleus test.
Hayashi M
Mutation Research, 120(4), 241-247 (1983)
J F Golden et al.
The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society, 27(1), 522-528 (1979-01-01)
A system for screening cervical cytological preparations is described which employs the Leitz Texture Analyzer System (E. Leitz, Rockleigh, N. J.) quantitative staining with acridine orange, and a fluorescence standard. The instrumentation scans cells on microscope slides and detects objects
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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