65-61-2 Usage
Description
ACRIDINE ORANGE is a cationic dye that is known for its interaction with DNA and RNA through intercalation or electrostatic attraction. It is characterized by its bright yellow-orange color and is soluble in water and ethanol, exhibiting green fluorescence. ACRIDINE ORANGE is also known to have a strong sulfuric acid form that is nearly colorless with green fluorescence, and when mixed with strong sodium hydroxide solution, it forms a yellow precipitate. It shares the same chemical structure as C.I. Solvent Orange 15 (free base) and is available as a dark orange to brown powder.
Uses
Used in Molecular Biology and Genetics:
ACRIDINE ORANGE is used as a fluorescent stain for nucleic acids in agarose and polyacrylamide gels. This application is particularly useful in the fields of molecular biology and genetics, where the dye aids in the visualization and analysis of DNA and RNA samples.
Used in Textile Industry (Standard Silk):
In the textile industry, specifically for standard silk, ACRIDINE ORANGE is utilized as a dye. It has been assessed for various fastness properties, including light fastness (ISO 1-2), perspiration fastness (ISO 3), ironing fastness (ISO 1), and soaping (ISO 5). The dye also exhibits fading and staining properties, which are important considerations in the textile manufacturing process.
Preparation
4,4 ‘-Bis (N, N-dimethyl) aminodiphenylmethane obtained dinitration of 4,4′ – bis (N, N-dimethyl) amino-2 ‘- dinitro-diphenyl methane reduction, and with an acid of heat, so that the diamino compound is cyclized product is oxidized and then cyclized and converted into zinc chloride double salt.
Biological Activity
acridine orange hydrochloride is a cell and organelle membrane permeable fluorescent dye that targets nucleic acids. acridine orange can either be incorporated into double helical nucleic acids (detected by green fluorescence at 530 nm), or bind electrostatically to phosphate groups of single-stranded molecules (detected by red fluorescence at 640 nm), which renders it the ability to differently stain dna and rna or single-stranded dna in situ. for unfixed cells, acridine orange staining can still be used as a simple, fast approach of obtaining information on cell cycle status and cell ploidy levels from dna staining (green fluorescence), as well as cell transcriptional activity from rna measurements (red fluorescence), in a flow cytofluorometric system. thus, acridine orange may serve as a useful cytochemical stain for cell-cycle and apoptosis studies.1. mcmaster gk, carmichael gg. analysis of single- and double-stranded nucleic acids on polyacrylamide and agarose gels by using glyoxal and acridine orange. proceedings of the national academy of sciences of the united states of america, 1977, 74(11): 4835-4838.2. traganos f, darzynkiewicz z, sharpless t, et al. simultaneous staining of ribonucleic and deoxyribonucleic acids in unfixed cells using acridine orange in a flow cytofluorometric system. journal of histochemistry and cytochemistry, 1977, 25(1): 46-56.
Safety Profile
Mutation data reported. Whenheated to decomposition it emits very toxic fumes of HCl,Cl??, and NOx.
Enzyme inhibitor
This cell-permeable dye (FWfree-base = 265.36 g/mol; CAS 65-61-2), also known as N,N,N',N'-tetramethylacridine-3,6-diamine, is an intercalator that binds tightly to nucleic acids. Binding to DNA is characterized by excitation maximum at 502 nm (cyan) and an emission maximum at 525 nm, producing a green fluorescence. (A 120 μM solution of acridine orange will detect 25-50 ng DNA per band in an agarose or polyacrylamide gel.) Binding to RNA is characterized by an excitation maximum at 460 nm and the emission maximum is located at 650 nm, yielding a reddish-orange fluorescence. Acridine orange also penetrates acidic compartments (e.g., lysosomes and phagolysosomes); upon protonation, the dye emits orange light when excited by blue light.
Standard( Silk )
Light Fastness
Fading
Stain
ISO
1-2
Check Digit Verification of cas no
The CAS Registry Mumber 65-61-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 5 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 65-61:
(4*6)+(3*5)+(2*6)+(1*1)=52
52 % 10 = 2
So 65-61-2 is a valid CAS Registry Number.
65-61-2Relevant articles and documents
Photo-induced proton-coupled electron transfer reactions of acridine orange: Comprehensive spectral and kinetics analysis
Eisenhart, Thomas T.,Dempsey, Jillian L.
supporting information, p. 12221 - 12224 (2014/11/08)
The triplet excited state of acridine orange (3*AO) undergoes a proton-coupled electron transfer (PCET) reaction with tri-tert-butylphenol (ttbPhOH) in acetonitrile. Each of the reaction components possesses a spectroscopic signature, providing a rare opportunity to monitor the individual proton transfer, electron transfer, and H ?-transfer components in parallel via transient absorption spectroscopy. This enhanced optical tracking, along with excited-state thermochemical analysis, facilitates assignment of the mechanism of excited-state PCET reactivity. 3*AO is quenched via concerted proton-electron transfer (CPET) from ttbPhOH to form acridine radical (AOH?) and ttbPhO? (kCPET = 3.7 × 108 M-1 s-1, KIE = 1.3). Subsequently, AOH? reduces the phenoxyl radical (kET = 5.5 × 109 M-1 s-1), forming AOH + and ttbPhO-, followed by proton transfer (kPT = 1.0 × 109 M-1 s-1) to regenerate the starting reactants.
