10127-02-3
Chemical Structure
Acridine Orange zinc chloride salt
Synonym(s): Euchrysine 3RX
- CAS No.: 10127-02-3
- Formula:C17H20Cl3N3Zn
- Molecular Weight:438.10
InChIKey: VADJQOXWNSPOQA-UHFFFAOYSA-L
SMILES: Cl[Zn]Cl.CN(C)C1=CC=C2C(N=C3C=C(N(C)C)C=CC3=C2)=C1.Cl
Biological Activity: Acridine Orange zinc chloride salt is a cell-permeable fluorescent nucleic acid dye and lysosomal probe with a pKa of 9.65. Acridine Orange zinc chloride salt enters cells via passive diffusion, is protonated and accumulates in acidic lysosomes, and forms aggregates at high concentrations, producing orange-red fluorescence; when the lysosomal proton gradient or membrane integrity is impaired, Acridine Orange zinc chloride salt is released into the cytoplasm, green fluorescence increases and red fluorescence decreases, so it can be used to monitor lysosomal acidification status and changes in membrane permeability. Acridine Orange zinc chloride salt binds to nucleic acids through intercalation or electrostatic interactions, exhibiting mainly green fluorescence when bound to double-stranded DNA and mainly red fluorescence when bound to RNA or single-stranded DNA, and can be used for nucleic acid staining and differential DNA/RNA detection. The Ex/Em of Acridine Orange zinc chloride salt monomer is approximately 492/525 nm; when bound to double-stranded DNA it is approximately 488/520-524 nm, and when bound to RNA or single-stranded DNA it is approximately 457/630-650 nm[1][2][3].
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Acridine Orange zinc chloride salt | Acridine Orange zinc chloride salt is a cell-permeable fluorescent nucleic acid dye and lysosomal probe with a pKa of 9.65. Acridine Orange zinc chloride salt enters cells via passive diffusion, is protonated and accumulates in acidic lysosomes, and forms aggregates at high concentrations, producing orange-red fluorescence; when the lysosomal proton gradient or membrane integrity is impaired, Acridine Orange zinc chloride salt is released into the cytoplasm, green fluorescence increases and red fluorescence decreases, so it can be used to monitor lysosomal acidification status and changes in membrane permeability. Acridine Orange zinc chloride salt binds to nucleic acids through intercalation or electrostatic interactions, exhibiting mainly green fluorescence when bound to double-stranded DNA and mainly red fluorescence when bound to RNA or single-stranded DNA, and can be used for nucleic acid staining and differential DNA/RNA detection. The Ex/Em of Acridine Orange zinc chloride salt monomer is approximately 492/525 nm; when bound to double-stranded DNA it is approximately 488/520-524 nm, and when bound to RNA or single-stranded DNA it is approximately 457/630-650 nm. | |||||||||||||||||||||
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References
- [1]. Eriksson I, et al. Real-Time Monitoring of Lysosomal Membrane Permeabilization Using Acridine Orange. Methods Protoc. 2023 Aug 9;6(4):72. [Content Brief]
- [2]. Darzynkiewicz Z, et al. Differential staining of DNA and RNA. Current protocols in cytometry. 2004 Nov;Chapter 7:Unit 7.3. [Content Brief]
- [3]. Yektaeian N, et al. Lipophilic tracer Dil and fluorescence labeling of acridine orange used for Leishmania major tracing in the fibroblast cells. Heliyon. 2019 Dec 18;5(12):e03073. [Content Brief]