Back أكريدين أورانج Arabic Акридин оранж Bulgarian Acridinorange German Akridina oranĝo Esperanto Naranja de acridina Spanish Akridina laranja Basque Akridiinioranssi Finnish Akridinska naranča Croatian Arancio di acridina Italian アクリジンオレンジ Japanese

Acridine orange

Acridine orange
Acridine orange
Acridine orange
Ball-and-stick model of the acridine orange freebase molecule
Names
Preferred IUPAC name
N,N,N′,N′-Tetramethylacridine-3,6-diamine
Systematic IUPAC name
3-N,3-N,6-N,6-N-Tetramethylacridine-3,6-diamine
Other names
3,6-Acridinediamine

Acridine Orange Base
Acridine Orange NO
Basic Orange 14
Euchrysine
Rhoduline Orange
Rhoduline Orange N
Rhoduline Orange NO
Solvent Orange 15

Waxoline Orange A
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.122.153 Edit this at Wikidata
EC Number
  • 200-614-0
KEGG
MeSH Acridine+orange
RTECS number
  • AR7601000
UNII
  • InChI=1S/C17H19N3/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14/h5-11H,1-4H3 checkY
    Key: DPKHZNPWBDQZCN-UHFFFAOYSA-N checkY
  • InChI=1/C17H19N3/c1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14/h5-11H,1-4H3
    Key: DPKHZNPWBDQZCN-UHFFFAOYAJ
  • n1c3c(cc2c1cc(N(C)C)cc2)ccc(c3)N(C)C
Properties
C17H19N3
Molar mass 265.360 g·mol−1
Appearance Orange powder
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation mark
Warning
H302, H312, H341
P281, P304+P340
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Acridine orange is an organic compound that serves as a nucleic acid-selective fluorescent dye with cationic properties useful for cell cycle determination. Acridine orange is cell-permeable, which allows it to interact with DNA by intercalation, or RNA via electrostatic attractions. When bound to DNA, acridine orange is very similar spectrally to an organic compound known as fluorescein.

Acridine orange is used in epifluorescence microscopy and flow cytometry. The ability to penetrate the cell membranes of acidic organelles and cationic properties of acridine orange allows it to differentiate between various types of cells (i.e., bacterial cells and white blood cells).

Acridine orange and fluorescein have a maximum excitation at 502nm and 525 nm (green). When acridine orange associates with RNA, the fluorescent dye experiences a maximum excitation shift from 525 nm (green) to 460 nm (blue). The shift in maximum excitation also produces a maximum emission of 650 nm (red). Acridine orange is able to withstand low pH environments, allowing the fluorescent dye to penetrate acidic organelles such as lysosomes and phagolysosomes that are membrane-bound organelles essential for acid hydrolysis or for producing products of phagocytosis of apoptotic cells. The shift in maximum excitation and emission wavelengths provides a foundation to predict the wavelength at which the cells will stain.[1]

  1. ^ Yektaeian, Narjes; Mehrabani, Davood; Sepaskhah, Mozhdeh; Zare, Shahrokh; Jamhiri, Iman; Hatam, Gholamreza (December 2019). "Lipophilic tracer Dil and fluorescence labeling of acridine orange used for Leishmania major tracing in the fibroblast cells". Heliyon. 5 (12): e03073. Bibcode:2019Heliy...503073Y. doi:10.1016/j.heliyon.2019.e03073. PMC 6928280. PMID 31890980.
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