Available from stock

Acridine Orange base

SKU: A0081

Category: Fluorescent Detection

Synonyms: 3,6-Bis(dimethylamino)acridine, Solvent Orange 15, C.I. 46005B, Brilliant Acridine Orange E, Acridine orange free base, NSC 194350; 494-38-2
CAS-Number: C₁₇H₁₉N₃
Molecular Formula: 265.35
Molecular Weight

For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥75% (HPLC)
Appearance: Orange powder
Identity: 1H-NMR

Properties

Solvents: Soluble in DMSO (20mg/ml). Slightly soluble in water (1mg/ml).
Melting Point: 165 °C (dec.) (lit.)
UV / Vis: λmax 488 nm

Shipping: AMBIENT
Short Term Storage: RT
Long Term Storage: RT
Handling Advice: Protect from light and moisture.
Use / Stability: Stable for at least 2 years after receipt when stored at RT.

Transportation: Not dangerous goods

Description: Acridine Orange Base is a metachromatic fluorescent dye that stains DNA and RNA. It is only slightly soluble compared to its HCL salt form. It is used as a nucleic acid-selective fluorescent cationic dye useful for cell cycle determination and staining dead cells. Being cell-permeable, it interacts with DNA and RNA by intercalation or electrostatic attractions respectively. When bound to DNA, it is very similar spectrally to fluorescein, with an excitation maximum at 502nm and an emission maximum at 525nm (green). When acridine orange associates with RNA or ssDNA, the excitation maximum shifts to 460nm (blue), and the emission maximum shifts to 650nm (red). Acridine orange will also enter acidic compartments such as lysosomes where it becomes protonated and sequestered. At low pH (inside the organelles), it will emit an orange fluorescence (peak at 590nm) and for optimal endosome visualization a blue light excitation (475nm) is used. Thus, acridine orange can be used to visualize primary lysosomes and phagolysosomes that may include products of phagocytosis of apoptotic cells. The dye is often used in epifluorescence microscopy and flow cytometry. It allows for visual detection of nucleic acids on agarose and polyacrylamide gels, can be used for differentiation of dsDNA (green fluorescence) and ssDNA/RNA (red fluorescence) and as a vitality test for determination of living cells. Spectral data: ?Ex=502nm, ?Em=525nm (green, double strands) / ?Ex=460nm, ?Em=650nm (red, single strands) / ?Ex=475nm, ?Em=590nm (orange, acidic conditions).
Smiles: CN(C)C1=CC2=C(C=C1)C=C3C=CC(=CC3=N2)N(C)C
InChi Key: DPKHZNPWBDQZCN-UHFFFAOYSA-N
References: [1] F.H. Kasten, Int. Rev. Cytol. 21, 141 (1967) (Review) , [2] J.F. Golden & S.S. West, J. Histochem. Cytochem. 22, 495 (1974) , [3] J.F. Golden, et al., J. Histochem. Cytochem. 27, 522 (1979) , [4] J.K. Frost, et al., J. Histochem. Cytochem. 27, 545 (1979) , [5] H.W. Tyrer, et al., J. Histochem. Cytochem. 27, 552 (1979) , [6] R.N. Paul, Stain Technol. 55, 195 (1980) , [7] S. Mirrett, Inf. Contr. Hosp. Epidemiol. 3, 250 (1982) (Review) , [8] Z. Darzynkiewicz, et al., Curr. Protoc. Cytom. Chapter 7, Unit 7.3 (2004) (Review) , [9] J. Han & K. Burgess, Chem. Revs. 110, 2709 (2010) , [10] R.W. Sabnis, Handbook of Fluorescent Dyes and Probes (2015) , [11] M.P. Thome, et al., J. Cell Sci. 129, 4622 (2016)

Acridine Orange Base is a metachromatic fluorescent dye that stains DNA and RNA. It is only slightly soluble compared to its HCL salt form. It is used as a nucleic acid-selective fluorescent cationic dye useful for cell cycle determination and staining dead cells. Being cell-permeable, it interacts with DNA and RNA by intercalation or electrostatic attractions respectively. When bound to DNA, it is very similar spectrally to fluorescein, with an excitation maximum at 502nm and an emission maximum at 525nm (green). When acridine orange associates with RNA or ssDNA, the excitation maximum shifts to 460nm (blue), and the emission maximum shifts to 650nm (red). Acridine orange will also enter acidic compartments such as lysosomes where it becomes protonated and sequestered. At low pH (inside the organelles), it will emit an orange fluorescence (peak at 590nm) and for optimal endosome visualization a blue light excitation (475nm) is used. Thus, acridine orange can be used to visualize primary lysosomes and phagolysosomes that may include products of phagocytosis of apoptotic cells. The dye is often used in epifluorescence microscopy and flow cytometry. It allows for visual detection of nucleic acids on agarose and polyacrylamide gels, can be used for differentiation of dsDNA (green fluorescence) and ssDNA/RNA (red fluorescence) and as a vitality test for determination of living cells. Spectral data: ?Ex=502nm, ?Em=525nm (green, double strands) / ?Ex=460nm, ?Em=650nm (red, single strands) / ?Ex=475nm, ?Em=590nm (orange, acidic conditions).

SKU: A0081 Category: Fluorescent Detection

Additional information

Additional information

Synonyms	3,6-Bis(dimethylamino)acridine, Solvent Orange 15, C.I. 46005B, Brilliant Acridine Orange E, Acridine orange free base, NSC 194350
Purity	≥75% (HPLC)
Appearance	Orange powder
CAS-Number	494-38-2
Molecular Formula	C17H19N3
Molecular Weight	265.35
Identity	1H-NMR
Solvents	Soluble in DMSO (20mg/ml). Slightly soluble in water (1mg/ml).
Melting Point	165 °C (dec.) (lit.)
UV / Vis	λmax 488 nm
Smiles	CN(C)C1=CC2=C(C=C1)C=C3C=CC(=CC3=N2)N(C)C
InChi Key	DPKHZNPWBDQZCN-UHFFFAOYSA-N
Shipping	AMBIENT
Short Term Storage	RT
Long Term Storage	RT
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at RT.
Transportation	Not dangerous goods
References	[1] F.H. Kasten, Int. Rev. Cytol. 21, 141 (1967) (Review), [2] J.F. Golden & S.S. West, J. Histochem. Cytochem. 22, 495 (1974), [3] J.F. Golden, et al., J. Histochem. Cytochem. 27, 522 (1979), [4] J.K. Frost, et al., J. Histochem. Cytochem. 27, 545 (1979), [5] H.W. Tyrer, et al., J. Histochem. Cytochem. 27, 552 (1979), [6] R.N. Paul, Stain Technol. 55, 195 (1980), [7] S. Mirrett, Inf. Contr. Hosp. Epidemiol. 3, 250 (1982) (Review), [8] Z. Darzynkiewicz, et al., Curr. Protoc. Cytom. Chapter 7, Unit 7.3 (2004) (Review), [9] J. Han & K. Burgess, Chem. Revs. 110, 2709 (2010), [10] R.W. Sabnis, Handbook of Fluorescent Dyes and Probes (2015), [11] M.P. Thome, et al., J. Cell Sci. 129, 4622 (2016)
Quantity	25 g, Bulk