494-38-2 Usage
Description
ACRIDINE ORANGE is a cell-permeable, nucleic acid-selective fluorescent cationic dye that is useful for cell cycle determination and detection of cellular autophagy. It is a member of the class of aminoacridines, carrying two dimethylamino substituents at positions 3 and 6. The hydrochloride salt of ACRIDINE ORANGE is the fluorescent dye 'acridine orange'. It exhibits excitation/emission spectra of 502/525, 460/650, and 475/590 nm when bound to double-stranded DNA (dsDNA), single-stranded DNA (ssDNA) or RNA, and under acidic conditions, respectively. The ratio of acridine orange emission at 590 to emission at 525 nm can be used to quantify the increase in the number of acidic vesicular organelles observed during cellular autophagy. It is a brilliant yellow-orange compound, soluble in water and ethanol, and exhibits green fluorescence. In concentrated sulfuric acid, it is almost colorless but still shows green fluorescence upon dilution.
Uses
1. Used in Biomedical Research:
ACRIDINE ORANGE is used as a fluorescent nucleic acid binding dye for cell cycle determination and detection of cellular autophagy. It interacts with both DNA and RNA, emitting green fluorescence when bound to DNA (Em=525 nm) and red fluorescence when bound to RNA (Em=~650 nm). This property allows researchers to study the cell cycle and autophagy processes in cells.
2. Used in Microbiology:
In microbiology, ACRIDINE ORANGE is used as a vital stain for the differentiation of live and dead cells, as well as for the detection of bacterial sporulation and fungal infections. The dye can penetrate the cell membrane of living cells and bind to nucleic acids, allowing for the visualization of cellular structures and the assessment of cell viability.
3. Used in Cytogenetics:
ACRIDINE ORANGE is employed as a staining agent in cytogenetic studies, where it is used to visualize chromosomes and other genetic material during cell division. Its fluorescence properties enable researchers to observe the structure and organization of chromosomes, aiding in the identification of chromosomal abnormalities and genetic disorders.
4. Used in Flow Cytometry:
ACRIDINE ORANGE is utilized in flow cytometry as a fluorescent probe for the analysis of cellular DNA and RNA content. The dye's ability to bind to nucleic acids and emit different fluorescence colors depending on the DNA/RNA structure allows for the quantification of nucleic acid content and the assessment of cellular processes such as cell proliferation and apoptosis.
5. Used in Drug Delivery Systems:
ACRIDINE ORANGE can be used in the development of drug delivery systems, particularly for the targeted delivery of therapeutic agents to specific cells or tissues. Its cell-permeable nature and fluorescence properties make it a suitable candidate for the design of novel drug carriers and the monitoring of drug release and uptake in cells.
Preparation
4,4′-Bis(N,N-dimethyl)aminodiphenylmethane?dinitration, the resultant 4-(4-(Dimethylamino)-3-nitrobenzyl)-N,N-dimethyl-2-nitrobenzenamine?reduction, and acid heating will diamino compound cyclization, then will product oxidation and made free base.
Safety Profile
Poison by subcutaneous route.Questionable carcinogen with experimental tumorigenicand carcinogenic data. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.
Purification Methods
The double salt with ZnCl2 (6g) is dissolved in water (200mL) and stirred with four successive portions (12g each) of Dowex-50 ion-exchange resin (K+ form) to remove the zinc. The solution is then concentrated in vacuum to 20mL, and 100mL of ethanol is added to precipitate KCl which is removed. Ether (160mL) is added to the solution from which, on chilling, the dye crystallises as its chloride. It is separated by centrifugation, washed with chilled ethanol and ether, and dried under vacuum, before being recrystallised from ethanol (100mL) by adding ether (50mL), and chilling. Yield 1g. [Pal & Schubert J Am Chem Soc 84 4384 1962]. It was recrystallised twice as the free base from ethanol or methanol/water by dropwise addition of NaOH (less than 0.1M). The precipitate was washed with water and dried under vacuum. It was dissolved in CHCl3 and chromatographed on alumina: the main sharp band was collected, concentrated and cooled to -20o. The precipitate was filtered off, dried in air, then dried for 2hours under vacuum at 70o. [Stone & Bradley J Am Chem Soc 83 3627 1961, Blauer & Linschitz J Phys Chem 66 453 1962, Albert J Chem Soc 244 1947, Beilstein 22 III/IV 5490, 22/11 V 326.]
Standard
Light Fastness
Melting point
Stable
ISO
Poor
Check Digit Verification of cas no
The CAS Registry Mumber 494-38-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,9 and 4 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 494-38:
(5*4)+(4*9)+(3*4)+(2*3)+(1*8)=82
82 % 10 = 2
So 494-38-2 is a valid CAS Registry Number.
InChI:InChI=1/C17H19N3/c1-19(2)16-10-9-15-13(17(16)20(3)4)11-12-7-5-6-8-14(12)18-15/h5-11H,1-4H3
494-38-2Relevant articles and documents
Light-driven release of cucurbit[8]uril from a bivalent cage
De Vink, Pim J.,Van Der Hek, Tim,Brunsveld, Luc
, p. 6726 - 6731 (2021)
Temporal control over supramolecular systems has great potential for the modulation of binding and assembly events, such as providing orthogonal control over protein activity. Especially light controlled triggering provides unique entries for supramolecular systems to interface in a controlled manner with enzymes. Here we report on the light-induced release of cucurbit[8]uril (CB[8]) from a bivalent cage molecule and its subsequent activation of a proteolytic enzyme, caspase-9, that itself is unresponsive to light. Central to the design is the bivalent binding of the cage with high affinity to CB[8], 100-fold stronger than the UV-inactivated products. The affinity switching occurs in the (sub-)micromolar concentration regime, matching the concentration characteristics required for dimerizing and activating caspase-9 by CB[8]. The light-responsive caged CB[8] concept presented offers a novel platform for tuning and application of switchable cucurbiturils and beyond.
Nitrogen anthracene class compound and its synthetic method and application (by machine translation)
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Paragraph 0123-0126, (2018/05/16)
The invention discloses a formula (2) shown in nitrogen anthracene class of compound and its synthetic method, high Iodized salt as reaction raw material, in the inorganic nitrogen reagent, additive, water, alkali, under the action of the metal catalyst, in the 80 - 150 °C conditions, reacts in a solvent 12 - 60 hours to obtain various nitrogen anthracene class compounds. The invention by post method of introducing nitrogen atoms, to avoid the early stage in the reaction of the nitrogen heterocyclic to metal catalyst of the reaction conditions such as not compatibility; in addition, high Iodized salt in the full utilization of the two aryl, shows that the method of the invention atom economy. Prepared by the method of the invention can be further applied [...] compound of the fluorescent indicator acridine orange synthesis. (by machine translation)
ACID BASE REACTIONS BETWEEN ACRIDINE ORANGE AND SUBSTITUTED PHENOLS IN BENZONITRILE. PART I. THERMODYNAMICS OF ASSOCIATION AND IONIC EQUILIBRIA.
Suettinger,Strohbusch
, p. 744 - 750 (2007/10/02)
Proton transfer reactions of the five substituted phenols 3-Cl-4-nitrophenol CNP, 4-nitrophenol NP, 3-methyl-4-nitrophenol MNP, 4-Cl-3,5-dimethylphenol CMP, and 3,5-dimethylphenol DMP with acridine orange, and the formation of hydrogen bonded complexes AHA** minus of the anions A** minus of CNP, NP, and MNP with the respective phenols AH in benzonitrile solution were investigated by means of absorption spectroscopy. The formation enthalpies of the hydrogen bonded anions AHA** minus are much larger than DELTA H//1, so that DELTA H//2 is mainly determined by this association. On the other hand there is no significant difference between DELTA H//2 and DELTA H//3; thus the hydrogen bond formed between a phenol and a complexed anion AHA** minus is very weak. Substituent effects on the acidity of phenols are about twice as large in benzonitrile as in aqueous solution.
