Name | Acridine Orange |
Synonyms | Basic Orange 14 Acridine Orange Acridine Orange hemi Acridine OrangeEuchrysin GNY ACRIDINE ORANGE HEMI(ZINC CHLORIDE) ACRIDINE ORANGE ZINC CHLORIDE DOUBLE SAL 3,6-Bis(dimethylamino)acridine zinc chloride hydrochloride Acridine orange zinc chloride double salt (C.I.46005) for microscopy Certistain N,N,N',N'-tetramethylacridine-3,6-diamine monohydrochloride, compound with zinc dichloride |
CAS | 10127-02-3 |
EINECS | 233-353-6 |
InChI | InChI=1/2C17H19N3.4ClH.Zn/c2*1-19(2)14-7-5-12-9-13-6-8-15(20(3)4)11-17(13)18-16(12)10-14;;;;;/h2*5-11H,1-4H3;4*1H;/q;;;;;;+2/p-2 |
Molecular Formula | C17H20Cl3N3Zn |
Molar Mass | 438.1 |
Melting Point | 165 °C |
Water Solubility | soluble |
Solubility | Soluble in water, ethanol is orange-yellow with green fluorescence |
Appearance | Orange red powder |
Color | Red brown |
BRN | 3734978 |
pKa | pKa -3.3(H2O T=room temperature(RT) Iunspeci?ed) (Uncertain);0.2(H2O T=room temperature(RT) Iunspeci |
PH | 3.9 (10g/l, H2O, 20℃) |
Storage Condition | room temp |
Stability | Stable. Incompatible with strong oxidizing agents. Protect from moisture. Hygroscopic. |
Sensitive | Hygroscopic |
MDL | MFCD00081043 |
Use | This product is for scientific research only and shall not be used for other purposes. |
Risk Codes | R68 - Possible risk of irreversible effects R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
RTECS | AR7600000 |
HS Code | 32041300 |
Toxicity | A dye used to stain nucleic acids. It fluoresces at 530 nm when intercalated into double stranded DNA, or at 640 nm when ionically bound to single stranded DNA. It produces mutations, some involving reading frame shifts, other deletions or insertions and is carcinogenic. It is also known to be a dermal phototoxicant. |
Reference Show more | 1. Peng Xue, Li Yunyun, Jin Mengxing, et al. Simvastatin inhibits oxLDL-induced macrophage death [J]. Journal of Anhui Medical University, 2017, 052(011):1654-1658. 2. You Jing, Zhang Wentao, Miao Yanqing, Zhang Xuejiao, Liang Lingling. Study on Drug Loadability and Antitumor Activity of Carboxymethyl Chitosan-Oleic Acid Polymer [J]. Chemistry and bioengineering, 2021,38(01):22-25 33. 3. [IF = 3.439] Wang Hongcheng et al."Gambogic acid induces autophagy and combines synergistically with chloroquine to suppress pancreatic cancer by increasing the accumulation of reactive oxygen species." Cancer Cell Int. 2019 Dec;19(1):1-15 4. [IF = 7.086] Weixiang Wang et al."Developmental toxicity and alteration of gene expression in zebrafish embryo exposed to 6-benzylaminopurine." Chemosphere. 2019 Oct;233:336 5. [IF = 4.33] Le Gu et al."Study on chemical constituents of Folium Artemisiae argyi Carbonisatum, toxicity evaluation on zebrafish and intestinal hemostasis." Saudi Pharm J. 2022 Mar;: 6. [IF = 2.552] Pang Yuesheng et al."Mechanism of berberine hydrochloride interfering with biofilm formation of Hafnia alvei." Arch Microbiol. 2022 Feb;204(2):1-9 |
color index | 46005 |
The structure of acridine orange and its interaction with H or OH- | The AO molecule contains an electron-donating group dimethylamine group, and the nitrogen atom on the ring does not participate in bonding, and is still hybridised with sp2 to form n-π conjugation with the benzene ring. Therefore, the N atom on the acridine ring is prone to quaternary ammonium base reaction. AO interacts with H or OH-, so AO can be seen as a fluorescent dye with conjugated acid-base type. The dissociation of acidic groups or the protonation of basic groups may change the non-radiative transition that competes with the luminescence process. The nature and rate of the process will also change the ability of AO to form hydrogen bonds in aqueous solution, thereby affecting the fluorescence spectrum and intensity of the compound. |
use | forms a green fluorescent complex with double-stranded DNA, and can also form a red fluorescent complex with single-stranded DAN or RNA. A molecule embedded in double-stranded DNA with three base pairs and a maximum wavelength of 526nm (502nm) green fluorescence. A molecule reacts with a phosphate group of single-stranded DNA or RNA to form an aggregated or stacked structure with a maximum wavelength of 650nm (460nm) red fluorescence. Used to detect double-stranded DNA and single-stranded DNARNA. It is possible to simultaneously measure DNARNA with argon laser exciter and flow cytometer as fluorescent indicator, mutagen for tumor cells and bacteria, nucleic acid stain and frameshift mutation. Acridine orange is a fluorescent pigment, acridine orange excitation filter wavelength 488nm. Blocking filter wavelength 515nm. Acridine orange is different from the amount of DNA and RNA binding in cells, and can emit fluorescence of different colors (I. e. coloring specificity). This is because DNA is a highly polymer, and there are fewer places to absorb fluorescent substances and emit green fluorescence. However, the degree of RNA polymerization is low, and there are many places that can combine with fluorescent substances, so red fluorescence is emitted. |