A8126

Acriflavine

Powder

• Synonym(s): 3,6-Diamino-10-methylacridinium chloride mixt. with 3,6-diaminoacridine (proflavine), Euflavine, Trypaflavine Neutral
• Empirical Formula (Hill Notation): C₁₄H₁₄ClN₃
• CAS Number: 8048-52-0
• Molecular Weight: 259.73
• MDL number: MFCD00064307
• UNSPSC Code: 12171500
• PubChem Substance ID: 24891319
• NACRES: NA.47

Properties

• product name: Acriflavine, fluorescent label
• form: powder
• mp: 179-181 °C
• solubility: H₂O: 0.33 g/mL (lit.)(lit.)
• εmax: ≥48000 at 459-465 nm in methanol at 0.004 g/L; ≥50000 at 259-265 nm in methanol at 0.004 g/L
• application(s): diagnostic assay manufacturing; hematology; histology
• storage temp.: room temp
• SMILES string: [Cl-].Nc1ccc2cc3ccc(N)cc3nc2c1.C[n+]4c5cc(N)ccc5cc6ccc(N)cc46
• InChI: 1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H
• InChI key: PEJLNXHANOHNSU-UHFFFAOYSA-N

Description

Application

Acriflavine is used to fluorescently label high molecular weight RNA molecules .
Excitation and emission wavelengths in various solvents :

• Methanol: λex = 424 nm; λem = 518 nm
• Ethanol: λex = 426 nm; λem = 524 nm
• Propanol: λex = 430 nm; λem = 512 nm
• Butanol: λex = 430 nm; λem = 526 nm
• Formamide: λex = 434 nm; λem = 524 nm
• Glycerol: λex = 432 nm; λem = 540 nm
• Water: λex = 416 nm; λem = 514 nm

Insoluble in ether, chloroform, and fixed oils. Utilized in fluorescence steady state measurements as a donor molecule (when paired with rhodamine 6G as the acceptor) to function as a pH sensor .

• Acriflavine has been used in the agglutination test to distinguish between smooth and rough colony formation of Brucella melitensis.
• It has been used as an Ago2 (argonaute 2) inhibitor.
• It has been used as an inhibitor of HIF-ARNT (hypoxia-inducible factor - aryl hydrocarbon receptor nuclear translocator) complex formation.
• It has been used to study the bacteriocin production by Carnobacterium piscicola.

Biochem/physiol Actions

Acriflavine also interacts with HIF-1α (hypoxia-inducible factor 1 α) and HIF-2α, and thereby suppresses dimer formation of HIF-1 and transcriptional function. It also has negative effect on tumor growth and vascularization. Acriflavine also exhibits trypanocidal, antibacterial and antiviral activities.

Safety Information

• Pictograms: GHS07
• signalword: Warning
• hcodes: H302,H315,H319,H335
• pcodes: P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable