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A8126 Sigma-Aldrich

Acriflavine

Synonym: 3,6-Diamino-10-methylacridinium chloride mixt. with 3,6-diaminoacridine (proflavine), Euflavine, Trypaflavine Neutral

  • CAS Number 8048-52-0

  • Empirical Formula (Hill Notation) C14H14ClN3

  • Molecular Weight 259.73

  •  MDL number MFCD00064307

  •  PubChem Substance ID 24891319

  •  NACRES NA.47

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Properties

Related Categories A, Alphabetical, Biochemicals and Reagents, Cell Biology, Fluorescent Probes, Labels, Particles and Stains,
Quality Level   200
form   powder
application(s)   hematology: suitable
  histology: suitable
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
Featured Industry   Diagnostic Assay Manufacturing
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.

Packaging

25, 100 g in glass bottle

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 & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
WGK 3
RTECS 
AR9660000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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