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A8126

Sigma-Aldrich

Acriflavine

fluorescent label

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

Quality Level

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

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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.

pictograms

Exclamation mark

signalword

Warning

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


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