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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:
8048-52-0
Molecular Weight:
259.73
MDL number:
MFCD00064307
PubChem Substance ID:
24891319
NACRES:
NA.47

Quality Level

200

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
GHS07

Signal Word

Warning

Hazard Statements

H302 - H315 - H319 - H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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The contribution of bacteriocin to inhibition of Listeria monocytogenes by Carnobacterium piscicola strains in cold-smoked salmon systems.
Nilsson L, et al.
Journal of Applied Microbiology, 96, 133-133 (2004)
Isolation and biotyping of Brucella melitensis from aborted sheep and goat fetuses.
Buyukcangaz E, et al.
Turkish Journal of Veterinary and Animal Sciences, 33, 311-316 (2009)
Zheqing Cai et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(43), 17462-17467 (2013-10-09)
Both preclinical and clinical studies suggest that brief cycles of ischemia and reperfusion in the arm or leg may protect the heart against injury following prolonged coronary artery occlusion and reperfusion, a phenomenon known as remote ischemic preconditioning. Recent studies
Shizuka Nakayama et al.
Chemical communications (Cambridge, England), 47(16), 4766-4768 (2011-03-15)
The ubiquitous bacterial biofilm regulator, c-di-GMP can form G-quadruplexes at physiological conditions in the presence of some aromatic compounds, such as acriflavine and proflavine. The fluorescence of these compounds is quenched upon c-di-GMP binding and some of the formed c-di-GMP
C E Zubieta et al.
Journal of environmental management, 101, 1-6 (2012-03-06)
The adsorption and photodegradation of acridine orange (AO) and acriflavine (AF) dyes on two mesoporous titania crystalline phases, anatase and rutile, were experimentally studied. Anatase and rutile were characterized by nitrogen adsorption, electron scanning and transmission microscopy, and X-ray diffraction.
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