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Merck

A8126

Sigma-Aldrich

Acriflavine

Powder

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C14H14ClN3
Número de CAS:
Peso molecular:
259.73
Número MDL:
Código UNSPSC:
12171500
ID de la sustancia en PubChem:
NACRES:
NA.47

Nombre del producto

Acriflavine, fluorescent label

Nivel de calidad

Formulario

powder

técnicas

microbe id | staining: suitable

mp

179-181 °C

solubilidad

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

aplicaciones

diagnostic assay manufacturing
hematology
histology

temp. de almacenamiento

room temp

cadena SMILES

[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

Clave InChI

PEJLNXHANOHNSU-UHFFFAOYSA-N

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Aplicación

  • 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.
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 .

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Visite la Librería de documentos

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
Jessica E S Shay et al.
Carcinogenesis, 35(5), 1067-1077 (2014-01-11)
Hypoxia-inducible factors (HIFs) accumulate in both neoplastic and inflammatory cells within the tumor microenvironment and impact the progression of a variety of diseases, including colorectal cancer. Pharmacological HIF inhibition represents a novel therapeutic strategy for cancer treatment. We show here
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

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