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01673

Sigma-Aldrich

Acriflavine

suitable for fluorescence, BioReagent, ≥90% (AT)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C14H14ClN3
CAS Number:
8048-52-0
Molecular Weight:
259.73
MDL number:
MFCD00064307
UNSPSC Code:
12171500
PubChem Substance ID:
329747342
NACRES:
NA.32

product line

BioReagent

assay

≥90% (AT)

form

powder

composition

Sum of components 3,6-diaminoacridinium chloride and 3,6-diamino-10-methylacridinium chloride, ≥70% HPLC

solubility

H2O: 0.33 g/mL (lit.)(lit.)

fluorescence

λex 463 nm; λem 490 nm in ethanol

suitability

suitable for fluorescence

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 .

Other Notes

DNA fluorochrome. Application in dual fluorescence analysis of cellular DNA and protein simultaneously

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - 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

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
M Stöhr et al.
Stain technology, 53(4), 205-215 (1978-07-01)
Eight fluorescent dye combinations for simultaneous DNA-protein staining have been evaluated spectroscopically and flow microfluorometrically: propidium iodide (PI) with fluoresceinisothiocyanate (FITC), fluorescamine (FC), and dansylchloride (DANS); diamidinophenylindole (DAPII) with sulphorhodamin (SR101), tetramethylrhodamin isothiocyanate (TRITC), and nitrobenzodiazole (NBD); acriflavine (AF) with
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.
Ivan Gusarov et al.
Science (New York, N.Y.), 325(5946), 1380-1384 (2009-09-12)
Bacterial nitric oxide synthases (bNOS) are present in many Gram-positive species and have been demonstrated to synthesize NO from arginine in vitro and in vivo. However, the physiological role of bNOS remains largely unknown. We show that NO generated by
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