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01673

Sigma-Aldrich

Acriflavine

BioReagent, suitable for fluorescence, ≥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

Quality Level

100

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
[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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335,H400

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - 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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ6459
BCCF5485
BCCB1935
BCBZ9486
BCBZ2004

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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
Carmen Chak-Lui Wong et al.
Journal of molecular medicine (Berlin, Germany), 90(7), 803-815 (2012-01-11)
Intratumoral hypoxia, a frequent finding in metastatic cancer, results in the activation of hypoxia-inducible factors (HIFs). HIFs are implicated in many steps of breast cancer metastasis, including metastatic niche formation through increased expression of lysyl oxidase (LOX) and lysyl oxidase-like
Jun Fang et al.
Journal of biomolecular structure & dynamics, 31(4), 385-392 (2012-08-11)
The resistance-nodulation-cell division family multidrug transporter Acriflavine resistance protein B (AcrB) from Eschericha coli is an obligate homotrimer. Approximately, 45% of the inter-subunit interface is contributed by a protruding loop (also referred to as the thumb) and its corresponding binding
Saadia Hassan et al.
Cancer science, 102(12), 2206-2213 (2011-09-14)
A high-throughput screen of the cytotoxic activity of 2000 molecules from a commercial library in three human colon cancer cell lines and two normal cell types identified the acridine acriflavin to be a colorectal cancer (CRC) active drug. Acriflavine was
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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