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Acriflavine (Standard)

CAT: 0804-HY-100575RSize: 1 EachDry Ice: NoHazardous: No
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Description
Acriflavine (Standard) is the analytical standard of Acriflavine. This product is intended for research and analytical applications. Acriflavine (Acriflavinium chloride) is a fluorescent acridine dye that can be used to label nucleic acid. Acriflavine is an antiseptic agent. Acriflavine is a potent HIF-1 inhibitor that prevents the dimerization of HIF-1α and HIF-1β subunits. Acriflavine inhibits the interaction between monocarboxylate transporter 4 (MCT4) and Basigin. Acriflavine is used in cancer research, such as breast cancer, brain tumor and chronic myeloid leukemia. Acriflavine is a potent papain-like protease (PLpro) inhibitor, which inhibits SARS-CoV-2[1][2][3][4][5][6].
CAS Number
8048-52-0
Target
Bacterial; Fluorescent Dye; Fungal; HIF/HIF Prolyl-Hydroxylase; Monocarboxylate Transporter; Reference Standards; SARS-CoV
Related Pathways
Anti-infection; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; Others
Field of Research
Cancer; Infection
Smiles
NC(C=C1)=CC(C1=C2)=NC3=C2C=CC(N)=C3.NC(C=C4)=CC(C4=C5)=[N+](C)C6=C5C=CC(N)=C6.[Cl-]
Molecular Formula
C14H14ClN3
Molecular Weight
259.73
References & Citations
[1]Chan LM, et al. Interaction of acriflavine with DNA and RNA. J Mol Biol. 1969 Mar 28;40 (3) :491-5.|[2]Thomas Meinelt, et al. Effects of Calcium Content and Humic Substances on the Toxicity of Acriflavine to Juvenile Zebrafish Danio rerio. Journal of Aquatic Animal Health, 14:1, 35-38.|[3]Voss DM, et al. Disruption of the monocarboxylate transporter-4-basigin interaction inhibits the hypoxic response, proliferation, and tumor progression. Sci Rep. 2017 Jun 27;7 (1) :4292.|[4]Yin T, et al. HIF-1 Dimerization Inhibitor Acriflavine Enhances Antitumor Activity of Sunitinib in Breast Cancer Model. Oncol Res. 2014;22 (3) :139-45.|[5]Cheloni G, et al. Targeting chronic myeloid leukemia stem cells with the hypoxia-inducible factor inhibitor acriflavine. Blood. 2017 Aug 3;130 (5) :655-665.|[6]Napolitano V, et al. Acriflavine, a clinically approved drug, inhibits SARS-CoV-2 and other betacoronaviruses. Cell Chem Biol. 2022 May 19;29 (5) :774-784.e8.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Acriflavine

3,6-Diamino-10-methylacridinium chloride mixt. with 3,6-acridinediamine. Fluorescent dye used as a local antiseptic and also as a biological stain. It intercalates into nucleic acids thereby inhibiting bacterial and viral replication.

CAS Number8048-52-0
PubChem CID443101
IUPAC Nameacridine-3,6-diamine;10-methylacridin-10-ium-3,6-diamine;chloride
Molecular FormulaC27H25ClN6
Molecular Weight469.0
Topological Polar Surface Area121
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Heavy Atom Count34
Formal Charge0
Complexity486
SMILES
C[N+]1=C2C=C(C=CC2=CC3=C1C=C(C=C3)N)N.C1=CC(=CC2=NC3=C(C=CC(=C3)N)C=C21)N.[Cl-]
InChI
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
InChIKey
PEJLNXHANOHNSU-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Acriflavine
CAS: 8048-52-0
CID: 443101
Formula: C27H25ClN6
MW: 469.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight469.0
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Exact Mass468.1829225
Monoisotopic Mass468.1829225
Topological Polar Surface Area121 Ų
Heavy Atom Count34
Formal Charge0
Complexity486
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

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