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06627

Sigma-Aldrich

2-Aminoacridone

BioReagent, suitable for fluorescence, ≥98.0% (HPLC)

Synonym(s):

2-Amino-9(10H)-acridinone, 2-amino-10H-acridin-9-one, AMAC

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About This Item

Empirical Formula (Hill Notation):
C13H10N2O
CAS Number:
27918-14-5
Molecular Weight:
210.23
Beilstein:
172520
MDL number:
MFCD00037397
UNSPSC Code:
12352108
PubChem Substance ID:
329748253
NACRES:
NA.32

product line

BioReagent

Assay

≥98.0% (HPLC)

solubility

DMF: soluble
DMSO: soluble

fluorescence

λex 420 nm; λem 542 nm in 0.1 M Tris pH 8.0

suitability

suitable for fluorescence

SMILES string

Nc1ccc2Nc3ccccc3C(=O)c2c1

InChI

1S/C13H10N2O/c14-8-5-6-12-10(7-8)13(16)9-3-1-2-4-11(9)15-12/h1-7H,14H2,(H,15,16)

InChI key

PIGCSKVALLVWKU-UHFFFAOYSA-N

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Application

2-Aminoacridone is a highly fluorescent aromatic, which contains a primary amine group that reacts with an aldehyde group at the reducing end of a carbohydrate and is reduced to a stable amine derivative by sodium borohydride (NaBH4). Picomolar levels of glycan compounds can be detected using this fluorophore. The resulting derivatzed compounds can be separated by reverse-phase HPLC and detected by positive-ion electrospray MS . An intense fluorescent, hydrophobic probe that is stable over a wide pH range is useful in the derivatization of glycans to allow for the analysis of complex oligosaccharides using micellar electrokinetic capillary chromatography and reverse- and normal-phase chromatography coupled with mass spectroscopy to determine relative concentrations and structural identity of individual oligosaccharides . The λ excitation and λ emission are 425 nm and 532 nm, respectively.
Fluorescent label for glycans and saccharides.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Certificates of Analysis (COA)

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Tina Rise Tuveng et al.
PloS one, 12(11), e0187544-e0187544 (2017-11-07)
Chitin, a polymer of β(1-4)-linked N-acetylglucosamine found in e.g. arthropods, is a valuable resource that may be used to produce chitosan and chitooligosaccharides, two compounds with considerable industrial and biomedical potential. Deacetylating enzymes may be used to tailor the properties
Maria Militsopoulou et al.
Electrophoresis, 23(7-8), 1104-1109 (2002-05-01)
In quest for high sensitivities, we developed an ultrahigh capillary electrophoresis (CE) method for the structural analysis of heparin and heparan sulfate (HS) in biologic samples. Heparin and HS were digested with an equi-unit mixture of heparin lyases I, II
Nicola Volpi
Analytical biochemistry, 397(1), 12-23 (2009-09-23)
In this study, we developed an on-line reverse-phase high-performance liquid chromatography-electrospray ionization-mass spectrometry (RP-HPLC-ESI-MS) separation and structural characterization of hyaluronan (HA)/chondroitin sulfate (CS)/dermatan sulfate (DS) disaccharides released by enzymatic treatment and derivatized with 2-aminoacridone (AMAC), providing a high-resolution system also
Martin Giera et al.
The Analyst, 136(13), 2763-2769 (2011-05-26)
Malondialdehyde (MDA) has become a well-established biomarker for oxidative stress. The most commonly used way to determine urinary MDA levels is the thiobarbituric acid (TBA) assay, which suffers from several drawbacks. In this manuscript, we describe a novel derivatization strategy
Yong Zhang et al.
Electrophoresis, 28(3), 414-421 (2007-03-16)
To improve the separation of monosulfate glycosaminoglycan disaccharide isomers by microchip electrophoresis, we found that addition of 1,4-dioxane (DO) dramatically improved analyte resolution, probably due to solvation effects. Methylcellulose (MC) was tested for the ability to suppress EOF and analyte
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Articles

Glycan Labeling

Structural modifications of proteins are essential to living cells. When aberrantly regulated they are often the basis of disease. Glycans are responsible for much of the structural variation in biologic systems, and their representation on cell surfaces is commonly called the “glycome.”

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