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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

Quality Level

100

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

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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Yuqing Chang et al.
Analytical biochemistry, 427(1), 91-98 (2012-05-23)
A quantitative and highly sensitive method for the analysis of glycosaminoglycan (GAG)-derived disaccharides that relies on capillary electrophoresis (CE) with laser-induced fluorescence detection is presented. This method enables complete separation of 17 GAG-derived disaccharides in a single run. Unsaturated disaccharides
Carolyn G Chen et al.
Matrix biology : journal of the International Society for Matrix Biology, 90, 1-19 (2020-02-23)
Hyaluronan plays a key role in regulating inflammation and tumor angiogenesis. Of the three transmembrane hyaluronan synthases, HAS2 is the main pro-angiogenic enzyme responsible for excessive hyaluronan production. We discovered that HAS2 was degraded in vascular endothelial cells via autophagy
Fabio Galeotti et al.
Analytical chemistry, 83(17), 6770-6777 (2011-07-26)
A high-resolution online reverse-phase-high-performance liquid chromatography (RP-HPLC)-fluorescence detector (Fd)-electrospray ionization-mass spectrometry (ESI-MS) separation and structural characterization of disaccharides prepared from heparin (Hep), heparan sulfate (HS), and various low-molecular-weight (LMW)-Hep using heparin lyases and derivatization with 2-aminoacridone (AMAC) are described. A
Wing Lee Chan et al.
PLoS genetics, 14(3), e1007242-e1007242 (2018-03-22)
Gerodermia osteodysplastica (GO) is characterized by skin laxity and early-onset osteoporosis. GORAB, the responsible disease gene, encodes a small Golgi protein of poorly characterized function. To circumvent neonatal lethality of the GorabNull full knockout, Gorab was conditionally inactivated in mesenchymal
Eiki Maeda et al.
Electrophoresis, 27(10), 2002-2010 (2006-04-19)
The conformational separation of monosaccharides labeled with fluorescent 2-aminoacrydone (AMAC) was performed by electrophoresis on a plastic microchip with light-emitting diode confocal fluorescence detection. The AMAC-labeled five neutral monosaccharide mixture (D-glucose (Glc), D-mannose, D-galactose, L-fucose, and D-xylose) or two amino
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Glycan Labeling

Glycans play a key role in protein structure and disease; representation on cell surfaces is the glycome.

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