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69587

Sigma-Aldrich

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid sodium salt hydrate

BioReagent, suitable for fluorescence, ≥96.5% (HPLC)

Synonyme(s) :

4-MUNANA, 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid sodium salt hydrate, 4-Methylumbelliferyl-N-acetyl-α-D-neuraminic acid sodium salt hydrate

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About This Item

Formule empirique (notation de Hill):
C21H24NNaO11 · xH2O
Numéro CAS:
76204-02-9
Poids moléculaire :
489.41 (anhydrous basis)
Code UNSPSC :
12352106
Nomenclature NACRES :
NA.32

Gamme de produits

BioReagent

Pureté

≥96.5% (HPLC)

Forme

powder

Impuretés

≤0.5% free 4-methylumbelliferone
≤10% water

Solubilité

H2O: 50 mg/mL, clear, very slightly yellow

Fluorescence

λex 315 nm; λem 374 nm (pH.7.0)
λex 365 nm; λem 445 nm (after cleavage by neuraminidase)

Adéquation

suitable for fluorescence

Température de stockage

−20°C

Chaîne SMILES 

O.[H]C(O)(CO)[C@]([H])(O)[C@@H]1OC(C[C@H](O)[C@H]1NC(C)=O)(Oc2ccc3C(C)=CC(=O)Oc3c2)C(=O)O[Na]

InChI

1S/C21H25NO11.Na.H2O/c1-9-5-16(27)31-15-6-11(3-4-12(9)15)32-21(20(29)30)7-13(25)17(22-10(2)24)19(33-21)18(28)14(26)8-23;;/h3-6,13-14,17-19,23,25-26,28H,7-8H2,1-2H3,(H,22,24)(H,29,30);;1H2/q;+1;/p-1/t13-,14?,17+,18?,19+,21+;;/m0../s1

Clé InChI

NSQMRVBWXQQIKF-NVRWCLOTSA-M

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Catégories apparentées

Description générale

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid or 4-MUNANA is a synthetic fluorometric substrate that mimics the naturally occurring neuraminidase enzyme substrate. The enzyme-substrate hydrolysis results in the product 4-methylumbelliferone (4-MU), measured fluorometrically.

Application

2′-(4-Methylumbelliferyl)-α-D-N-acetylneuraminic acid or 4-MUNANA is used as a substrate for the development of a microplate-based assay for neuraminidase inhibitors. The fluorogenic substrate 2ʹ-(4-methylumbelliferyl)-α-D-N-acetylneuraminic acid (4-MUNANA) is used to study the molecular mechanisms of aspirin and celecoxib targeting mammalian neuraminidase-1.

Actions biochimiques/physiologiques

Substrate for fluorometric assay of neuraminidase. Used for fluorescent staining of sialidases in PAGE.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Wei Yang et al.
Carbohydrate research, 359, 92-96 (2012-08-29)
Two novel N-acetylneuraminic acid derivatives, luciferyl N-acetylneuraminic acid (1) and luciferyl 4,7-di-O-methyl-N-acetylneuraminic acid (2), were designed and synthesized as substrates for the rapid detection of influenza virus neuraminidase. The sensitivity and specificity of the assays with compound 1 or 2
Jarinrat Kongkamnerd et al.
Journal of biomolecular screening, 16(7), 755-764 (2011-06-04)
Many assays aimed to test the inhibitory effects of synthetic molecules, and naturally occurring products on the neuraminidase activity exploit the hydrolysis of 2'-O-(4-methylumbelliferyl)-N-acetylneuraminic acid (4-MUNANA). The amount of the released product, 4-methylumbelliferone (4-MU), is then measured fluorimetrically. The authors
Macarena P Quintana-Hayashi et al.
Infection and immunity, 87(7) (2019-04-17)
Infection with Brachyspira hyodysenteriae results in mucoid hemorrhagic diarrhea. This pathogen is associated with the colonic mucus layer, mainly composed of mucins. Infection regulates mucin O-glycosylation in the colon and increases mucin secretion as well as B. hyodysenteriae binding sites
A F Li et al.
Drug discoveries & therapeutics, 3(6), 260-265 (2009-12-01)
Neuraminidase (NA) represents a highly promising new target for drug development in influenza virus genes. Rapid screening of enzyme inhibitors is a key method for the identification of leading compounds. In order to speed up the screening for enzyme inhibitors
Bessi Qorri et al.
Drug design, development and therapy, 14, 4149-4167 (2020-10-30)
Aspirin (acetylsalicylic acid) and celecoxib have been used as potential anti-cancer therapies. Aspirin exerts its therapeutic effect in both cyclooxygenase (COX)-dependent and -independent pathways to reduce tumor growth and disable tumorigenesis. Celecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, reduces factors that
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