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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)

Synonym(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

Empirical Formula (Hill Notation):
C21H24NNaO11 · xH2O
CAS Number:
76204-02-9
Molecular Weight:
489.41 (anhydrous basis)
UNSPSC Code:
12352106
NACRES:
NA.32

product line

BioReagent

Assay

≥96.5% (HPLC)

form

powder

impurities

≤0.5% free 4-methylumbelliferone
≤10% water

solubility

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)

suitability

suitable for fluorescence

storage temp.

−20°C

SMILES string

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

InChI key

NSQMRVBWXQQIKF-NVRWCLOTSA-M

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General description

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.

Biochem/physiol Actions

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

69587-5MG:
69587-25MG:
69587-VAR:
69587-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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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