Nitrocefin

ChemicalBook > CAS DataBase List > Nitrocefin

Product Name: Nitrocefin
CAS No.: 41906-86-9
Chemical Name: Nitrocefin
Synonyms: 3-[(E)-2-(2,4-Dinitrophenyl)vinyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;NITROCEFIN;Nitrocefin (>Nitrocefin (>90%);Cefnitrothiophene;Nitrocefin, Chromogenic cephalosporin beta-lactamase substrate;3-(2,4-DINITROSTYRYL)-(6R, 7R)-7-(2-THIENYLACETAMIDO)-CEPH-3-EM-4 CARBOXYLIC ACID, E-ISOMER;(6R,7R)-7-[[(E)-4-(2,4-Dinitrophenyl)-2-(2-thienyl)but-3-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6R)-3-[(E)-2-(2,4-Dinitrophenyl)ethenyl]-8-oxo-7α-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7R)-
CBNumber: CB1322600
Molecular Formula: C21H16N4O8S2
Formula Weight: 516.5
MOL File: 41906-86-9.mol

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Nitrocefin Property

Melting point:: 103-113° (dec); mp 167-169° (dec) (Lee)
alpha: D20 -224° (c = 1.0 in dioxane)
Boiling point:: 872.0±65.0 °C(Predicted)
Density: 1.67±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:20): 0.04 mg/ml
form: A crystalline solid
pka: 2.50±0.50(Predicted)
color: Yellow to orange
Stability:: Hygroscopic, Unstable in Solution
InChIKey: LHNIIDJCEODSHA-OQRUQETBSA-N
SMILES: N12[C@@]([H])([C@H](NC(CC3SC=CC=3)=O)C1=O)SCC(/C=C/C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O)=C2C(O)=O

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Safety

HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H228Flammable solid

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 484400
Product name: Nitrocefin - CAS 41906-86-9 - Calbiochem
Purity: A chromogenic β-lactamase substrate that undergoes distinctive color change from yellow as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase.
Packaging: 5MG
Price: $177
Updated: 2023/01/07

Cayman Chemical

Product number: 15424
Product name: Nitrocefin
Purity: ≥95%
Packaging: 1mg
Price: $85
Updated: 2024/03/01

Cayman Chemical

Product number: 15424
Product name: Nitrocefin
Purity: ≥95%
Packaging: 5mg
Price: $148
Updated: 2024/03/01

Cayman Chemical

Product number: 15424
Product name: Nitrocefin
Purity: ≥95%
Packaging: 10mg
Price: $253
Updated: 2024/03/01

Cayman Chemical

Product number: 15424
Product name: Nitrocefin
Purity: ≥95%
Packaging: 25mg
Price: $527
Updated: 2024/03/01

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Nitrocefin Chemical Properties,Usage,Production

Description

The generation of β-lactamases by bacteria affords resistance to several classes of β-lactam antibiotics, including penicillins and cephalosporins. Nitrocefin is a chromogenic cephalosporin substrate commonly used to detect β-lactamases in bacteria. The presence of β-lactamase activity is indicated by the appearance of a red color that is proportional in intensity to the original concentration of nitrocefin.

Chemical Properties

Nitrocefin is the chromogenic cephalosporin that acts as an excellent β-lactamase substrate. It exhibits a rapid distinctive color change from yellow (max at pH 7.0 = 390 nm) to red (max at pH 7.0 = 486 nm) as the amide bond in the beta-lactam ring is hydrolyzed by a β-lactamase. It is sensitive to hydrolysis by all known lactamases produced by Gram-positive and Gram-negative bacteria.
Nitrocefin (Yellow) --β-lactamase-->Product (Red) (OD486nm)
Solution preparation and color change before and after β-lactamase exposure

(A) Concentrated nitrocefin (10.0 mg/mL) in DMSO before dilution with PBS buffer. (B) Nitrocefin diluted with PBS buffer to working concentration (1.0 mg/mL). The yellow color is indicative of intact, undegraded nitrocefin. (C) 25 units of betalactamase dropped on top of nitrocefin (1.0 mg/mL in PBS). The red color is the result of beta-lactamase mediated cleavage of the nitrocefin. (D) Vortexed mixture of contents shown in picture (C).

Uses

Nitrocefin is a chromogenic β-lactamase substrate that undergoes colour change from yellow to red as the amide bond in the β-Lactam ring is hydrolyzed by β-lactamase. Nitrocefin undergoes colour chang es induced by lactamases produced by Gram-positive and Gram-negative bacteria. Several studies have utilized the colour changing properties of Nitrocefin for the detection of β-lactamase activity from bacterial cell extracts by isoelectric focusing and spectroscopy. Nitrocefin has also been used in studies involving β-lactamase resistant antibiotics.

Preparation

Nitrocefin is a key reagent for high and low throughput assays of the activities of penicillin-binding proteins (PBPs) and β-lactamases, the former used for discovery of antibiotics and the latter for inhibitors of resistance determinants for β-lactam antibiotics. This compound is commercially available but is prohibitively expensive because of the circuitous routes to its synthesis. We describe herein a three-step synthesis of nitrocefin that gives an overall yield of 44%. This is a practical route to the synthesis of this key reagent for drug discovery.
A Practical Synthesis of Nitrocefin

Biological Functions

In determination of b-lactamase activity in biological samples.
Nitrocefin is a colorless or faint yellow cephalosporin antimicrobial that is hydrolyzed rapidly by most beta-lactamases.The hydrolysis product is pink.The bacterium to be tested is applied to a paper disk containing nitrocefin. A pink color developing within minutes (positive test) indicates a beta-lactamaseproducing bacterium.

Nitrocefin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Nitrocefin manufacturers

Changsha YuTeng New Materials Co., Ltd.

Product: Nitrocefin 41906-86-9
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 90%
Supply Ability: 100g
Release date: 2024-10-15

AFINE CHEMICALS LIMITED

Product: NITROCEFIN 41906-86-9
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: NA
Supply Ability: 5000kgs
Release date: 2023-06-29

Hebei Zhanyao Biotechnology Co. Ltd

Product: NITROCEFIN 41906-86-9
Price: US $10.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 99%
Supply Ability: 20 Tons
Release date: 2021-11-23

41906-86-9, NitrocefinRelated Search:

Berberine Cefotiam hydrochloride Ceftazidime Spiramycin NITROCEFIN DISKS* (2-ISOBUTYRYLAMINO-ACETYLAMINO)-ACETIC ACID Nitrocefin

3-(2,4-DINITROSTYRYL)-(6R, 7R)-7-(2-THIENYLACETAMIDO)-CEPH-3-EM-4 CARBOXYLIC ACID, E-ISOMER

(6R)-3-[(E)-2-(2,4-Dinitrophenyl)ethenyl]-8-oxo-7α-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Nitrocefin (>90%)

(6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

NITROCEFIN

3-[(E)-2-(2,4-Dinitrophenyl)vinyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Nitrocefin (&gt

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(1E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7R)-

Cefnitrothiophene

(6R,7R)-7-[[(E)-4-(2,4-Dinitrophenyl)-2-(2-thienyl)but-3-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Nitrocefin, Chromogenic cephalosporin beta-lactamase substrate

41906-86-9

C21H16N4O8S2

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