| Identification | Back Directory | [Name]
NITROCEFIN | [CAS]
41906-86-9 | [Synonyms]
NITROCEFIN
Nitrocefin (>
Nitrocefin (>90%)
3-(2,4-DINITROSTYRYL)-(6R, 7R)-7-(2-THIENYLACETAMIDO)-CEPH-3-EM-4 CARBOXYLIC ACID, E-ISOMER
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
(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)-
(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 | [Molecular Formula]
C21H16N4O8S2 | [MDL Number]
MFCD00864896 | [MOL File]
41906-86-9.mol | [Molecular Weight]
516.5 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [Description]
The generation of β-lactamases by bacteria affords resistance to several classes of β-lactam antibiotics, including penicillins and cephalosporins.1 Nitrocefin is a chromogenic cephalosporin substrate commonly used to detect β-lactamases in bacteria.2,3,4 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.2 | [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]
In determination of b-lactamase activity in biological samples. | [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. | [Uses]
sedative | [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. | [storage]
Store at -20°C |
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