Nitrocefin
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- CAS-Nr.
- 41906-86-9
- Englisch Name:
- Nitrocefin
- Synonyma:
- 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;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)-;(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
- CBNumber:
- CB1322600
- Summenformel:
- C21H16N4O8S2
- Molgewicht:
- 516.5
- MOL-Datei:
- 41906-86-9.mol
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Nitrocefin Eigenschaften
- Schmelzpunkt:
- 103-113° (dec); mp 167-169° (dec) (Lee)
- alpha
- D20 -224° (c = 1.0 in dioxane)
- Siedepunkt:
- 872.0±65.0 °C(Predicted)
- Dichte
- 1.67±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- L?slichkeit
- DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:20): 0.04 mg/ml
- Aggregatzustand
- A crystalline solid
- pka
- 2.50±0.50(Predicted)
- Farbe
- Yellow to orange
- Stabilit?t:
- 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
Sicherheit
- Risiko- und Sicherheitserkl?rung
- Gefahreninformationscode (GHS)
| Bildanzeige (GHS) |
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| Alarmwort |
Warnung |
| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H228 |
Entzündbarer Feststoff. |
Entzündbare Feststoffe |
Kategorie 1 |
Achtung
Warnung |
![GHS hazard pictograms]() src="/GHS02.jpg" width="20" height="20" /> |
P210, P240,P241, P280, P370+P378 |
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| Sicherheit |
| P210 |
Von Hitze, hei?en Oberfl?chen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen. |
| P260 |
Dampf/Aerosol/Nebel nicht einatmen. |
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Nitrocefin Chemische Eigenschaften,Einsatz,Produktion Methoden
Beschreibung
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.
Chemische Eigenschaften
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).
Verwenden
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.
synthetische
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
Biologische Funktion
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 Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
Nitrocefin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 115)Lieferanten
41906-86-9()Verwandte Suche:
- 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
- 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)-
- 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
- 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
- 41906-86-9
- C21H16N4O8S2
- APIs
