Nitrocefin
- CAS NO.:41906-86-9
- Empirical Formula: C21H16N4O8S2
- Molecular Weight: 516.5
- MDL number: MFCD12165893
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-09-09 11:20:40
What is Nitrocefin?
Description
The generation of β-
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).
The Uses of Nitrocefin
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.
What are the applications of Application
Nitrocefin is a chromogenic cephalosporin substrate, commonly used to detect β-lactamases in bacteria.
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.
Properties of Nitrocefin
Melting point: | 103-113° (dec); mp 167-169° (dec) (Lee) |
Boiling point: | 872.0±65.0 °C(Predicted) |
alpha | D20 -224° (c = 1.0 in dioxane) |
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 |
Safety information for Nitrocefin
Signal word | Warning |
Pictogram(s) |
Flame Flammables GHS02 |
GHS Hazard Statements |
H228:Flammable solids |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P260:Do not breathe dust/fume/gas/mist/vapours/spray. |
Computed Descriptors for Nitrocefin
Abamectin manufacturer
SRI ANAGHA BIOSCIENCES PVT LTD
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