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
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
Safety
- HS Code
- 29349990
N-Bromosuccinimide Price
- 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
- Product number
- 15424
- Product name
- Nitrocefin
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $85
- Updated
- 2024/03/01
- Product number
- 15424
- Product name
- Nitrocefin
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $148
- Updated
- 2024/03/01
- Product number
- 15424
- Product name
- Nitrocefin
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $253
- Updated
- 2024/03/01
- Product number
- 15424
- Product name
- Nitrocefin
- Purity
- ≥95%
- Packaging
- 25mg
- Price
- $527
- Updated
- 2024/03/01
Nitrocefin Chemical Properties,Usage,Production
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).
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
- 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
- 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
- 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