НИТРОЦЕФИН
41906-86-9
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- CAS №
- 41906-86-9
- Химическое название:
- НИТРОЦЕФИН
- английское имя:
- Nitrocefin
- Синонимы:
- 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
- Формула:
- C21H16N4O8S2
- молекулярный вес:
- 516.5
- MOL File:
- 41906-86-9.mol
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НИТРОЦЕФИН атрибут
Температура плавления: |
103-113° (dec); mp 167-169° (dec) (Lee) |
альфа: |
D20 -224° (c = 1.0 in dioxane) |
Температура кипения: |
872.0±65.0 °C(Predicted) |
плотность: |
1.67±0.1 g/cm3(Predicted) |
температура хранения: |
2-8°C |
растворимость: |
DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:20): 0.04 mg/ml |
форма: |
Кристаллическое твердое вещество |
пка: |
2.50±0.50(Predicted) |
цвет: |
Yellow to orange |
Стабильность:: |
Hygroscopic, Unstable in Solution |
FDA UNII: |
EWP54G0J8F |
безопасность
- Заявления о рисках и безопасности
- код информации об опасности(GHS)
символ(GHS) |
|
сигнальное слово |
Warning |
Заявление об опасности |
пароль |
Заявление об опасности |
Класс опасности |
категория |
сигнальное слово |
пиктограмма |
предупреждение |
H228 |
Воспламеняющееся твердое вещество. |
Легковоспламеняющиеся твердые вещества |
Категория 1 Категория 2 |
Опасность Предупреждение |
![](/GHS02.jpg) |
P210, P240,P241, P280, P370+P378 |
|
Внимание |
P210 |
Беречь от тепла, горячих поверхностей, искр, открытого огня
и других источников воспламенения. Не курить. |
P260 |
Не вдыхать газ/ пары/ пыль/ аэрозоли/ дым/ туман. |
|
НИТРОЦЕФИН химические свойства, назначение, производство
Описание
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.
Химические свойства
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
![Solution preparation and color change before and after β-lactamase exposure Solution preparation and color change before and after β-lactamase exposure](/NewsImg/2022-02-21/6378105810652275602120540.jpg)
(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).
Использование
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.
Подготовка
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
Биологические функции
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.
НИТРОЦЕФИН препаратная продукция и сырье
сырьё
препарат
НИТРОЦЕФИН поставщик
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