(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
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- CAS番号.
- 41906-86-9
- 化学名:
- (6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
- 别名:
- ニトロセフィン;(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸;(6R,7R)-3-[(1E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7-[2-(チオフェン-2-イル)アセトアミド]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
- 英語名:
- Nitrocefin
- 英語别名:
- 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
- 化学式:
- C21H16N4O8S2
- 分子量:
- 516.5
- MOL File:
- 41906-86-9.mol
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(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸 物理性質
- 融点 :
- 103-113° (dec); mp 167-169° (dec) (Lee)
- 比旋光度 :
- D20 -224° (c = 1.0 in dioxane)
- 沸点 :
- 872.0±65.0 °C(Predicted)
- 比重(密度) :
- 1.67±0.1 g/cm3(Predicted)
- 貯蔵温度 :
- 2-8°C
- 溶解性:
- DMF: 20 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:20): 0.04 mg/ml
- 外見 :
- A crystalline solid
- 酸解離定数(Pka):
- 2.50±0.50(Predicted)
- 安定性::
- Hygroscopic, Unstable in Solution
安全性情報
- リスクと安全性に関する声明
- 危険有害性情報のコード(GHS)
絵表示(GHS) |
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注意喚起語 |
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危険有害性情報 |
コード |
危険有害性情報 |
危険有害性クラス |
区分 |
注意喚起語 |
シンボル |
P コード |
H228 |
可燃性固体 |
可燃性固体 |
1 2 |
危険 警告 |
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P210, P240,P241, P280, P370+P378 |
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注意書き |
P210 |
熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。 |
P260 |
粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。 |
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(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸 価格
もっと(6)
メーカー |
製品番号 |
製品説明 |
CAS番号 |
包装 |
価格 |
更新時間 |
購入 |
富士フイルム和光純薬株式会社(wako)
|
W01CAY15424 |
Nitrocefin |
41906-86-9 |
1mg |
¥23800 |
2024-03-01 |
購入 |
富士フイルム和光純薬株式会社(wako)
|
W01CAY15424 |
Nitrocefin |
41906-86-9 |
5mg |
¥41400 |
2024-03-01 |
購入 |
富士フイルム和光純薬株式会社(wako)
|
W01CAY15424 |
Nitrocefin |
41906-86-9 |
25mg |
¥147600 |
2024-03-01 |
購入 |
関東化学株式会社(KANTO)
|
713112-5 |
ニトロセフィンNitrocefin
Nitrocefin |
41906-86-9 |
2mL×5本 |
¥77000 |
2024-03-01 |
購入 |
富士フイルム和光純薬株式会社(wako)
|
W01CAY15424 |
Nitrocefin |
41906-86-9 |
10mg |
¥70800 |
2024-03-01 |
購入 |
(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸 化学特性,用途語,生産方法
説明
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.
化学的特性
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).
使用
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.
製造方法
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
生物学の機能
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.
(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸 上流と下流の製品情報
原材料
準備製品
(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸 生産企業
Global( 108)Suppliers
(6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸 スペクトルデータ(MS)
41906-86-9((6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸)キーワード:
- 41906-86-9
- 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
- ニトロセフィン
- (6R)-3-[(E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7α-[(2-チエニルアセチル)アミノ]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸
- (6R,7R)-3-[(1E)-2-(2,4-ジニトロフェニル)エテニル]-8-オキソ-7-[2-(チオフェン-2-イル)アセトアミド]-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸