41906-86-9 Usage
Description
NITROCEFIN is a chromogenic cephalosporin substrate that is commonly used to detect β-lactamases in bacteria. It is sensitive to hydrolysis by all known lactamases produced by both Gram-positive and Gram-negative bacteria. The presence of β-lactamase activity is indicated by a color change from yellow to red, which is proportional in intensity to the original concentration of nitrocefin.
Uses
Used in Antibiotic Resistance Detection:
NITROCEFIN is used as a detection agent for β-lactamase activity in bacteria, which is responsible for resistance to several classes of β-lactam antibiotics, including penicillins and cephalosporins. The color change from yellow to red as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase helps in identifying the presence of β-lactamase activity.
Used in Bacterial Cell Extract Analysis:
NITROCEFIN is used as an analytical tool for the detection of β-lactamase activity from bacterial cell extracts through isoelectric focusing and spectroscopy. This helps in understanding the resistance mechanisms of bacteria to β-lactam antibiotics.
Used in β-lactamase Resistant Antibiotic Studies:
NITROCEFIN is used as a research tool in studies involving β-lactamase resistant antibiotics. The color change properties of NITROCEFIN allow for the evaluation of the effectiveness of these antibiotics against bacteria producing β-lactamases.
Used in Solution Preparation and Color Change Analysis:
NITROCEFIN is used in the preparation of solutions for the detection of β-lactamase activity. The yellow color of intact, undegraded nitrocefin indicates its presence before exposure to β-lactamase. The red color resulting from the β-lactamase-mediated cleavage of nitrocefin is used to confirm the presence of β-lactamase activity.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 41906-86-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,1,9,0 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 41906-86:
(7*4)+(6*1)+(5*9)+(4*0)+(3*6)+(2*8)+(1*6)=119
119 % 10 = 9
So 41906-86-9 is a valid CAS Registry Number.
InChI:InChI=1/C21H16N4O8S2/c26-16(9-14-2-1-7-34-14)22-17-19(27)23-18(21(28)29)12(10-35-20(17)23)4-3-11-5-6-13(24(30)31)8-15(11)25(32)33/h1-8,17,20H,9-10H2,(H,22,26)(H,28,29)/b4-3+/t17-,20-/m1/s1
41906-86-9Relevant articles and documents
Nitrocefin synthesis method
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, (2017/04/08)
The invention relates to a nitrocefin synthesis method and belongs to the field of drug synthesis. The invention provides a novel process for preparing nitrocefin from a compound I as a raw material. The compound I is prepared from 7-ACA. The nitrocefin synthesis method can realize synthesis of nitrocefin from 7-ACA as an initial raw material through seven processes. The 7-ACA as an initial raw material is a key intermediate of a cephalosporin, has already been industrialized and has a low market price. The nitrocefin synthesis method has the advantages of simple processes, easy reaction treatment, easy product purification, high yield, easy industrialization and low production cost.
Synthesis of the β-lactamase indicators Cefesone and Nitrocefin
Barendse, Nico C. M. E.,Van Der Klein, Pieter A. M.,Verweij, Jan,Witkamp, Henk A.,Van Zoest, Wim J.,De Vroom, Erik
, p. 145 - 147 (2007/10/03)
The synthesis of the β-lactamase indicators Cefesone [(6R,7R)-3-(2,4- dinitrostyryl)-7-(phenylacetamido)ceph-3-em-4-carboxylic acid] and Nitrocefin [(6R,7R)-3-(2,4-dinitrostyryl)-7-(2-thienylacetamido)ceph-3-em-4-carboxylic acid] from tert-butyl (1S,6R,7R)-3-bromomethyl-1-oxo-7-(phenylacetamido)ceph- 3-em-4-carboxylate is reported. Phosphonylation of the latter compound with triphenylphosphine gave the corresponding phosphonium derivative in 93% yield. Reduction followed by Wittig coupling with 2,4-dinitrobenzaldehyde gave a 1:12 mixture of E- and Z-isomers in 83% yield. The tert-butyl protecting group was removed with titanium tetrachloride to give Cefesone as the pure crystalline E-isomer in 63% yield. De-acylation was achieved by enzymatic hydrolysis in 77% yield. Finally the 2-thienylacetyl side chain was introduced to give crystalline Nitrocefin in 67% yield.
