Nitrocefin

Structural formula
General
Surname	Nitrocefin
other names	(7 R ) -3 - (( E ) -2,4-Dinitrostyryl) -7- (2-thienylacetamido) -3-cephem-4-carboxylic acid
Molecular formula	C 21 H 16 N 4 O 8 S 2
Brief description	yellow-orange solid
External identifiers / databases
EC number	636-988-0
ECHA InfoCard	100.164.734
PubChem	6436140
ChemSpider	4940809
DrugBank	DB11592
Wikidata	Q1993962
properties
Molar mass	516.5 g mol −1
Physical state	firmly
Melting point	167-169 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitrocefin is a substance belonging to the chemical group of the cephalosporins , which changes its color from yellow to red when split by β-lactamases .

Properties and use

The pure substance dissolves well in dimethyl sulfoxide . She is sensitive to light. It was first isolated from the Acremonium mold discovered by Giuseppe Brotzu .

Nitrocefin is a chromogenic cephalosporin : when the β- lactam ring is hydrolytically opened, the absorption maximum shifts from 390 nm to 486 nm, which is accompanied by a color change from yellow to red. Nitrocefin is therefore suitable for the detection of bacteria that produce β-lactamases. β-lactamases play an important role in the feared antibiotic resistance of bacteria. The test is more sensitive than the test previously carried out on the basis of bromocresol purple .

literature

JP Richard: Advances in Physical Organic Chemistry , Volume 41, 2006, p. 117 ( limited preview in Google book search)
Monica Cheesbrough: District Laboratory Practice in Tropical Countries , Volume 2, 2006, p. 142 ( limited preview in Google Book Search)
Victor Lorian: Antibiotics in laboratory medicine , 2005, p. 485 ( limited preview in Google book search)
Karin Hammann-Meyer: Investigations into the diagnostic value of Nitrocefin, 1981.

Individual evidence

↑ nugi center: Nitrocefin (PDF; 183 kB).
↑ Mijoon Lee, Dusan Hesek, Shahriar Mobashery: A Practical Synthesis of Nitrocefin. In: The Journal of Organic Chemistry. 70, 2005, pp. 367-369, doi : 10.1021 / jo0487395 .
↑ ^a ^b Data sheet Nitrocefin - CAS 41906-86-9 - Calbiochem, 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. at Sigma-Aldrich , accessed on December 21, 2019 ( PDF ).
^ GA Papanicolaou, AA Medeiros: Discrimination of extended-spectrum beta-lactamases by a novel nitrocefin competition assay. In: Antimicrobial agents and chemotherapy. Volume 34, Number 11, November 1990, pp. 2184-2192, PMID 2073109 , PMC 172021 (free full text).

[1] ugi center: Nitrocefin (PDF; 183 kB).

[2] Mijoon Lee, Dusan Hesek, Shahriar Mobashery: A Practical Synthesis of Nitrocefin. In: The Journal of Organic Chemistry. 70, 2005, pp. 367-369, doi : 10.1021 / jo0487395 .

[Sigma-3] Data sheet Nitrocefin - CAS 41906-86-9 - Calbiochem, 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. at Sigma-Aldrich , accessed on December 21, 2019 ( PDF ).

[4] GA Papanicolaou, AA Medeiros: Discrimination of extended-spectrum beta-lactamases by a novel nitrocefin competition assay. In: Antimicrobial agents and chemotherapy. Volume 34, Number 11, November 1990, pp. 2184-2192, PMID 2073109 , PMC 172021 (free full text).