Research on degradation of penicillins in milk by β-lactamase using ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry.

The degradation of penicillin G, penicillin V, and ampicillin in milk in the presence of β-lactamase was investigated by ultra-performance liquid chromatography coupled with electrospray ionization-time-of-flight mass spectrometry. Degradation products of the 3 penicillins in milk were identified based on the fact that the metabolites or degradation products contain a substructure of penicillin, and their degradation pathways in acidic milk in presence of β-lactamase were developed. The influence of factors on the degradation was investigated, including β-lactamase dosage, temperature, time, and acidity. The ratio of the 2 degradation products (penicilloic acid and penilloic acid) is different at different temperatures and pH. Penicilloic acid was the dominant species obtained at pH 6 under 40°C, but, being unstable, it could not be used as a standard for accurate analysis of penicilloic acid, and also could not be used as target for detection of penicillins in milk. Penilloic acid was the dominant species obtained at pH 2 above 40°C; it was stable and could be used as a standard for quantitative analysis and as target for detecting whether penicillins were used in milk.

[1]  Liqiang Liu,et al.  Detection of β-Lactamase Residues in Milk by Sandwich ELISA , 2013, International journal of environmental research and public health.

[2]  C. Cruces‐Blanco,et al.  Advances in the determination of β-lactam antibiotics by liquid chromatography , 2012 .

[3]  O. Chailapakul,et al.  High performance liquid chromatography for the simultaneous analysis of penicillin residues in beef and milk using ion-paired extraction and binary water-acetonitrile mixture. , 2012, Talanta.

[4]  Ligang Chen,et al.  Determination of β-lactam antibiotics in milk based on magnetic molecularly imprinted polymer extraction coupled with liquid chromatography-tandem mass spectrometry. , 2010, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[5]  Shuo Wang,et al.  Development of an enzyme-linked immunosorbent assay to detect benzylpenicilloic acid, a degradation product of penicillin G in adulterated milk. , 2010, Journal of agricultural and food chemistry.

[6]  Yinlong Guo,et al.  Determination of beta-lactamase residues in milk using matrix-assisted laser desorption/ionization Fourier transform mass spectrometry. , 2010, Analytical chemistry.

[7]  K. Carlson,et al.  Trace determination of beta-lactam antibiotics in surface water and urban wastewater using liquid chromatography combined with electrospray tandem mass spectrometry. , 2006, Journal of chromatography. A.

[8]  C. Fagerquist,et al.  Confirmatory and quantitative analysis of beta-lactam antibiotics in bovine kidney tissue by dispersive solid-phase extraction and liquid chromatography-tandem mass spectrometry. , 2005, Analytical chemistry.

[9]  A. Rytz,et al.  Cold-temperature stability of five beta-lactam antibiotics in bovine milk and milk extracts prepared for liquid chromatography-electrospray ionization tandem mass spectrometry analysis. , 2004, Journal of chromatography. A.

[10]  E. Goldman Antibiotic Abuse in Animal Agriculture: Exacerbating Drug Resistance in Human Pathogens , 2004 .

[11]  K. Shea Antibiotic resistance: what is the impact of agricultural uses of antibiotics on children's health? , 2003, Pediatrics.

[12]  G. Varisco,et al.  Residues of β-lactam antibiotics in bovine milk: confirmatory analysis by liquid chromatography tandem mass spectrometry after microbial assay screening , 2003, Food additives and contaminants.

[13]  K. Baert,et al.  Quantitative analysis of amoxycillin and its major metabolites in animal tissues by liquid chromatography combined with electrospray ionization tandem mass spectrometry. , 2002, Analytical chemistry.

[14]  B. Puschner,et al.  Screening and mass spectral confirmation of beta-lactam antibiotic residues in milk using LC-MS/MS. , 2002, Journal of agricultural and food chemistry.

[15]  E. Schmid,et al.  Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization , 2001, Fresenius' journal of analytical chemistry.

[16]  R. Stadler,et al.  Simultaneous Determination of Five β-Lactam Antibiotics in Bovine Milk Using Liquid Chromatography Coupled with Electrospray Ionization Tandem Mass Spectrometry , 2001 .

[17]  E. Daeseleire,et al.  Confirmatory assay for the simultaneous detection of penicillins and cephalosporins in milk using liquid chromatography/tandem mass spectrometry. , 2000, Rapid communications in mass spectrometry : RCM.

[18]  A. Kheirolomoom,et al.  The combined effects of pH and temperature on penicillin G decomposition and its stability modeling , 1999 .

[19]  A. Dayan Allergy to antimicrobial residues in food: assessment of the risk to man. , 1993, Veterinary microbiology.

[20]  R. B. Freas,et al.  Identification of metabolites of ampicillin using liquid chromatography/thermospray mass spectrometry and fast atom bombardment tandem mass spectrometry. , 1989, Biomedical & environmental mass spectrometry.

[21]  M. Page The Mechanisms of Reactions of β-Lactam Antibiotics , 1984 .

[22]  M. Page,et al.  The mechanisms of reactions of .beta.-lactam antibiotics , 1984 .

[23]  S. Hem,et al.  Kinetic analysis of penicillin degradation in acidic media. , 1976, Journal of pharmaceutical sciences.

[24]  J. Hou,et al.  -lactam antibiotics: their physicochemical properties and biological activities in relation to structure. , 1971, Journal of Pharmacy and Science.

[25]  Ma Li-li Simultaneous determination of 14 penicillins and penicilloic acids in milk by UPLC-MS/MS , 2012 .

[26]  Liu Chuang Simultaneous Determination of 2 Penicillins and Their 5 Major Metabolites in Bovine Muscle by Ultra Performance Liquid Chromatography Tandem Mass Spectrometry , 2011 .

[27]  Wei Wei Fast determination of 19 β-lactams and its metabolites in milk by ultra-performance liquid chromatography-tandem mass spectrometry and dispersion solid-phase extraction , 2010 .

[28]  P. de Backer,et al.  Rapid method for the quantification of amoxicillin and its major metabolites in pig tissues by liquid chromatography-tandem mass spectrometry with emphasis on stability issues. , 2008, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[29]  M. Nindi,et al.  Determination of β-lactam residues in foodstuffs of animal origin using supported liquid membrane extraction and liquid chromatography–mass spectrometry , 2007 .

[30]  N. R. Chatterjee,et al.  Degradation of β-lactam antibiotics , 2004 .

[31]  Hubbert Wt,et al.  Residue prevention strategies in the United States. , 1993 .