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

Abstract

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.

Towards the Removal of Antibiotics Detected in Wastewaters in the POCTEFA Territory: Occurrence and TiO2 Photocatalytic Pilot-Scale Plant Performance

“…Amoxicillin was not found in any sample (influent and effluent of the WWTPs). This fact could be attributed to the low stability of amoxicillin and the subsequent generation of degradation products such as amoxicillin penicilloic acid or amoxicillin-diketopiperazine-2', 5', as is suggested in the literature [38][39][40]. These degradation products were found in subsequent campaigns carried out in the same sampling points.…”

Rapid monitoring of benzylpenicillin sodium using Raman and surface enhanced Raman spectroscopy

“…These changes must be derived from the structural alterations of benzylpenicillin. It is because that NaBP easily opens its b-lactam ring to produce penicilloic acid and penilloaldehyde in acidic condition and generate penicilloic acid and penilloic acid in alkaline environment [25], which result in the decrease of Raman intensity at 1000 cm À1 and the appearing of new Raman bands. The chemical structures of penicilloic acid, penilloaldehyde and penilloic acid are shown in Fig.…”

“…Penicillin is not stable either in acidic or alkaline environments and the decomposition reaction is very complicated due to the diversification of products and the incompleteness of reactions. Penicilloic acid is a major allergen causing the fatal immune responses [25][26][27][28]. It is obvious that SERS can be used to detect whether there are other substances presenting in the penicillin (or whether there are ring-opening reactions occurring), which is helpful to reduce the occurrence of allergic reactions.…”

A novel platform test to detect beta-lactam residues in raw milk

“…This mechanism is followed by beta-lactamases of molecular classes A, C, and D, but class B enzymes utilize a zinc ion to attack the beta-lactam ring (Bonomo, 2017). Li et al (2014) carried out research on degradation of penicillin in raw milk by beta-lactamase enzyme using ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry. In their study, betalactamase enzyme and penicillin were spiked in raw milk samples.…”