Tandem mass spectrometric studies of the fragmentation of penicillins and their metabolites

Abstract

The fragmentation of two penicillins, ampicillin and amoxicillin, and their principal metabolites has been studied by a combination of liquid chromatography/thermospray mass spectrometry and tandem mass spectrometry. A high-resolution tandem mass spectrometer was used to obtain chemical ionization, fast-atom bombardment, and collision-induced dissociation mass spectra. Structural information and fragmentation mechanisms have been deduced from ions in the mass and collision spectra. This knowledge is useful in the analysis and identification of metabolites of ampicillin and related drugs in human body fluids.

Metabolic Profiling and In Vitro Assessment of the Biological Activities of the Ethyl Acetate Extract of Penicillium chrysogenum “Endozoic of Cliona sp. Marine Sponge” from the Red Sea (Egypt)

“…The MS 2 spectrum ( Figure 2 E) showed a prominent molecular ion peak at m/z 356.1262 and 356.9433 [M + Na] + , respectively, and fragment ions at m/z 217 [M + H-C 8 H 7 O] + and m/z 176 [M + H-C 6 H 9 O 2 NS] + , which showed the loss of the thiazolidine ring. The mass data of these compounds are in good agreement with those in the literature of penicillin G along with its stereoisomers [ 34 ]. Penicillin G was also isolated from P. chrysogenum endophytic fungus on the mangrove plant Porteresia coarctata (Roxb.)…”

Antibiotic removal from wastewaters: The ozonation of amoxicillin

“…5) is typical for protonated amoxicillin [34]. The apperance of several observed ions may be interpreted by the loss of neutral fragments or by the cleavage and loss of aliphatic fragments in side-chains as follows: 365 due to a loss of neutral NH 3 typical for penicillins [34]; 350 (loss of neutral NH 3 and/or OH-and in addition -CH 3 ); 336 (loss of H 2 O and CO); 306 (loss of H 2 O + CO 2 + CH 2 -or NH 3 + CO 2 + -CH 3 ) and 293 (loss of CO 2 + NH 3 + 2x CH 2 -). Both the results from the UV and especially MS experiments do not support the presence of noticeable quantity of amoxicillin sulfoxide (structure II, above).…”

Utility of surface enhanced Raman spectroscopy (SERS) for elucidation and simultaneous determination of some penicillins and penicilloic acid using hydroxylamine silver nanoparticles

“…However, allergic test is an important procedure prior to its use because the allergic responses for patients are very serious and even fatal [1]. It has now reported that penicilloic acid (PCA) as the main degradation product of penicillin in storage through the opening β-lactam ring of penicillin is a major allergen causing the fatal immune responses by covalent conjugation with ε-amino groups of lysine residues of immunological proteins through penicilloyl groups [2]. In general, the residual amount of PCA less than 1.0% (w/w) in penicillin can significantly reduce the occurrence of allergic reactions.…”