Persistence and degradation of new β-lactam antibiotics in the soil and water environment

• Hydrolysis of two new monocyclic β-lactam antibiotics in the pH range 3–9.
• Identification of hydrolysis products and hydrolytic pathway.
• Persistence in a calcareous soil at wilting point and field capacity.
• Persistence in a forest acidic soil at wilting point and field capacity.
• Degradation pathways in soils.

The development of new antibiotics with low environmental persistence is of utmost importance in contrasting phenomena of antibiotic resistance. In this study, the persistence of two newly synthesized monocyclic β-lactam antibiotics: (2R)-1-(methylthio)-4-oxoazetidin-2-yl acetate, P1, and (2R,3R)-3-((1R)-1-(tert-butyldimethylsilanyloxy)ethyl)-1-(methylthio)-4-oxoazetidin-2-yl acetate, P2, has been investigated in water in the pH range 3–9 and in two (calcareous and forest) soils, then compared to amoxicillin, a β-lactam antibiotic used in human and veterinary medicine. P1 and P2 persistence in water was lower than that of amoxicillin with only a few exceptions. P1 hydrolysis was catalyzed at an acidic pH whereas P2 hydrolysis takes place at both acidic and alkaline pH values. P1 persistence in soils depended mainly on their water potential (t1/2: 35.0–70.7 d at wilting point; <1 d at field capacity) whereas for P2 it was shorter and unaffected by soil water content (t1/2 0.13–2.5 d). Several degradation products were detected in soils at both water potentials, deriving partly from hydrolytic pathways and partly from microbial transformation. The higher Log Kow value for P2 compared with P1 seemingly confers P2 with high permeability to microbial membranes regardless of soil water content. P1 and P2 persistence in soils at wilting point was shorter than that of amoxicillin, whereas it had the same extent at field capacity.

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