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 beta-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 beta-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 (t(1/2): 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 (t(1/2) 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 LogK(ow) 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

Persistence and degradation of new β-lactam antibiotics in the soil and water environment / Braschi I.; Blasioli S.; Fellet C.; Lorenzini R.; Garelli A.; Pori M.; Giacomini D.. - In: CHEMOSPHERE. - ISSN 0045-6535. - STAMPA. - 93:1(2013), pp. 152-159. [10.1016/j.chemosphere.2013.05.016]

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

BRASCHI, ILARIA;BLASIOLI, SONIA;LORENZINI, RITA;GARELLI, ANDREA;PORI, MATTEO;GIACOMINI, DARIA
2013

Abstract

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 beta-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 beta-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 (t(1/2): 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 (t(1/2) 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 LogK(ow) 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
2013
Persistence and degradation of new β-lactam antibiotics in the soil and water environment / Braschi I.; Blasioli S.; Fellet C.; Lorenzini R.; Garelli A.; Pori M.; Giacomini D.. - In: CHEMOSPHERE. - ISSN 0045-6535. - STAMPA. - 93:1(2013), pp. 152-159. [10.1016/j.chemosphere.2013.05.016]
Braschi I.; Blasioli S.; Fellet C.; Lorenzini R.; Garelli A.; Pori M.; Giacomini D.
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/265096
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? 10
  • Scopus 74
  • ???jsp.display-item.citation.isi??? 66
social impact