Adsorption and transformation of selected human-used macrolide antibacterial agents with iron(III) and manganese(IV) oxides

Environ Pollut. 2009 Apr;157(4):1317-22. doi: 10.1016/j.envpol.2008.11.048. Epub 2008 Dec 27.

Abstract

The adsorption/transformation of two members (clarithromycin and roxithromycin) of the macrolide (ML) antibacterial agents on the surface of three environmental subsurface sorbents (clay, iron(III) and manganese(IV) oxy-hydroxides) was investigated. The adsorption fitted well to the Freundlich model with a high sorption capacity. Adsorption probably occurred through a surface complexation mechanism and was accompanied by slow degradation of the selected MLs. Transformation proceeded through two parallel pathways: a major pathway was the hydrolysis of the cladinose sugar, and to a lesser extent the hydrolysis of the lactone ring. A minor pathway was the N-dealkylation of the amino sugar. This study indicates that Fe(III) and Mn(IV) oxy-hydroxides in aquatic sediments may play an important role in the natural attenuation of MLs. Such an attenuation route yields a range of intermediates that might retain some of their biological activity.

MeSH terms

  • Adsorption
  • Aluminum Silicates
  • Anti-Bacterial Agents / chemistry*
  • Biodegradation, Environmental
  • Clarithromycin / chemistry
  • Clay
  • Ecology / methods
  • Ferric Compounds / chemistry
  • Macrolides / chemistry*
  • Manganese Compounds / chemistry
  • Oxides / chemistry
  • Roxithromycin / chemistry
  • Soil / analysis
  • Soil Pollutants / chemistry*
  • Surface Properties

Substances

  • Aluminum Silicates
  • Anti-Bacterial Agents
  • Ferric Compounds
  • Macrolides
  • Manganese Compounds
  • Oxides
  • Soil
  • Soil Pollutants
  • ferric oxide
  • Roxithromycin
  • manganese oxide
  • Clarithromycin
  • Clay