Identification of Degradation Products of Erythromycin A Arising from Ozone and Advanced Oxidation Process Treatment

Abstract

The degradation products of the macrolide antibiotic erythromycin A (ERY) arising from direct ozone attack and hydroxyl radical attack are presented for the first time. Ozone treatment was carried out by spiking ozone stock solutions to solutions containing ERY-ERY:O 3 5 1:5 and 1:10 (M:M), while, in parallel, t-BuOH was used as a hydroxyl radical (NOH) scavenger. The advanced oxidation processes (AOPs) O 3 /UV, O 3 /H 2 O 2 , and UV/H 2 O 2 were carried out to recognize and verify possible differences between their primary degradation products; the initial concentrations were ERY:O 3 5 1:5 (M:M), ERY:O 3 :H 2 O 2 5 1:5:5 (M:M:M), or ERY:H 2 O 2 5 1:5 (M:M), respectively. Six degradation products were identified from ozonation-one originates from direct ozone attack on the tertiary amine group, while the others arise from radical ion attack, which might be formed during degradation of O 3 in water. Fewer primary degradation products were observed arising from NOH-based treatments (AOP) than from ozonation, possibly because the reaction of NOH radicals is non-selective and typically is diffusion-controlled. Four degradation products were detected by NOH radical attacks; two of them already were observed during ozonation, with one as an oxidized ERY molecule and the other as a non-oxidized fragment of the ERY molecule. Water Environ. Res., 82, 797 (2010).

Identification of new transformation products during enzymatic treatment of tetracycline and erythromycin antibiotics at laboratory scale by an on-line turbulent flow liquid-chromatography coupled to a high resolution mass spectrometer LTQ-Orbitrap

“…Similar pattern is observed for ERY (macrolide), which also has been described to affect the resistance of bacterial communities in activated sludge (Li and Zhang, 2010) but, in contrast, not in biofilms at environmental relevant concentrations (Wunder et al, 2013). Because of these problems, different authors have studied an alternative degradation processes for both compounds as well as the generation of any transformation products (Tc (Halling-Sørensen et al, 2002;Parka and Chounga, 2007;Chen and Huang, 2010;Khan et al, 2010) and ERY (Kim et al, 2004a(Kim et al, , 2004bLuiz et al, 2010;Pengelly, 2010)). …”

Transformation of pharmaceuticals during oxidation/disinfection processes in drinking water treatment

“…11). Five other oxidation products, which resulted from reaction with HO•, were also identified [55]. Radjenovic et al [56] reported ozonation products of roxithromycin, which mostly involved HO• reactions.…”

“…A demethylated product also occurs for ozone reactions with erythromycin, which results from direct ozone attack on the tertiary amine group [55] (Fig. 11).…”

“…Reaction of the desosamine sugar of the erythromycin molecule with ozone to form de-methylated erythromycin and formaldehyde (adapted from Luiz et al[55]). …”

A Review of Combined Advanced Oxidation Technologies for the Removal of Organic Pollutants from Water

“…The water quality deterioration is increasing due to increase discharge of wastewater containing recalcitrant, inhibitory pollutants into the immediate environment (Khan et al 2009;Chong et al 2010). Thus, higher concentrations of these pollutants are expected to be aggravated in the nearest future due to the ever-increasing pollution index (Luiz et al 2010). A study has shown that the variation in the concentration of contaminants detected in water could be ascribed to different consumption pattern across countries (Luiz et al 2011).…”