Oxidation of β-lactam antibiotics by peracetic acid: Reaction kinetics, product and pathway evaluation

Zhang, Kejia; Zhou, Xinyan; Du, Penghui; Zhang, Tuqiao; Cai, Meiquan; Sun, Peizhe; Huang, Ching-Hua

doi:10.1016/j.watres.2017.06.057

Cited by 149 publications

(65 citation statements)

References 41 publications

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“…This is probably explained by their lower stability which may make it more difficult for bacteria to adapt to the biocidal agents. Another advantage for peracetic acid in this context is that it was able to transform different beta-lactam antibiotics in wastewater at concentrations of 0.0005–0.002% which may help to reduce antibiotic selection pressure in wastewater [75].…”

Section: Other Biocidal Agentsmentioning

confidence: 99%

Biocidal Agents Used for Disinfection Can Enhance Antibiotic Resistance in Gram-Negative Species

2018

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Biocidal agents used for disinfection are usually not suspected to enhance cross-resistance to antibiotics. The aim of this review was therefore to evaluate the effect of 13 biocidal agents at sublethal concentrations on antibiotic resistance in Gram-negative species. A medline search was performed for each biocidal agent on antibiotic tolerance, antibiotic resistance, horizontal gene transfer, and efflux pump. In cells adapted to benzalkonium chloride a new resistance was most frequently found to ampicillin (eight species), cefotaxime (six species), and sulfamethoxazole (three species), some of them with relevance for healthcare-associated infections such as Enterobacter cloacae or Escherichia coli. With chlorhexidine a new resistance was often found to ceftazidime, sulfamethoxazole and imipenem (eight species each) as well as cefotaxime and tetracycline (seven species each). Cross-resistance to antibiotics was also found with triclosan, octenidine, sodium hypochlorite, and didecyldimethylammonium chloride. No cross-resistance to antibiotics has been described after low level exposure to ethanol, propanol, peracetic acid, polyhexanide, povidone iodine, glutaraldehyde, and hydrogen peroxide. Taking into account that some biocidal agents used in disinfectants have no health benefit (e.g., in alcohol-based hand rubs) but may cause antibiotic resistance it is obvious to prefer products without them.

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Section: Other Biocidal Agentsmentioning

confidence: 99%

Biocidal Agents Used for Disinfection Can Enhance Antibiotic Resistance in Gram-Negative Species

2018

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“…Various strategies have been designed to terminate activity after excretion, including photodegradation and oxidation with disinfectants such as chlorine, ozone, or peracetic acid. The reaction of β‐lactams with ozone and peracetic acid have revealed a similar trail as the degradation products from those reactions were generated from the sulfoxide intermediates …”

Section: Sulfides → Sulfoxidesmentioning

confidence: 99%

Interconnection of sulfides and sulfoxides in medicinal chemistry

Surur

Schulig

Link

2018

Arch. Pharm. Chem. Life Sci.

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Aromatic heterocycles with basic nitrogen atoms as well as carboxylic acid derivatives are the dominating chemical space in the universe of drug-like molecules. These established and exceedingly evaluated structural motifs have to be combined with elements of diversity in order to chart less well-explored galaxies of chemical space and to be able to tackle seemingly undruggable targets. Flat scaffolds should be replaced by shapely molecular cores. In this context, it has been unheeded that phenyl rings in diaryl sulfides are less co-planar than in ethers and that the metabolic interconnection of sulfides and sulfoxides offers advantages that are unalike from the chemistry of amines and N-oxides in the CHN-O world. Moreover, σ-hole potentials increase with the polarizability of the atom N < P < O < S and do not only play a role in long-time overlooked halogen bonds. Examples for λ 2 , λ 4 , and λ 6 S-based functionalities related to improved solubility, reduced drug resistance, linkers in drug conjugates, drugtargeting to parasites, and as basis for drug monitoring in sports are given and discussed. K E Y W O R D Santituberculosis activity, inhibitors, oxidation kinetics, rational drug design, sulfides, sulfoxides Arch Pharm Chem Life Sci. 2019;352:e1800248.wileyonlinelibrary.com/journal/ardp

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“…PAA can directly oxidize some organic contaminants in wastewater treatment, e.g., amino acid [25] and β-lactam antibiotics [26]. After the introduction of intensive energy (e.g., heat and UV) or catalysts, the peroxide bond in PAA can be activated to produce reactive species (e.g., HO • and R-O • ) [19,[27][28][29].…”

Section: Introductionmentioning

confidence: 99%

“…After the introduction of intensive energy (e.g., heat and UV) or catalysts, the peroxide bond in PAA can be activated to produce reactive species (e.g., HO • and R-O • ) [19,[27][28][29]. Compared with the inorganic peroxides, e.g., H 2 O 2 (213 kJ mol −1 ), PAA has a weaker -O-O-bond (159 kJ mol −1 for PAA [26,30]), which can be easily activated for intensive radical generation to attack target contaminants, such as pharmaceuticals [19,31], phenols [27,32], and dyes [33]. Therefore, PAA shows a great potential to be an ideal alternative to H 2 O 2 in AOPs and the development of efficient and environmentally friendly methods to activate PAA is of great significance.…”

Section: Introductionmentioning

confidence: 99%

Activation of Peracetic Acid with Lanthanum Cobaltite Perovskite for Sulfamethoxazole Degradation under a Neutral pH: The Contribution of Organic Radicals

Zhou

Zhang

et al. 2020

Molecules

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Advanced oxidation processes (AOPs) are effective ways to degrade refractory organic contaminants, relying on the generation of inorganic radicals (e.g., •OH and SO4•−). Herein, a novel AOP with organic radicals (R-O•) was reported to degrade contaminants. Lanthanum cobaltite perovskite (LaCoO3) was used to activate peracetic acid (PAA) for organic radical generation to degrade sulfamethoxazole (SMX). The results show that LaCoO3 exhibited an excellent performance on PAA activation and SMX degradation at neutral pH, with low cobalt leaching. Meanwhile, LaCoO3 also showed an excellent reusability during PAA activation. In-depth investigation confirmed CH3C(O)O• and CH3C(O)OO• as the key reactive species for SMX degradation in LaCoO3/PAA system. The presence of Cl− (1–100 mM) slightly inhibited the degradation of SMX in the LaCoO3/PAA system, whereas the addition of HCO3− (0.1–1 mM) and humic aid (1–10 mg/L) could significantly inhibit SMX degradation. This work highlights the generation of organic radicals via the heterogeneous activation of PAA and thus provides a promising way to destruct contaminants in wastewater treatment.

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Oxidation of β-lactam antibiotics by peracetic acid: Reaction kinetics, product and pathway evaluation

Cited by 149 publications

References 41 publications

Biocidal Agents Used for Disinfection Can Enhance Antibiotic Resistance in Gram-Negative Species

Biocidal Agents Used for Disinfection Can Enhance Antibiotic Resistance in Gram-Negative Species

Interconnection of sulfides and sulfoxides in medicinal chemistry

Activation of Peracetic Acid with Lanthanum Cobaltite Perovskite for Sulfamethoxazole Degradation under a Neutral pH: The Contribution of Organic Radicals

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