Biodegradation of atenolol by an enriched nitrifying sludge: Products and pathways

Xu, Y; Radjenovic, J; Yuan, Z; Ni, BJ

Biodegradation of atenolol by an enriched nitrifying sludge: Products and pathways

Xu, Y Radjenovic, J Yuan, Z Ni, BJ

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Publication Type:: Journal Article
Citation:: Chemical Engineering Journal, 2017, 312 pp. 351 - 359
Issue Date:: 2017-01-01

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Field	Value	Language
dc.contributor.author	Xu, Y	en_US
dc.contributor.author	Radjenovic, J	en_US
dc.contributor.author	Yuan, Z	en_US
dc.contributor.author	Ni, BJ https://orcid.org/0000-0002-1129-7837	en_US
dc.date.issued	2017-01-01	en_US
dc.identifier.citation	Chemical Engineering Journal, 2017, 312 pp. 351 - 359	en_US
dc.identifier.issn	1385-8947	en_US
dc.identifier.uri	http://hdl.handle.net/10453/126661
dc.description.abstract	© 2016 Elsevier B.V. Biodegradation of β-blocker atenolol was investigated using an enriched nitrifying culture at controlled ammonium concentration and without ammonium addition. Analysis of the kinetics and structural elucidation of biodegradation products showed that atenolol biodegradation was found to be linked to the activity of nitrifying bacteria in the presence of ammonium. Atenolol was degraded cometabolically by ammonia-oxidizing bacteria (AOB), likely due to a broad substrate range of ammonia monooxygenase (AMO). Four products were formed during atenolol biodegradation with ammonia oxidation, including P267 (atenolol acid) and three new products P117 (1-isopropylamino-2-propanol), P167 (1-amino-3-phenoxy-2-propanol), and an unknown product P227 with a nominal molecular mass of 227. In comparison, only P267 and P227 were identified during atenolol biodegradation without ammonia oxidation. Follow-up experiments using atenolol acid as the parent compound indicated the formation of products P117, P167 and P227 in the presence of ammonium. Based on the products identified, a tentative biodegradation pathway of atenolol is suggested, which involves two steps independent of the presence of ammonium: i) microbial amide-bond hydrolysis to carboxyl group and formation of P267 (atenolol acid) and ii) a possible formation of P227 with its unidentified structure and other two cometabolically induced reactions: iii) breakage of ether bond in the alkyl side chain and formation of P117 and iv) a minor pathway through N-dealkylation and loss of acetamide moiety from the aromatic ring, yielding P167. This study provided an important insight regarding the biotransformation pathways under different metabolic conditions.	en_US
dc.relation.ispartof	Chemical Engineering Journal	en_US
dc.relation.isbasedon	10.1016/j.cej.2016.11.153	en_US
dc.subject.classification	Chemical Engineering	en_US
dc.title	Biodegradation of atenolol by an enriched nitrifying sludge: Products and pathways	en_US
dc.type	Journal Article
utslib.citation.volume	312	en_US
utslib.for	0904 Chemical Engineering	en_US
utslib.for	0905 Civil Engineering	en_US
utslib.for	0907 Environmental Engineering	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology/School of Civil and Environmental Engineering
pubs.organisational-group	/University of Technology Sydney/Strength - CTWW - Centre for Technology in Water and Wastewater Treatment
utslib.copyright.status	closed_access
pubs.publication-status	Published	en_US
pubs.volume	312	en_US

Abstract:

© 2016 Elsevier B.V. Biodegradation of β-blocker atenolol was investigated using an enriched nitrifying culture at controlled ammonium concentration and without ammonium addition. Analysis of the kinetics and structural elucidation of biodegradation products showed that atenolol biodegradation was found to be linked to the activity of nitrifying bacteria in the presence of ammonium. Atenolol was degraded cometabolically by ammonia-oxidizing bacteria (AOB), likely due to a broad substrate range of ammonia monooxygenase (AMO). Four products were formed during atenolol biodegradation with ammonia oxidation, including P267 (atenolol acid) and three new products P117 (1-isopropylamino-2-propanol), P167 (1-amino-3-phenoxy-2-propanol), and an unknown product P227 with a nominal molecular mass of 227. In comparison, only P267 and P227 were identified during atenolol biodegradation without ammonia oxidation. Follow-up experiments using atenolol acid as the parent compound indicated the formation of products P117, P167 and P227 in the presence of ammonium. Based on the products identified, a tentative biodegradation pathway of atenolol is suggested, which involves two steps independent of the presence of ammonium: i) microbial amide-bond hydrolysis to carboxyl group and formation of P267 (atenolol acid) and ii) a possible formation of P227 with its unidentified structure and other two cometabolically induced reactions: iii) breakage of ether bond in the alkyl side chain and formation of P117 and iv) a minor pathway through N-dealkylation and loss of acetamide moiety from the aromatic ring, yielding P167. This study provided an important insight regarding the biotransformation pathways under different metabolic conditions.

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http://hdl.handle.net/10453/126661