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description Publicationkeyboard_double_arrow_right Article , Other literature type 2013 Italy, NetherlandsPublisher:American Society for Microbiology Funded by:SNSF | Investigating the degrada..., EC | MINOTAURUSSNSF| Investigating the degradation of sulfonamides in Microbacterium sp. strain BR1 - is ipso-substitution involved? ,EC| MINOTAURUSBenjamin Ricken; Philippe F.-X. Corvini; Danuta Cichocka; Martina Parisi; Markus Lenz; Dominik Wyss; Paula M. Martínez-Lavanchy; Jochen A. Müller; Patrick Shahgaldian; Ludovico G. Tulli; Hans-Peter E. Kohler; Boris A. Kolvenbach;ABSTRACT Sulfonamide antibiotics have a wide application range in human and veterinary medicine. Because they tend to persist in the environment, they pose potential problems with regard to the propagation of antibiotic resistance. Here, we identified metabolites formed during the degradation of sulfamethoxazole and other sulfonamides in Microbacterium sp. strain BR1. Our experiments showed that the degradation proceeded along an unusual pathway initiated by ipso -hydroxylation with subsequent fragmentation of the parent compound. The NADH-dependent hydroxylation of the carbon atom attached to the sulfonyl group resulted in the release of sulfite, 3-amino-5-methylisoxazole, and benzoquinone-imine. The latter was concomitantly transformed to 4-aminophenol. Sulfadiazine, sulfamethizole, sulfamethazine, sulfadimethoxine, 4-amino- N -phenylbenzenesulfonamide, and N -(4-aminophenyl)sulfonylcarbamic acid methyl ester (asulam) were transformed accordingly. Therefore, ipso -hydroxylation with subsequent fragmentation must be considered the underlying mechanism; this could also occur in the same or in a similar way in other studies, where biotransformation of sulfonamides bearing an amino group in the para -position to the sulfonyl substituent was observed to yield products corresponding to the stable metabolites observed by us.
Europe PubMed Centra... arrow_drop_down Applied and Environmental Microbiology; Research@WURArticle . 2013 . Peer-reviewedLicense: ASM Journals Non-Commercial TDMApplied and Environmental Microbiology; Archivio istituzionale della ricerca - Alma Mater Studiorum Università di BolognaOther literature type . Article . 2013 . Peer-reviewedadd ClaimPlease grant OpenAIRE to access and update your ORCID works.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.All Research productsarrow_drop_down <script type="text/javascript"> <!-- document.write('<div id="oa_widget"></div>'); document.write('<script type="text/javascript" src="https://www.openaire.eu/index.php?option=com_openaire&view=widget&format=raw&projectId=10.1128/aem.00911-13&type=result"></script>'); --> </script>
For further information contact us at helpdesk@openaire.euAccess RoutesGreen bronze 87 citations 87 popularity Top 10% influence Top 10% impulse Top 10% Powered by BIP!more_vert Europe PubMed Centra... arrow_drop_down Applied and Environmental Microbiology; Research@WURArticle . 2013 . Peer-reviewedLicense: ASM Journals Non-Commercial TDMApplied and Environmental Microbiology; Archivio istituzionale della ricerca - Alma Mater Studiorum Università di BolognaOther literature type . Article . 2013 . Peer-reviewedadd ClaimPlease grant OpenAIRE to access and update your ORCID works.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.All Research productsarrow_drop_down <script type="text/javascript"> <!-- document.write('<div id="oa_widget"></div>'); document.write('<script type="text/javascript" src="https://www.openaire.eu/index.php?option=com_openaire&view=widget&format=raw&projectId=10.1128/aem.00911-13&type=result"></script>'); --> </script>
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description Publicationkeyboard_double_arrow_right Article , Other literature type 2013 Italy, NetherlandsPublisher:American Society for Microbiology Funded by:SNSF | Investigating the degrada..., EC | MINOTAURUSSNSF| Investigating the degradation of sulfonamides in Microbacterium sp. strain BR1 - is ipso-substitution involved? ,EC| MINOTAURUSBenjamin Ricken; Philippe F.-X. Corvini; Danuta Cichocka; Martina Parisi; Markus Lenz; Dominik Wyss; Paula M. Martínez-Lavanchy; Jochen A. Müller; Patrick Shahgaldian; Ludovico G. Tulli; Hans-Peter E. Kohler; Boris A. Kolvenbach;ABSTRACT Sulfonamide antibiotics have a wide application range in human and veterinary medicine. Because they tend to persist in the environment, they pose potential problems with regard to the propagation of antibiotic resistance. Here, we identified metabolites formed during the degradation of sulfamethoxazole and other sulfonamides in Microbacterium sp. strain BR1. Our experiments showed that the degradation proceeded along an unusual pathway initiated by ipso -hydroxylation with subsequent fragmentation of the parent compound. The NADH-dependent hydroxylation of the carbon atom attached to the sulfonyl group resulted in the release of sulfite, 3-amino-5-methylisoxazole, and benzoquinone-imine. The latter was concomitantly transformed to 4-aminophenol. Sulfadiazine, sulfamethizole, sulfamethazine, sulfadimethoxine, 4-amino- N -phenylbenzenesulfonamide, and N -(4-aminophenyl)sulfonylcarbamic acid methyl ester (asulam) were transformed accordingly. Therefore, ipso -hydroxylation with subsequent fragmentation must be considered the underlying mechanism; this could also occur in the same or in a similar way in other studies, where biotransformation of sulfonamides bearing an amino group in the para -position to the sulfonyl substituent was observed to yield products corresponding to the stable metabolites observed by us.
Europe PubMed Centra... arrow_drop_down Applied and Environmental Microbiology; Research@WURArticle . 2013 . Peer-reviewedLicense: ASM Journals Non-Commercial TDMApplied and Environmental Microbiology; Archivio istituzionale della ricerca - Alma Mater Studiorum Università di BolognaOther literature type . Article . 2013 . Peer-reviewedadd ClaimPlease grant OpenAIRE to access and update your ORCID works.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.All Research productsarrow_drop_down <script type="text/javascript"> <!-- document.write('<div id="oa_widget"></div>'); document.write('<script type="text/javascript" src="https://www.openaire.eu/index.php?option=com_openaire&view=widget&format=raw&projectId=10.1128/aem.00911-13&type=result"></script>'); --> </script>
For further information contact us at helpdesk@openaire.euAccess RoutesGreen bronze 87 citations 87 popularity Top 10% influence Top 10% impulse Top 10% Powered by BIP!more_vert Europe PubMed Centra... arrow_drop_down Applied and Environmental Microbiology; Research@WURArticle . 2013 . Peer-reviewedLicense: ASM Journals Non-Commercial TDMApplied and Environmental Microbiology; Archivio istituzionale della ricerca - Alma Mater Studiorum Università di BolognaOther literature type . Article . 2013 . Peer-reviewedadd ClaimPlease grant OpenAIRE to access and update your ORCID works.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.This Research product is the result of merged Research products in OpenAIRE.
You have already added works in your ORCID record related to the merged Research product.All Research productsarrow_drop_down <script type="text/javascript"> <!-- document.write('<div id="oa_widget"></div>'); document.write('<script type="text/javascript" src="https://www.openaire.eu/index.php?option=com_openaire&view=widget&format=raw&projectId=10.1128/aem.00911-13&type=result"></script>'); --> </script>
For further information contact us at helpdesk@openaire.eu