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Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide

Abstract

Tetracycline antibiotics including tetracycline (TTC), oxytetracycline (OTC) and chlorotetracycline (CTC) undergo rapid transformation to yield various products in the presence of MnO{sub 2} at mild conditions (pH 4-9 and 22 {sup o}C). Reaction rates follow the trend of CTC > TTC > OTC, and are affected by pH and complexation of TCs with Mg{sup 2+} or Ca{sup 2+}. Experimental results of TTC indicate that MnO{sub 2} promotes isomerization at the C ring to form iso-TTC and oxidizes the phenolic-diketone and tricarbonylamide groups, leading to insertion of up to 2 O most likely at the C9 and C2 positions. In contrast, reactions of OTC with MnO{sub 2} generate little iso-OTC, but occur mainly at the A ring's dimethylamine group to yield N-demethylated products. CTC yields the most complicated products upon reactions with MnO{sub 2}, encompassing transformation patterns observed with both TTC and OTC. The identified product structures suggest lower antibacterial activity than that of the parent tetracyclines. - Highlights: > Tetracyclines transform rapidly by MnO{sub 2} to yield complicated products. > Isomerized, (hydr)oxygenated and N-demethylated products are formed. > Transformation product structures may suggest lowered antibacterial activity. - The complex transformation pathways of three popular tetracycline antibiotics (tetracycline, oxytetracycline and chlorotetracycline)  More>>
Authors:
Wanru, Chen; [1]  Huang, Ching-Hua [1] 
  1. School of Civil and Environmental Engineering, Georgia Institute of Technology, Atlanta, GA 30332 (United States)
Publication Date:
May 15, 2011
Product Type:
Journal Article
Resource Relation:
Journal Name: Environmental Pollution (1987); Journal Volume: 159; Journal Issue: 5; Other Information: DOI: 10.1016/j.envpol.2011.02.027; PII: S0269-7491(11)00101-1; Copyright (c) 2011 Elsevier Science B.V., Amsterdam, The Netherlands, All rights reserved.
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; MANGANESE OXIDES; OXYTETRACYCLINE; REACTION KINETICS; TRANSFORMATIONS; ANTIBIOTICS; ANTI-INFECTIVE AGENTS; CHALCOGENIDES; DRUGS; KINETICS; MANGANESE COMPOUNDS; ORGANIC COMPOUNDS; OXIDES; OXYGEN COMPOUNDS; TETRACYCLINES; TRANSITION ELEMENT COMPOUNDS
OSTI ID:
21543381
Country of Origin:
United Kingdom
Language:
English
Other Identifying Numbers:
Journal ID: ISSN 0269-7491; ENPOEK; TRN: GB11R2437022473
Availability:
Available from http://dx.doi.org/10.1016/j.envpol.2011.02.027
Submitting Site:
GBN
Size:
page(s) 1092-1100
Announcement Date:
Apr 14, 2012

Citation Formats

Wanru, Chen, and Huang, Ching-Hua. Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide. United Kingdom: N. p., 2011. Web. doi:10.1016/j.envpol.2011.02.027.
Wanru, Chen, & Huang, Ching-Hua. Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide. United Kingdom. doi:10.1016/j.envpol.2011.02.027.
Wanru, Chen, and Huang, Ching-Hua. 2011. "Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide." United Kingdom. doi:10.1016/j.envpol.2011.02.027. https://www.osti.gov/servlets/purl/10.1016/j.envpol.2011.02.027.
@misc{etde_21543381,
title = {Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide}
author = {Wanru, Chen, and Huang, Ching-Hua}
abstractNote = {Tetracycline antibiotics including tetracycline (TTC), oxytetracycline (OTC) and chlorotetracycline (CTC) undergo rapid transformation to yield various products in the presence of MnO{sub 2} at mild conditions (pH 4-9 and 22 {sup o}C). Reaction rates follow the trend of CTC > TTC > OTC, and are affected by pH and complexation of TCs with Mg{sup 2+} or Ca{sup 2+}. Experimental results of TTC indicate that MnO{sub 2} promotes isomerization at the C ring to form iso-TTC and oxidizes the phenolic-diketone and tricarbonylamide groups, leading to insertion of up to 2 O most likely at the C9 and C2 positions. In contrast, reactions of OTC with MnO{sub 2} generate little iso-OTC, but occur mainly at the A ring's dimethylamine group to yield N-demethylated products. CTC yields the most complicated products upon reactions with MnO{sub 2}, encompassing transformation patterns observed with both TTC and OTC. The identified product structures suggest lower antibacterial activity than that of the parent tetracyclines. - Highlights: > Tetracyclines transform rapidly by MnO{sub 2} to yield complicated products. > Isomerized, (hydr)oxygenated and N-demethylated products are formed. > Transformation product structures may suggest lowered antibacterial activity. - The complex transformation pathways of three popular tetracycline antibiotics (tetracycline, oxytetracycline and chlorotetracycline) with MnO{sub 2} under environmental conditions are systematically evaluated and elucidated.}
doi = {10.1016/j.envpol.2011.02.027}
journal = {Environmental Pollution (1987)}
issue = {5}
volume = {159}
place = {United Kingdom}
year = {2011}
month = {May}
}