TY - JOUR
T1 - Transformation kinetics and pathways of tetracycline antibiotics with manganese oxide
AU - Chen, Wan Ru
AU - Huang, Ching Hua
N1 - Funding Information:
This material is based upon work supported by the National Science Foundation under Grant BES0229172 .
PY - 2011/5
Y1 - 2011/5
N2 - Tetracycline antibiotics including tetracycline (TTC), oxytetracycline (OTC) and chlorotetracycline (CTC) undergo rapid transformation to yield various products in the presence of MnO2 at mild conditions (pH 4-9 and 22 °C). Reaction rates follow the trend of CTC > TTC > OTC, and are affected by pH and complexation of TCs with Mg2+ or Ca2+. Experimental results of TTC indicate that MnO2 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 MnO2 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 MnO2, encompassing transformation patterns observed with both TTC and OTC. The identified product structures suggest lower antibacterial activity than that of the parent tetracyclines.
AB - Tetracycline antibiotics including tetracycline (TTC), oxytetracycline (OTC) and chlorotetracycline (CTC) undergo rapid transformation to yield various products in the presence of MnO2 at mild conditions (pH 4-9 and 22 °C). Reaction rates follow the trend of CTC > TTC > OTC, and are affected by pH and complexation of TCs with Mg2+ or Ca2+. Experimental results of TTC indicate that MnO2 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 MnO2 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 MnO2, encompassing transformation patterns observed with both TTC and OTC. The identified product structures suggest lower antibacterial activity than that of the parent tetracyclines.
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U2 - 10.1016/j.envpol.2011.02.027
DO - 10.1016/j.envpol.2011.02.027
M3 - Article
C2 - 21396756
AN - SCOPUS:79954420472
SN - 0269-7491
VL - 159
SP - 1092
EP - 1100
JO - Environmental Pollution
JF - Environmental Pollution
IS - 5
ER -