Transformation of tetracyclines mediated by Mn(II) and Cu(II) ions in the presence of oxygen

Wan Ru Chen, Ching Hua Huang

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

Complexation of tetracyclines (TCs) with dissolved Mn II and Cu II ions were found to significantly enhance the transformation of these antibiotics in the presence of oxygen at pH 8-9.5 and pH 4-6, respectively. In the TC-Mn II-O 2 system, oxidation of the TC-complexed Mn II to Mn III by oxygen occurs, followed by oxidation of TC by Mn III to regenerate Mn II. In the TC-Cu II-O 2 system, Cu II oxidizes TC within the complex and the yielded Cu I is reoxidized by the present oxygen. Opposite reactivity trends were observed with the two metals: OTC (oxytetracycline) > TTC (tetracycline) ≫ iso-CTC (isochlorotetracycline) for the Mn II-mediated reaction, whereas CTC > TTC > OTC > epimers for the Cu II-mediated reaction. The reactivity results and examination of TC-metalion complexation and transformation products suggest that the BCD-ring and A-ring of TC are crucial to interact with Mn II and Cu II, respectively. This study highlights thatthe fate of TCs in aquatic environments may differ significantly by their strong interactions with different metal species present in the systems.

Original languageEnglish
Pages (from-to)401-407
Number of pages7
JournalEnvironmental Science and Technology
Volume43
Issue number2
DOIs
Publication statusPublished - 2009 Jan 15

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Tetracyclines
oxytetracycline
Ions
Oxygen
complexation
oxygen
ion
oxidation
metal
antibiotics
aquatic environment
Oxytetracycline
Tetracycline
Complexation
Metals
Oxidation
Anti-Bacterial Agents

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Environmental Chemistry

Cite this

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title = "Transformation of tetracyclines mediated by Mn(II) and Cu(II) ions in the presence of oxygen",
abstract = "Complexation of tetracyclines (TCs) with dissolved Mn II and Cu II ions were found to significantly enhance the transformation of these antibiotics in the presence of oxygen at pH 8-9.5 and pH 4-6, respectively. In the TC-Mn II-O 2 system, oxidation of the TC-complexed Mn II to Mn III by oxygen occurs, followed by oxidation of TC by Mn III to regenerate Mn II. In the TC-Cu II-O 2 system, Cu II oxidizes TC within the complex and the yielded Cu I is reoxidized by the present oxygen. Opposite reactivity trends were observed with the two metals: OTC (oxytetracycline) > TTC (tetracycline) ≫ iso-CTC (isochlorotetracycline) for the Mn II-mediated reaction, whereas CTC > TTC > OTC > epimers for the Cu II-mediated reaction. The reactivity results and examination of TC-metalion complexation and transformation products suggest that the BCD-ring and A-ring of TC are crucial to interact with Mn II and Cu II, respectively. This study highlights thatthe fate of TCs in aquatic environments may differ significantly by their strong interactions with different metal species present in the systems.",
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Transformation of tetracyclines mediated by Mn(II) and Cu(II) ions in the presence of oxygen. / Chen, Wan Ru; Huang, Ching Hua.

In: Environmental Science and Technology, Vol. 43, No. 2, 15.01.2009, p. 401-407.

Research output: Contribution to journalArticle

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N2 - Complexation of tetracyclines (TCs) with dissolved Mn II and Cu II ions were found to significantly enhance the transformation of these antibiotics in the presence of oxygen at pH 8-9.5 and pH 4-6, respectively. In the TC-Mn II-O 2 system, oxidation of the TC-complexed Mn II to Mn III by oxygen occurs, followed by oxidation of TC by Mn III to regenerate Mn II. In the TC-Cu II-O 2 system, Cu II oxidizes TC within the complex and the yielded Cu I is reoxidized by the present oxygen. Opposite reactivity trends were observed with the two metals: OTC (oxytetracycline) > TTC (tetracycline) ≫ iso-CTC (isochlorotetracycline) for the Mn II-mediated reaction, whereas CTC > TTC > OTC > epimers for the Cu II-mediated reaction. The reactivity results and examination of TC-metalion complexation and transformation products suggest that the BCD-ring and A-ring of TC are crucial to interact with Mn II and Cu II, respectively. This study highlights thatthe fate of TCs in aquatic environments may differ significantly by their strong interactions with different metal species present in the systems.

AB - Complexation of tetracyclines (TCs) with dissolved Mn II and Cu II ions were found to significantly enhance the transformation of these antibiotics in the presence of oxygen at pH 8-9.5 and pH 4-6, respectively. In the TC-Mn II-O 2 system, oxidation of the TC-complexed Mn II to Mn III by oxygen occurs, followed by oxidation of TC by Mn III to regenerate Mn II. In the TC-Cu II-O 2 system, Cu II oxidizes TC within the complex and the yielded Cu I is reoxidized by the present oxygen. Opposite reactivity trends were observed with the two metals: OTC (oxytetracycline) > TTC (tetracycline) ≫ iso-CTC (isochlorotetracycline) for the Mn II-mediated reaction, whereas CTC > TTC > OTC > epimers for the Cu II-mediated reaction. The reactivity results and examination of TC-metalion complexation and transformation products suggest that the BCD-ring and A-ring of TC are crucial to interact with Mn II and Cu II, respectively. This study highlights thatthe fate of TCs in aquatic environments may differ significantly by their strong interactions with different metal species present in the systems.

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