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首页> 外文期刊>Environmental Science & Technology >Ferrate(Ⅵ) Oxidation of β-Lactam Antibiotics: Reaction Kinetics, Antibacterial Activity Changes, and Transformation Products
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Ferrate(Ⅵ) Oxidation of β-Lactam Antibiotics: Reaction Kinetics, Antibacterial Activity Changes, and Transformation Products

机译：高铁酸盐（Ⅵ）氧化β-内酰胺抗生素的反应动力学，抗菌活性变化和转化产物

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摘要

Oxidation of β-lactam antibiotics by aqueous ferrate(Ⅵ) was investigated to determine reaction kinetics, reaction sites, antibacterial activity changes, and transformation products. Apparent second-order rate constants (k_(app)) were determined in the pH range 6.0-93 for the reaction of ferrate(Ⅵ) with penicillins (amoxicillin, ampicillin, cloxacillin, and penicillin G), a cephalosporin (cephalexin), and several model compounds. Ferrate(Ⅵ) shows an appreciable reactivity toward the selected β-lactams (k_(app) for pH 7 = 110-770 M~(-1) s~(-1)). The pH-dependent k_(app) could be well explained by considering species-specific reactions between ferrate(Ⅵ) and the β-lactams (with reactions occurring at thioether, amine, and/or phenol groups). On the basis of the kinetic results, the thioether is the main reaction site for cloxacillin and penicillin G. In addition to the thioether, the amine is a reaction site for ampicillin and cephalexin, and amine and phenol are reaction sites for amoxicillin. HPLC/MS analysis showed that the thioether of β-lactams was transformed to stereoisomeric (R)- and (S)-sulfoxides and then to a sulfone. Quantitative microbiological assay of ferrate(Ⅵ)-treated β-lactam solutions indicated that transformation products resulting from the oxidation of cephalexin exhibited diminished, but non-negligible residual activity (i.e., ～24% as potent as the parent compound). For the other β-lactams, the transformation products showed much lower (＜5%) antibacterial potencies compared to the parent compounds. Overall, ferrate(Ⅵ) oxidation appears to be effective as a means of lowering the antibacterial activities of β-lactams, although alternative approaches may be necessary to achieve complete elimination of cephalosporin activities.
机译：研究了高铁酸盐（Ⅵ）对β-内酰胺类抗生素的氧化反应，确定了反应动力学，反应部位，抗菌活性变化及转化产物。确定高铁酸盐（Ⅵ）与青霉素（阿莫西林，氨苄青霉素，氯西林和青霉素G），头孢菌素（cephalexin）和几种模型化合物。高铁酸盐（Ⅵ）对所选的β-内酰胺具有显着的反应性（pH 7 = 110-770 M〜（-1）s〜（-1）时的k_app）。考虑到高铁酸盐（Ⅵ）和β-内酰胺之间的物种特异性反应（反应发生在硫醚，胺和/或酚基团上），可以很好地解释pH依赖性的k_（app）。根据动力学结果，硫醚是氯沙西林和青霉素G的主要反应位点。除硫醚之外，胺是氨苄青霉素和头孢氨苄的反应位点，胺和苯酚是阿莫西林的反应位点。 HPLC / MS分析表明，β-内酰胺的硫醚转化为（R）-和（S）-亚砜的立体异构体，然后转化为砜。高铁酸盐（Ⅵ）处理过的β-内酰胺溶液的定量微生物学测定表明，由头孢氨苄氧化产生的转化产物虽然减少了，但残留活性却不可忽略（相当于母体化合物的效力约为〜24％）。对于其他β-内酰胺类，转化产物显示出比母体化合物低得多的抗菌力（＜5％）。总的来说，高铁酸盐（Ⅵ）的氧化似乎是降低β-内酰胺类抗菌活性的有效方法，尽管可能需要其他方法来完全消除头孢菌素的活性。

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  • 来源
    《Environmental Science & Technology》 |2014年第17期|10380-10389|共10页
  • 作者

    Anggita Karlesa; Glen Andrew D. De Vera; Michael C. Dodd; Jihye Park; Maria Pythias B. Espino; Yunho Lee;

  • 作者单位

    Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 500-712, Republic of Korea;

    Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 500-712, Republic of Korea, Institute of Chemistry, College of Science, University of the Philippines, Diliman, Quezon City 1101, Philippines;

    Department of Civil and Environmental Engineering, University of Washington, Seattle, Washington 98195, United States;

    Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 500-712, Republic of Korea;

    Institute of Chemistry, College of Science, University of the Philippines, Diliman, Quezon City 1101, Philippines;

    Department of Environmental Science and Engineering, Gwangju Institute of Science and Technology (GIST), Gwangju, 500-712, Republic of Korea;

  • 收录信息 美国《科学引文索引》(SCI);美国《工程索引》(EI);美国《生物学医学文摘》(MEDLINE);美国《化学文摘》(CA);
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