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Sonochemical degradation of antibiotics from representative classes- Considerations on structural effects, initial transformation products, antimicrobial activity and matrix
Ultrasonics Sonochemistry ( IF 8.4 ) Pub Date : 2018-09-11 , DOI: 10.1016/j.ultsonch.2018.09.012
Efraím A. Serna-Galvis , Diana Montoya-Rodríguez , Laura Isaza-Pineda , María Ibáñez , Félix Hernández , Alejandro Moncayo-Lasso , Ricardo A. Torres-Palma

In this work, the sonochemical treatment (at 354 kHz and 200W) of six relevant antibiotics belonging to fluoroquinolones (ciprofloxacin and norfloxacin), penicillins (oxacillin and cloxacillin) and cephalosporins (cephalexin and cephadroxyl) classes was evaluated. Firstly, the ability of the process to eliminate them was tested, showing that sonodegradation of these antibiotics is strongly chemical structure-dependent. Thus, correlations among initial degradation rate of pollutants (Rd), solubility in water (Sw), water-octanol partition coefficient (Log P) and topological polar surface area (TPSA) were tested. Rd exhibited a good correlation with Log P (i.e., the hydrophobicity degree of antibiotics). The considered penicillins had the fastest elimination and from the constitutional analysis using Lemke method was clear that the functional groups arrangement on these antibiotics made them highly hydrophobics. The penicillins were degraded closer at cavitation bubble than the fluoroquinolones or cephalosporins. The investigation of degradation products showed that sonogenerated hydroxyl radical primary attacked the β-lactam ring of cloxacillin and cephalexin, whereas on norfloxacin induced a decarboxylation. On the other hand, the evolution of antimicrobial activity was also followed. It was evidenced the process capacity to remove antimicrobial activity from treated solutions, which was associated to the transformations of functional groups on antibiotics with important role for interaction with bacteria. Additionally, degradation of antibiotics having the highest (the most hydrophobic, i.e., cloxacillin) and lowest (the most hydrophilic, i.e., cephadroxyl) Rd, was performed in synthetic matrices (hospital wastewater and seawater). Ultrasound degraded both antibiotics; for cloxacillin in such waters higher eliminations than in distilled water were observed (probably due to a salting-out effect exerted by matrix components). Meanwhile, for cephadroxyl a moderate inhibition of degradation in hospital wastewater and seawater respect to distilled water was found, this was related to competition by hydroxyl radical of the other substances in the matrices. These results show the quite selectivity of high frequency ultrasound to eliminate antibiotics form different classes even in complex matrices.



中文翻译:

代表类别的抗生素的声化学降解-考虑结构效应,初始转化产物,抗菌活性和基质

在这项工作中,对六种相关的抗生素进行了声化学处理(在354 kHz和200W下),这些抗生素分别属于氟喹诺酮类(环丙沙星和诺氟沙星),青霉素(奥沙西林和氯沙西林)和头孢菌素(头孢氨苄和头孢曲氨酰)。首先,测试了消除该过程的能力,表明这些抗生素的超声降解强烈依赖于化学结构。因此,测试了污染物的初始降解率(Rd),在水中的溶解度(Sw),水-辛醇分配系数(Log P)和拓扑极性表面积(TPSA)之间的相关性。Rd表现出与Log P的良好相关性(即抗生素的疏水性程度)。认为的青霉素具有最快的消除效果,并且使用Lemke方法进行的结构分析清楚地表明,这些抗生素上的官能团排列使它们具有高度疏水性。青霉素在空化气泡处的降解比氟喹诺酮类或头孢菌素更接近。降解产物的研究表明,声波产生的羟基自由基主要攻击氯沙西林和头孢氨苄的β-内酰胺环,而诺氟沙星则诱导脱羧。另一方面,还跟踪了抗菌活性的演变。证明了从处理过的溶液中去除抗菌活性的过程能力,这与抗生素上的官能团的转化有关,对与细菌的相互作用具有重要作用。此外,在合成基质(医院废水和海水)中,降解具有最高(最疏水,即氯唑西林)和最低(最亲水,即头孢克罗)Rd的抗生素。超声降解两种抗生素;在这种水中氯吡西林的消除率要高于蒸馏水(可能是由于基质成分产生了盐析作用)。同时,相对于蒸馏水,对于头孢噻吩而言,发现医院废水和海水中的降解受到中等抑制,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。在合成基质(医院废水和海水)中进行最低剂量(氯氧西林)和(最低亲水性,即头孢克洛)Rd的操作。超声降解两种抗生素;在这种水中氯吡西林的消除率要高于蒸馏水(可能是由于基质成分产生了盐析作用)。同时,相对于蒸馏水,对于头孢噻吩而言,发现医院废水和海水中的降解受到中等抑制,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。在合成基质(医院废水和海水)中进行最低剂量(氯氧西林)和(最低亲水性,即头孢克洛)Rd的操作。超声降解两种抗生素;在这种水中氯吡西林的消除率要高于蒸馏水(可能是由于基质成分产生了盐析作用)。同时,相对于蒸馏水,对于头孢噻吩而言,发现医院废水和海水中的降解受到中等抑制,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。超声波降解两种抗生素;在这种水中氯吡西林的消除率要高于蒸馏水(可能是由于基质成分产生了盐析作用)。同时,相对于蒸馏水,对于头孢噻吩而言,发现医院废水和海水中的降解受到中等抑制,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。超声降解两种抗生素;在这种水中氯吡西林的消除率要高于蒸馏水(可能是由于基质成分产生了盐析作用)。同时,相对于蒸馏水,对于头孢噻吩而言,发现医院废水和海水中的降解受到中等抑制,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。对于头孢氨苄,发现与蒸馏水相比,对医院废水和海水的降解具有中等抑制作用,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。对于头孢氨苄,发现与蒸馏水相比,对医院废水和海水的降解具有中等抑制作用,这与基质中其他物质的羟基自由基竞争有关。这些结果表明,即使在复杂的基质中,高频超声也具有很高的选择性,可以消除不同类别的抗生素。

更新日期:2018-09-11
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