青霉素类抗生素荧光分析方法的研究
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摘要
青霉素类抗生素因其廉价、高效等特点广泛应用于医学和兽医学临床治疗及饲料添加剂,然而人们在抗生素使用过程中存在不规范、滥用行为,引起动物源食品中药物的残留,给人类的健康和生态环境带来了危害。因此,建立一类灵敏、可靠、简便的青霉素类抗生素检测方法就显得尤为重要。本文主要研究了青霉素类抗生素中常见的三种药物苄青霉素、阿莫西林、氨苄西林的荧光分析法,主要的研究内容如下：
一、NBD-Cl荧光衍生化法测定苄青霉素的研究
采用荧光光谱法研究了荧光衍生试剂4-氯-7-硝基-2,1,3-苯并氧杂恶二唑(NBD-Cl)与苄青霉素降解产物的衍生化反应。结果表明NBD-Cl与苄青霉素的酸性降解产物在弱碱性的水溶液中易发生反应,生成稳定的荧光络合物,从而使得不具有荧光的苄青霉素显示荧光性质,据此建立一种测定苄青霉素的荧光新方法。在最佳条件下,苄青霉素浓度在0.1-20.0 mg/L范围内与荧光强度呈良好的线性关系,检出限为20μg/L。同时研究了络合物的缔合常数,探讨了衍生化反应的自由能变化及机理。利用该方法对牛奶中苄青霉素含量进行了测定,相对标准偏差为1.32%-2.13%,并进行了标准加入回收试验,其回收率为88.4%-95.2%。
二、荷移荧光光谱法测定青霉素类抗生素的研究
1.荷移荧光光谱法测定苄青霉素的研究
采用荧光光谱法研究了电子供体苄青霉素降解产物与电子接受体四氯苯醌(TCBQ)之间的荷移反应,结果表明TCBQ与苄青霉素的酸性降解产物在甲醇-水介质中易发生荷移反应,生成稳定的络合物,其荧光强度较苄青霉素降解产物本身有了显著的增强。据此建立一种测定苄青霉素的新方法,在最佳条件下,苄青霉素浓度在0.30～8.0 mg/L范围内与荧光强度呈良好的线性关系,检出限为90μg/L。同时研究了荷移络合物的红外光谱,探讨了荷移反应的机理。利用该方法对牛奶中苄青霉素含量进行了测定,并进行了标准加入回收试验,回收率为88.0%-95.4%,相对标准偏差为1.12%-1.46%。
2.p-环糊精增敏荷移荧光光谱法测定氨苄西林与阿莫西林
研究了电子供体氨苄西林(AMP)、阿莫西林(AMO)与电子接受体7,7,8,8-四氰基苯醌二甲烷(TCNQ)之间的荷移反应,建立了测定AMP和AMO的新荧光光谱法。结果表明：AMP、AMO与TCNQ于45℃下可生成n-π络合物,使其荧光强度较药物本身得到增强。在此基础上,通过β-环糊精(p-CD)的包合作用,体系的灵敏度和稳定性得到进一步增强。在最佳条件下,AMP、AMO的浓度分别在0.1～10.0mg/L、0.05～6.0 mg/L范围内与荧光强度呈良好的线性关系,检出限分别为30μg/L、10μg/L。同时研究了荷移络合物的缔合常数,探讨了荷移反应的自由能变化及机理。利用该方法对胶囊制剂中的AMP和AMO含量进行测定,并进行标准加入回收试验,其回收率分别为102.3%和98.2%。此方法灵敏、简便、准确,结果与药典方法相一致。
三、荧光散射光谱法测定青霉素类抗生素的研究
在pH 4-5的HCl溶液和加热条件下,青霉素类抗生素(PENs)如氨苄西林(AMP)、阿莫西林(AMO)、苄青霉素(BEN)可水解成中间产物与Cu(Ⅱ)反应形成1：1的二元螯合物PENs-Cu(Ⅱ),它们能一进步与碘三负离子(Ⅰ3-)反应生成1：1：1的三元离子缔合物PENs-Cu(Ⅱ)-I3-。结果引起了溶液的共振瑞利散射(RRS)和非线性散射如二级散射(SOS)、倍频散射(FDS)的显著增强。在一定范围内,抗生素的浓度与增加的散射强度成线性关系。三种青霉素类抗生素AMP、AMO、BEN的检出限(3σ)分别是32μg/L、95μg/L、151μg/L (RRS方法),177μ.g/L、102μg/L、184μg/L (SOS方法),85μg/L、68μg/L、138μg/L (FDS方法),RRS法测定AMP体系是所研究检测方法中灵敏度最高的。本文以RRS方法为例研究了反应体系的最佳条件实验和影响因素,探讨了离子缔合物组成比和反应的机理。测试了外来共存物质的影响,结果表明该方法具有较好的选择性。以离子缔合反应为基础,本文建立起一种灵敏、简便、快速的检测青霉素类抗生素的新方法。该法可应用于测定胶囊制剂、牛奶、人体尿液样品中的青霉素类抗生素。
Penicillin antibiotics are widely used in clinical medicine, veterinary medicine and feed additives due to their low-cost and efficient peculiarities. However, the irregular and abusive use of antibiotics will lead to drug residues in animal-derived food and finally do harm to human health and entironment. Therefore, it is significant to develop a series of sensitive, reliable and convenient methods for the determination of penicillin antibiotics. In this paper, fluorescence analysis of common penicillins antibiotics, such as benzylpenicillin (BEN), amoxicillin (AMO) and ampicillin (AMP) have been studied. The main contents are as follows:
Part 1 Study on the fluorescence spectrometric determination of benzylpenicillin by derivatization reaction with NBD-C1
The derivatization reaction of 4-Chloro-7-nitro-2,1,3-benzoxadiazole (NBD-C1) as fluorescence derivatizing agent with benzylpenicillin degradation was investigated by fluorimetry. The results showed that NBD-C1 was prone to react with acidic degradation products of benzylpenicillin to produce stable fluorescent complexes in weak alkaline solution. Thereby the fluorescence property of benzylpenicillin was displayed. A new method for the fluorescence determination of benzylpenicillin has been developed. A linear calibration graph was obtained over the benzylpenicillin concentration range from 0.1～20.0 mg/L with a detection limit of 20μg/L under optimal conditions. Furthermore, the association constant of derivative complex was studied. Standard free energy changes and the mechanism of derivatization reaction were explored. The method has been applied to the determination of benzylpenicillin in milk and the relative standard deviation was 1.32%～2.13%. Spiked recovery tests were also carried out and the recoveries were 88.4%～95.2%.
Part 2 Study on the fluorescence spectrometric for the determination of penicillins antibiotics by charge-transfer reaction
Chapter 1 Study on the fluorescence spectrometric for the determination of benzylpenicillin by charge-transfer reaction
The charge-transfer reaction of benzylpenicillin degradation as the donor with 2,3,5,6-tetrachloro-1,4-benzoquinone (TCBQ) as the acceptor was investigated by fluorimetry. The results showed that TCBQ was prone to react with acidic degradation products of benzylpenicillin to produce stable charge-transfer complexes in a mixture of methanol and water. Fluorescence intensity of the complex was increased significantly relative to benzylpenicillin degradation. Therefore a new method for the determination of benzylpenicillin has been developed. A linear calibration graph was obtained over the benzylpenicillin concentration range from 0.30-8.0 mg/L with a detection limit of 90μg/L under optimal conditions. Furthermore, infrared spectroscopy of charge-transfer complex was studied and the mechanism of charge-transfer reaction was explored. The method has been applied to the determination of benzylpenicillin in milk and spiked recovery tests were carried out. The recoveries were 88.0%-95.4%, and the relative standard deviation was 1.12%～1.46%.
Chapter 2β-cyclodextrin enhanced fluorimetric method for the determination of ampicillin and amoxicillin by charge-transfer reaction
The charge-transfer reaction of ampicillin (AMP) and amoxicillin (AMO) as the donor with 7,7,8,8-tetracyanoquinodimethane (TCNQ) as the acceptor was investigated. A new fluorimetric method for the determination of AMP and AMO was developed. The results showed that TCNQ was prone to react with both AMP and AMO to produce n-πcomplexes at 45℃. The fluorescence intensity of the complex was enhanced significantly relative to that of the studied drugs itself. On the basis, the sensitivity and stability of system were further enhanced due to the clathration ofβ-cyclodextrin (β-CD). The linear calibration graphs were obtained over the AMP, AMO concentration range from 0.1～10.0, 0.05～6.0 mg/L with a detection limit of 30μg/L,10μg/L, respectively. Furthermore, the association constants of charge-transfer complex were studied. Standard free energy changes and the mechanism of charge-transfer reaction were explored. The method has been applied to determine the content of AMP and AMO in capsule and spiked recovery tests were carried out. The recoveries were 102.3% and 98.2% for AMP and AMO, respectively. This method is sensitive, easy and accurate, the results are in good agreement with those obtained with the Chinese Pharmacopoeia method.
Part 3 Study on the fluorescence scattering spectrometric for the determination of penicillins antibiotics
Under pH 4-5 HC1 solution and heating condition, penicillins antibiotics (PENs) such as ampicillin (AMP), amoxicillin (AMO) and benzylpenicillin (BEN) were hydrolyzed into intermediates to react with copper(Ⅱ) (Cu(Ⅱ)) to form 1:1 binary chelates (PENs-Cu(Ⅱ)), which can further react with triiodide (I3-) to form 1:1:1 ternary ion-association complexes (PENs-Cu(Ⅱ)-I3-). As a result, the resonance Rayleigh scattering (RRS) and non-linear scattering such as second-order scattering (SOS) and frequency doubling scattering (FDS) were enhanced greatly. The increments of scattering intensity (ΔI) were directly proportional to the concentrations of the antibiotics in certain ranges. The detection limits (3σ) of the three PENs for AMP, AMO and BEN systems were 32μg/L,95μg/L and 151μg/L (RRS method),177μg/L,102μg/L and 184μg/L (SOS method) and 85μg/L,68μg/L and 138μg/L (FDS method), respectively. AMP system for RRS method was the most sensitive. RRS method was taken as an example for the studies of the optimum conditions and influence factors.the composition of ion-association complexes and the reaction mechanism were discussed. The effects of foreign substances were tested and it showed that the method has a good selectivity. Based on the ion-association reaction, a new sensitive, simple and rapid method for the determination of penicillin antibiotics has been developed. It can be applied to the determination of penicillin antibiotics in capsule, milk and human urine samples.
一、NBD-Cl荧光衍生化法测定苄青霉素的研究
采用荧光光谱法研究了荧光衍生试剂4-氯-7-硝基-2,1,3-苯并氧杂恶二唑(NBD-Cl)与苄青霉素降解产物的衍生化反应。结果表明NBD-Cl与苄青霉素的酸性降解产物在弱碱性的水溶液中易发生反应,生成稳定的荧光络合物,从而使得不具有荧光的苄青霉素显示荧光性质,据此建立一种测定苄青霉素的荧光新方法。在最佳条件下,苄青霉素浓度在0.1-20.0 mg/L范围内与荧光强度呈良好的线性关系,检出限为20μg/L。同时研究了络合物的缔合常数,探讨了衍生化反应的自由能变化及机理。利用该方法对牛奶中苄青霉素含量进行了测定,相对标准偏差为1.32%-2.13%,并进行了标准加入回收试验,其回收率为88.4%-95.2%。
二、荷移荧光光谱法测定青霉素类抗生素的研究
1.荷移荧光光谱法测定苄青霉素的研究
采用荧光光谱法研究了电子供体苄青霉素降解产物与电子接受体四氯苯醌(TCBQ)之间的荷移反应,结果表明TCBQ与苄青霉素的酸性降解产物在甲醇-水介质中易发生荷移反应,生成稳定的络合物,其荧光强度较苄青霉素降解产物本身有了显著的增强。据此建立一种测定苄青霉素的新方法,在最佳条件下,苄青霉素浓度在0.30～8.0 mg/L范围内与荧光强度呈良好的线性关系,检出限为90μg/L。同时研究了荷移络合物的红外光谱,探讨了荷移反应的机理。利用该方法对牛奶中苄青霉素含量进行了测定,并进行了标准加入回收试验,回收率为88.0%-95.4%,相对标准偏差为1.12%-1.46%。
2.p-环糊精增敏荷移荧光光谱法测定氨苄西林与阿莫西林
研究了电子供体氨苄西林(AMP)、阿莫西林(AMO)与电子接受体7,7,8,8-四氰基苯醌二甲烷(TCNQ)之间的荷移反应,建立了测定AMP和AMO的新荧光光谱法。结果表明：AMP、AMO与TCNQ于45℃下可生成n-π络合物,使其荧光强度较药物本身得到增强。在此基础上,通过β-环糊精(p-CD)的包合作用,体系的灵敏度和稳定性得到进一步增强。在最佳条件下,AMP、AMO的浓度分别在0.1～10.0mg/L、0.05～6.0 mg/L范围内与荧光强度呈良好的线性关系,检出限分别为30μg/L、10μg/L。同时研究了荷移络合物的缔合常数,探讨了荷移反应的自由能变化及机理。利用该方法对胶囊制剂中的AMP和AMO含量进行测定,并进行标准加入回收试验,其回收率分别为102.3%和98.2%。此方法灵敏、简便、准确,结果与药典方法相一致。
三、荧光散射光谱法测定青霉素类抗生素的研究
在pH 4-5的HCl溶液和加热条件下,青霉素类抗生素(PENs)如氨苄西林(AMP)、阿莫西林(AMO)、苄青霉素(BEN)可水解成中间产物与Cu(Ⅱ)反应形成1：1的二元螯合物PENs-Cu(Ⅱ),它们能一进步与碘三负离子(Ⅰ3-)反应生成1：1：1的三元离子缔合物PENs-Cu(Ⅱ)-I3-。结果引起了溶液的共振瑞利散射(RRS)和非线性散射如二级散射(SOS)、倍频散射(FDS)的显著增强。在一定范围内,抗生素的浓度与增加的散射强度成线性关系。三种青霉素类抗生素AMP、AMO、BEN的检出限(3σ)分别是32μg/L、95μg/L、151μg/L (RRS方法),177μ.g/L、102μg/L、184μg/L (SOS方法),85μg/L、68μg/L、138μg/L (FDS方法),RRS法测定AMP体系是所研究检测方法中灵敏度最高的。本文以RRS方法为例研究了反应体系的最佳条件实验和影响因素,探讨了离子缔合物组成比和反应的机理。测试了外来共存物质的影响,结果表明该方法具有较好的选择性。以离子缔合反应为基础,本文建立起一种灵敏、简便、快速的检测青霉素类抗生素的新方法。该法可应用于测定胶囊制剂、牛奶、人体尿液样品中的青霉素类抗生素。
Penicillin antibiotics are widely used in clinical medicine, veterinary medicine and feed additives due to their low-cost and efficient peculiarities. However, the irregular and abusive use of antibiotics will lead to drug residues in animal-derived food and finally do harm to human health and entironment. Therefore, it is significant to develop a series of sensitive, reliable and convenient methods for the determination of penicillin antibiotics. In this paper, fluorescence analysis of common penicillins antibiotics, such as benzylpenicillin (BEN), amoxicillin (AMO) and ampicillin (AMP) have been studied. The main contents are as follows:
Part 1 Study on the fluorescence spectrometric determination of benzylpenicillin by derivatization reaction with NBD-C1
The derivatization reaction of 4-Chloro-7-nitro-2,1,3-benzoxadiazole (NBD-C1) as fluorescence derivatizing agent with benzylpenicillin degradation was investigated by fluorimetry. The results showed that NBD-C1 was prone to react with acidic degradation products of benzylpenicillin to produce stable fluorescent complexes in weak alkaline solution. Thereby the fluorescence property of benzylpenicillin was displayed. A new method for the fluorescence determination of benzylpenicillin has been developed. A linear calibration graph was obtained over the benzylpenicillin concentration range from 0.1～20.0 mg/L with a detection limit of 20μg/L under optimal conditions. Furthermore, the association constant of derivative complex was studied. Standard free energy changes and the mechanism of derivatization reaction were explored. The method has been applied to the determination of benzylpenicillin in milk and the relative standard deviation was 1.32%～2.13%. Spiked recovery tests were also carried out and the recoveries were 88.4%～95.2%.
Part 2 Study on the fluorescence spectrometric for the determination of penicillins antibiotics by charge-transfer reaction
Chapter 1 Study on the fluorescence spectrometric for the determination of benzylpenicillin by charge-transfer reaction
The charge-transfer reaction of benzylpenicillin degradation as the donor with 2,3,5,6-tetrachloro-1,4-benzoquinone (TCBQ) as the acceptor was investigated by fluorimetry. The results showed that TCBQ was prone to react with acidic degradation products of benzylpenicillin to produce stable charge-transfer complexes in a mixture of methanol and water. Fluorescence intensity of the complex was increased significantly relative to benzylpenicillin degradation. Therefore a new method for the determination of benzylpenicillin has been developed. A linear calibration graph was obtained over the benzylpenicillin concentration range from 0.30-8.0 mg/L with a detection limit of 90μg/L under optimal conditions. Furthermore, infrared spectroscopy of charge-transfer complex was studied and the mechanism of charge-transfer reaction was explored. The method has been applied to the determination of benzylpenicillin in milk and spiked recovery tests were carried out. The recoveries were 88.0%-95.4%, and the relative standard deviation was 1.12%～1.46%.
Chapter 2β-cyclodextrin enhanced fluorimetric method for the determination of ampicillin and amoxicillin by charge-transfer reaction
The charge-transfer reaction of ampicillin (AMP) and amoxicillin (AMO) as the donor with 7,7,8,8-tetracyanoquinodimethane (TCNQ) as the acceptor was investigated. A new fluorimetric method for the determination of AMP and AMO was developed. The results showed that TCNQ was prone to react with both AMP and AMO to produce n-πcomplexes at 45℃. The fluorescence intensity of the complex was enhanced significantly relative to that of the studied drugs itself. On the basis, the sensitivity and stability of system were further enhanced due to the clathration ofβ-cyclodextrin (β-CD). The linear calibration graphs were obtained over the AMP, AMO concentration range from 0.1～10.0, 0.05～6.0 mg/L with a detection limit of 30μg/L,10μg/L, respectively. Furthermore, the association constants of charge-transfer complex were studied. Standard free energy changes and the mechanism of charge-transfer reaction were explored. The method has been applied to determine the content of AMP and AMO in capsule and spiked recovery tests were carried out. The recoveries were 102.3% and 98.2% for AMP and AMO, respectively. This method is sensitive, easy and accurate, the results are in good agreement with those obtained with the Chinese Pharmacopoeia method.
Part 3 Study on the fluorescence scattering spectrometric for the determination of penicillins antibiotics
Under pH 4-5 HC1 solution and heating condition, penicillins antibiotics (PENs) such as ampicillin (AMP), amoxicillin (AMO) and benzylpenicillin (BEN) were hydrolyzed into intermediates to react with copper(Ⅱ) (Cu(Ⅱ)) to form 1:1 binary chelates (PENs-Cu(Ⅱ)), which can further react with triiodide (I3-) to form 1:1:1 ternary ion-association complexes (PENs-Cu(Ⅱ)-I3-). As a result, the resonance Rayleigh scattering (RRS) and non-linear scattering such as second-order scattering (SOS) and frequency doubling scattering (FDS) were enhanced greatly. The increments of scattering intensity (ΔI) were directly proportional to the concentrations of the antibiotics in certain ranges. The detection limits (3σ) of the three PENs for AMP, AMO and BEN systems were 32μg/L,95μg/L and 151μg/L (RRS method),177μg/L,102μg/L and 184μg/L (SOS method) and 85μg/L,68μg/L and 138μg/L (FDS method), respectively. AMP system for RRS method was the most sensitive. RRS method was taken as an example for the studies of the optimum conditions and influence factors.the composition of ion-association complexes and the reaction mechanism were discussed. The effects of foreign substances were tested and it showed that the method has a good selectivity. Based on the ion-association reaction, a new sensitive, simple and rapid method for the determination of penicillin antibiotics has been developed. It can be applied to the determination of penicillin antibiotics in capsule, milk and human urine samples.
引文
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