毛细管电泳法在手性药物分离分析中的应用研究
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摘要
全文共分六个部分,主要内容如下:
第一章前言
毛细管电泳对手性药物分离分析具有独特的优点。本章介绍了毛细管电泳法的拆分机理、毛细管电泳检测方式、分离模式和分离条件的选择。综述了近5年毛细管电泳在手性药物分离分析中的应用,并提出了本论文的研究背景及意义。
第二章毛细管电泳电导法分离与测定盐酸布比卡因注射液中对映体的含量
建立毛细管电泳-电导检测法分离测定盐酸布比卡因注射液中对映体含量的方法。采用熔融石英毛细管柱(60 cm×25μm i.d),以4 mmol/L NH4Ac-4 mmol/L NaAc (以HAc调至pH 4.00)-0.48 mmol/L磺丁基醚-β-环糊精(SBE-β-CD)为运行缓冲液,分离电压12 kV,电动进样3 s。盐酸布比卡因对映体在15 min内得到基线分离,左旋布比卡因在0.1～10.4μg/ml范围内线性关系良好(r=0.9994),检测限为0.052μg/ml。对影响对映体分离的因素,如手性选择剂的类型及浓度、运行缓冲体系的组成及浓度、pH值、分离电压和毛细管内径及长度进行了探讨,并通过计算机辅助分子模拟软件计算药物与不同环糊精的结合能,对盐酸布比卡因与环糊精手性拆分的立体选择性进行了初步的探讨。本法与HPLC法相比,具有高效、快速和经济等优点。
第三章毛细管电泳电导法分离与测定兔血清中盐酸布比卡因对映体的浓度
建立兔血清中盐酸布比卡因对映体的毛细管电泳-电导检测的手性分离方法。兔血清样品碱化后,用三氯甲烷-乙醚(10∶1)提取,以4 mmol/L NH4Ac-4 mmol/L NaAc (以HAc调至pH 4.00)- 0.48mmol/L SBE-β-CD为运行缓冲液,分离电压12 kV,电动进样3 s。盐酸布比卡因对映体在16 min内实现基线分离且不受内源性物质干扰。本试验高效、快速、低耗,适用于盐酸布比卡因对映体体内血药浓度的测定。
第四章毛细管电泳法分离与测定尼群地平和尼莫地平片中对映体的含量
建立毛细管电泳拆分并测定尼群地平片和尼莫地平片中对映体含量的方法。采用熔融石英毛细管柱(62 cm×75μm i.d,有效长度55 cm),以40 mmol/L磷酸二氢钠溶液(以磷酸调至pH 2.96)-10 mmol/L SBE-β-CD为运行缓冲液,分离电压-15 kV,检测波长237 nm。尼群地平和尼莫地平对映体得到基线分离,分离度分别为3.43和2.08。尼群地平和尼莫地平分别在5.016～50.16μg/ml和5.024～50.24μg/ml浓度范围内线性关系良好,检测限分别为2.006μg/ml和2.010μg/ml。尼群地平R和S型对映体的平均回收率分别为95.86%和97.04%,RSD为1.15%和2.06%,尼莫地平R和S型对映体的平均回收率分别为92.76%和97.54%,RSD为2.33%和1.49%。考察了环糊精浓度、缓冲液浓度和pH、分离电压等对分离分析的影响,并运用计算机辅助分子模拟技术对环糊精与对映体间的拆分机理进行初步探讨。
第五章毛细管电泳法分离与测定大鼠血浆中尼群地平和尼莫地平对映体的浓度
建立血浆中尼群地平和尼莫地平对映体的毛细管电泳手性分离分析方法。以对硝基苯甲酸为内标,血浆样品碱化后以乙醚提取2次,运行缓冲液为40 mmol/L磷酸二氢钠溶液(以磷酸调至pH 2.96)-10 mmol/L SBE-β-CD,检测波长为237 nm,尼群地平分离电压为-18 kV,尼莫地平分离电压为-15 kV,电动进样10 s。尼群地平和尼莫地平两对映体均达到基线分离,且不受杂质干扰,尼群地平和尼莫地平分别在28.4~568 ng/ml和27.4~548 ng/ml范围内线性关系良好,检测限分别为11.4 ng/ml和11.0 ng/ml。本方法快速、简单、低耗,适用于尼群地平和尼莫地平在体内立体选择性的研究。
第六章毛细管电泳法分离与测定瑞格列奈片中对映体的含量
建立毛细管电泳分离与测定瑞格列奈片中对映体含量的方法。采用熔融石英毛细管柱(67 cm×75μm i.d,有效长度60 cm),以20 mmol/L Tris(以磷酸调至pH 3.90)-20 mmol/L羟丙基-β-环糊精(HP-β-CD)为运行缓冲液,分离电压20 kV,检测波长243 nm,瑞格列奈对映体实现了基线分离。瑞格列奈在5.00~50.0μg/ml浓度范围内线性关系良好,检测限为0.25μg/ml,S-(+)-瑞格列奈平均回收率为97.15% ,RSD为1.21%。考察了环糊精的类型和浓度、缓冲液的组成和浓度、pH值、分离电压等的影响,并对环糊精与对映体间的拆分机理进行探讨。
This thesis includes the following six chapters:
Chaper 1
Capillary electrophoresis has unique advantages in separation and analysis of chiral drugs. The fundamental principle, chiral recognition mechanism, the choice of separation conditions and separation models of high performance capillary electrophoresis were introduced in this chaper. Applications of CE in chiral drug separation of recent 5 years were reviewed. This part also provided the background and significance of this research.
Chapter 2
Conductivity detection was employed for the detection of the enantiomers of bupivacaine hydrochloride (Bup), which were separated by high performance capillary electrophoresis. Computer-aided technique was used to calculate the binding energies and the interaction between Bup enantiomers and CDs was preliminarily discussed. Factors affecting the separation efficiency such as the types and concentration of chiral selectors, running buffer, pH value, separation voltage and capillary inside diameter and length were studied. Under the optimized condition, a baseline separation of Bup enantiomers was achieved in less than 15 minutes in 4 mmol/L NH4Ac-4 mmol/L NaAc (adjusted to pH 4.00 with acetic acid) -0.48 mmol/L sulfobutyl ether-β-cyclodextrin(SBE-β-CD) running buffer at separation voltage of 12 kV. The lowest detective concentration was 0.052μg/ml. The proposed method was suitable for the chiral separation and quantitative analysis of Bup enantiomers in pharmaceutical injection.
Chapter 3
To establish a HPCE-ECD method for determining the content of enantiomers of bupivacaine hydrochloride in rabbit serum. The running buffer was composed of 4 mmol/L NH4Ac-4 mmol/L NaAc ( adjusted to pH 4.00 with acetic acid) containing 0.48 mmol/L SBE-β-CD, the working voltage was 12 kV. Samples were injected into capillary with a positive voltage of 10 kV for 3 s. The biological samples were alkalized and extracted with chloroform-ethyl ether (10∶1). The enantiomers of bupivacaine hydrochloride were separated at a base line under the above condition in 16 min, and the determination was not interfered by endogenous components from rabbit. This method was high efficient, rapid and low reagent consumption for determining bupivacaine hydrochloride in rabbit serum.
Chapter 4
A high performance capillary electrophoresis method was established for the chiral separation and determination of nitrendipine and nimodipine enantiomers. An uncoated fused sillica capillary column was used with running buffer of 40 mmol/L sodium dihydrogen phosphate (adjusted to pH 2.96 with phosphoric acid)-10 mmol/L SBE-β-CD, at the applied voltage of -15 kV and the detection wavelength of 237 nm. The resolution of enantiomers of nitrendipine and nimodipine were 3.43 and 2.08. The calibration curves of nitrendipine and nimodipine were linear in the concentration ranges of 5.016~50.16μg/ml and 5.024~50.24μg/ml, with the detection limit of 2.006μg/ml and 2.010μg/ml. (R)- nitrendipine and (S)- nitrendipine average recoveries were 95.86% and 97.04%, with RSDs of 1.15% and 2.06%. (R)- nimodipine and (S)- nimodipine average recoveries were 92.76% and 97.54%, with RSDs of 2.33% and 1.49%. Computer-aided technique was used to calculate the binding energies and the factors affecting the separation efficiency such as the concentration of chiral selectors, running buffer, pH value, separation voltage were studied.
Chapter 5
To establish a capillary electrophoresis method for the chiral separation and determination of nitrendipine and nimodipine enantiomers in rats plasma. The biological samples were alkalized and extracted with ethyl ether by twice. The running buffer was composed of 40 mmol/L sodium dihydrogen phosphate(adjusted to pH 2.96 with phosphoric acid)-10 mmol/L SBE-β-CD. The detection wavelength was 237 nm. The applied voltage of nitrendipine and nimodipine enantiomers were -18 kV and -15 kV,respectively. Samples were injected into capillary with electric power for 10 s. p-Nitrobenzoic acid was used as internal standard. Enantiomers of nitrendipine and nimodipine were separated at a base line under the above condition, and the determination was not interfered by endogenous components from rats. The linear concentration range of nitrendipine and nimodipine were 28.4~568 ng/ml and 27.4~548 ng/ml,with the detection limit of 11.4 ng/ml and 11.0 ng/ml.
Chapter 6
A capillary electrophoresis (CE) method with UV detection for the chiral separation and determination of repaglinide enantiomers has been developed. Several parameters such as the composition of the running buffer, the types and concentration of CDs, the pH value, separation voltage, injection time and capillary’s inside diameter and length and sample medium which affect the separation, were investigated to acquire the optimum conditions. Under the optimized condition , a baseline separation of repaglinide enantiomers was achieved in less than 15 minutes in 20 mmol/L Tris(Hydroxymethyl)aminomethane ( adjusted to pH 3.90 with phosphoric acid ) -20 mmol/L Hydroxypropyl-β-cyclodextrin (HP-β-CD)running buffer, at the separation voltage of 20 kV and the detection wavelength of 243 nm. The calibration curve for repaglinide was linear in the concentration range of 5.00~50.00μg/ml with the detection limit of 0.25μg/ml. The average recovery was 97.15%, with RSD of 1.21%. The proposed method was suitable for the separation and quantitative analysis of repaglinide enantiomers in pharmaceutical preparation.
第一章前言
毛细管电泳对手性药物分离分析具有独特的优点。本章介绍了毛细管电泳法的拆分机理、毛细管电泳检测方式、分离模式和分离条件的选择。综述了近5年毛细管电泳在手性药物分离分析中的应用,并提出了本论文的研究背景及意义。
第二章毛细管电泳电导法分离与测定盐酸布比卡因注射液中对映体的含量
建立毛细管电泳-电导检测法分离测定盐酸布比卡因注射液中对映体含量的方法。采用熔融石英毛细管柱(60 cm×25μm i.d),以4 mmol/L NH4Ac-4 mmol/L NaAc (以HAc调至pH 4.00)-0.48 mmol/L磺丁基醚-β-环糊精(SBE-β-CD)为运行缓冲液,分离电压12 kV,电动进样3 s。盐酸布比卡因对映体在15 min内得到基线分离,左旋布比卡因在0.1～10.4μg/ml范围内线性关系良好(r=0.9994),检测限为0.052μg/ml。对影响对映体分离的因素,如手性选择剂的类型及浓度、运行缓冲体系的组成及浓度、pH值、分离电压和毛细管内径及长度进行了探讨,并通过计算机辅助分子模拟软件计算药物与不同环糊精的结合能,对盐酸布比卡因与环糊精手性拆分的立体选择性进行了初步的探讨。本法与HPLC法相比,具有高效、快速和经济等优点。
第三章毛细管电泳电导法分离与测定兔血清中盐酸布比卡因对映体的浓度
建立兔血清中盐酸布比卡因对映体的毛细管电泳-电导检测的手性分离方法。兔血清样品碱化后,用三氯甲烷-乙醚(10∶1)提取,以4 mmol/L NH4Ac-4 mmol/L NaAc (以HAc调至pH 4.00)- 0.48mmol/L SBE-β-CD为运行缓冲液,分离电压12 kV,电动进样3 s。盐酸布比卡因对映体在16 min内实现基线分离且不受内源性物质干扰。本试验高效、快速、低耗,适用于盐酸布比卡因对映体体内血药浓度的测定。
第四章毛细管电泳法分离与测定尼群地平和尼莫地平片中对映体的含量
建立毛细管电泳拆分并测定尼群地平片和尼莫地平片中对映体含量的方法。采用熔融石英毛细管柱(62 cm×75μm i.d,有效长度55 cm),以40 mmol/L磷酸二氢钠溶液(以磷酸调至pH 2.96)-10 mmol/L SBE-β-CD为运行缓冲液,分离电压-15 kV,检测波长237 nm。尼群地平和尼莫地平对映体得到基线分离,分离度分别为3.43和2.08。尼群地平和尼莫地平分别在5.016～50.16μg/ml和5.024～50.24μg/ml浓度范围内线性关系良好,检测限分别为2.006μg/ml和2.010μg/ml。尼群地平R和S型对映体的平均回收率分别为95.86%和97.04%,RSD为1.15%和2.06%,尼莫地平R和S型对映体的平均回收率分别为92.76%和97.54%,RSD为2.33%和1.49%。考察了环糊精浓度、缓冲液浓度和pH、分离电压等对分离分析的影响,并运用计算机辅助分子模拟技术对环糊精与对映体间的拆分机理进行初步探讨。
第五章毛细管电泳法分离与测定大鼠血浆中尼群地平和尼莫地平对映体的浓度
建立血浆中尼群地平和尼莫地平对映体的毛细管电泳手性分离分析方法。以对硝基苯甲酸为内标,血浆样品碱化后以乙醚提取2次,运行缓冲液为40 mmol/L磷酸二氢钠溶液(以磷酸调至pH 2.96)-10 mmol/L SBE-β-CD,检测波长为237 nm,尼群地平分离电压为-18 kV,尼莫地平分离电压为-15 kV,电动进样10 s。尼群地平和尼莫地平两对映体均达到基线分离,且不受杂质干扰,尼群地平和尼莫地平分别在28.4~568 ng/ml和27.4~548 ng/ml范围内线性关系良好,检测限分别为11.4 ng/ml和11.0 ng/ml。本方法快速、简单、低耗,适用于尼群地平和尼莫地平在体内立体选择性的研究。
第六章毛细管电泳法分离与测定瑞格列奈片中对映体的含量
建立毛细管电泳分离与测定瑞格列奈片中对映体含量的方法。采用熔融石英毛细管柱(67 cm×75μm i.d,有效长度60 cm),以20 mmol/L Tris(以磷酸调至pH 3.90)-20 mmol/L羟丙基-β-环糊精(HP-β-CD)为运行缓冲液,分离电压20 kV,检测波长243 nm,瑞格列奈对映体实现了基线分离。瑞格列奈在5.00~50.0μg/ml浓度范围内线性关系良好,检测限为0.25μg/ml,S-(+)-瑞格列奈平均回收率为97.15% ,RSD为1.21%。考察了环糊精的类型和浓度、缓冲液的组成和浓度、pH值、分离电压等的影响,并对环糊精与对映体间的拆分机理进行探讨。
This thesis includes the following six chapters:
Chaper 1
Capillary electrophoresis has unique advantages in separation and analysis of chiral drugs. The fundamental principle, chiral recognition mechanism, the choice of separation conditions and separation models of high performance capillary electrophoresis were introduced in this chaper. Applications of CE in chiral drug separation of recent 5 years were reviewed. This part also provided the background and significance of this research.
Chapter 2
Conductivity detection was employed for the detection of the enantiomers of bupivacaine hydrochloride (Bup), which were separated by high performance capillary electrophoresis. Computer-aided technique was used to calculate the binding energies and the interaction between Bup enantiomers and CDs was preliminarily discussed. Factors affecting the separation efficiency such as the types and concentration of chiral selectors, running buffer, pH value, separation voltage and capillary inside diameter and length were studied. Under the optimized condition, a baseline separation of Bup enantiomers was achieved in less than 15 minutes in 4 mmol/L NH4Ac-4 mmol/L NaAc (adjusted to pH 4.00 with acetic acid) -0.48 mmol/L sulfobutyl ether-β-cyclodextrin(SBE-β-CD) running buffer at separation voltage of 12 kV. The lowest detective concentration was 0.052μg/ml. The proposed method was suitable for the chiral separation and quantitative analysis of Bup enantiomers in pharmaceutical injection.
Chapter 3
To establish a HPCE-ECD method for determining the content of enantiomers of bupivacaine hydrochloride in rabbit serum. The running buffer was composed of 4 mmol/L NH4Ac-4 mmol/L NaAc ( adjusted to pH 4.00 with acetic acid) containing 0.48 mmol/L SBE-β-CD, the working voltage was 12 kV. Samples were injected into capillary with a positive voltage of 10 kV for 3 s. The biological samples were alkalized and extracted with chloroform-ethyl ether (10∶1). The enantiomers of bupivacaine hydrochloride were separated at a base line under the above condition in 16 min, and the determination was not interfered by endogenous components from rabbit. This method was high efficient, rapid and low reagent consumption for determining bupivacaine hydrochloride in rabbit serum.
Chapter 4
A high performance capillary electrophoresis method was established for the chiral separation and determination of nitrendipine and nimodipine enantiomers. An uncoated fused sillica capillary column was used with running buffer of 40 mmol/L sodium dihydrogen phosphate (adjusted to pH 2.96 with phosphoric acid)-10 mmol/L SBE-β-CD, at the applied voltage of -15 kV and the detection wavelength of 237 nm. The resolution of enantiomers of nitrendipine and nimodipine were 3.43 and 2.08. The calibration curves of nitrendipine and nimodipine were linear in the concentration ranges of 5.016~50.16μg/ml and 5.024~50.24μg/ml, with the detection limit of 2.006μg/ml and 2.010μg/ml. (R)- nitrendipine and (S)- nitrendipine average recoveries were 95.86% and 97.04%, with RSDs of 1.15% and 2.06%. (R)- nimodipine and (S)- nimodipine average recoveries were 92.76% and 97.54%, with RSDs of 2.33% and 1.49%. Computer-aided technique was used to calculate the binding energies and the factors affecting the separation efficiency such as the concentration of chiral selectors, running buffer, pH value, separation voltage were studied.
Chapter 5
To establish a capillary electrophoresis method for the chiral separation and determination of nitrendipine and nimodipine enantiomers in rats plasma. The biological samples were alkalized and extracted with ethyl ether by twice. The running buffer was composed of 40 mmol/L sodium dihydrogen phosphate(adjusted to pH 2.96 with phosphoric acid)-10 mmol/L SBE-β-CD. The detection wavelength was 237 nm. The applied voltage of nitrendipine and nimodipine enantiomers were -18 kV and -15 kV,respectively. Samples were injected into capillary with electric power for 10 s. p-Nitrobenzoic acid was used as internal standard. Enantiomers of nitrendipine and nimodipine were separated at a base line under the above condition, and the determination was not interfered by endogenous components from rats. The linear concentration range of nitrendipine and nimodipine were 28.4~568 ng/ml and 27.4~548 ng/ml,with the detection limit of 11.4 ng/ml and 11.0 ng/ml.
Chapter 6
A capillary electrophoresis (CE) method with UV detection for the chiral separation and determination of repaglinide enantiomers has been developed. Several parameters such as the composition of the running buffer, the types and concentration of CDs, the pH value, separation voltage, injection time and capillary’s inside diameter and length and sample medium which affect the separation, were investigated to acquire the optimum conditions. Under the optimized condition , a baseline separation of repaglinide enantiomers was achieved in less than 15 minutes in 20 mmol/L Tris(Hydroxymethyl)aminomethane ( adjusted to pH 3.90 with phosphoric acid ) -20 mmol/L Hydroxypropyl-β-cyclodextrin (HP-β-CD)running buffer, at the separation voltage of 20 kV and the detection wavelength of 243 nm. The calibration curve for repaglinide was linear in the concentration range of 5.00~50.00μg/ml with the detection limit of 0.25μg/ml. The average recovery was 97.15%, with RSD of 1.21%. The proposed method was suitable for the separation and quantitative analysis of repaglinide enantiomers in pharmaceutical preparation.
引文
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