高效液相色谱—化学发光分析研究
摘要
化学发光(chemiluminescence,CL)是在没有光、电、磁、声、热源激发的情况下,由化学反应或生物化学反应产生的一种光辐射。以此为基础的化学发光分析,由于可以进行发射光子计量,又没有外来激发光源存在时散射光背景的干扰,因而具有很高的灵敏度(检出限可达10~(-12)-10~(-21)mol),很宽的线性范围(3-6个数量级),同时仪器设备又很简单、廉价、易微型化,在近三十年发展非常迅速。然而,化学发光分析法的一个突出的缺点是选择性比较差,严重制约了它的应用。人们采用了多种方法来弥补化学发光分析的这个缺陷,一是与特异性分子识别反应联用,如酶反应,包括纯酶反应、动植物组织或细胞:抗原-抗体反应或受体-配体反应:核酸、适配体、DNA、RNA等特异性识别及分子印迹聚合物识别等。另一种方法是将化学发光分析同高效分离方法相结合,如高效液相色谱、毛细管电泳和凝胶电泳等。
高效液相色谱(High Performance Liquid Chromatography,HPLC)是一种具有高效、快速及应用广泛的现代分离技术,具有分离效率高、选择性好、分析速度快、操作自动化、应用范围广的特点,已经成为有机物质分析的支柱技术,在生物化学、临床医学、食品检验、石油化工及环境污染监测等领域得到广泛的应用。对HPLC的研究主要集中在三个方面:一是研究各种类型的色谱柱;二是研究与HPLC耦合的检测器:三是研究如何拓宽HPLC的应用范围。检测器作为HPLC系统的重要组成部分,充当着“眼睛”的角色。人们已经研究和开发了多种检测器,如紫外-可见光检测器(UV-VIS)、光电二极管阵列检测器(PDA)、荧光检测器(FLD)、示差折光检测器(RID)、电化学检测器(ECD)、蒸发激光散射检测器(ELSD)、光电导检测器(PCD)、磁旋光检测器(MDR)、放射性检测器(RD)、热离子化检测器(TlD)、化学发光检测器(CLD)和质谱(MS)检测器等。在众多的HPLC捡测器当中.化学发光检测器结构简单,背景低,灵敏度高,被越来越多地应用于各种复杂样品中Pg或龟级含量化合物的检测。与紫外检测器、荧光检测器等常用的检测器不同,化学发光检测器不是一种通用的检测器,某些共存物质即使不能通过色谱柱很好分离,也会因为其中一些物质不能发生化学发光,或者产生化学发光的条件不同而被区分开来,这就可以避免了在紫外检测等方法里不可避免的干扰。因此化学发光检测器与HPLC联用成为当今化学发光分析分析研究及应用非常活跃的热点之一。
HPLC-CL联用技术从理论上结合了二者的优势,可以实现高灵敏度、高选择性的快速分离分析,实际应用中仍然存在两个主要问题:1)由于化学发光检测器需要在检测池中进行化学发光反应,反应试剂溶液的加入会出现稀释效应并导致色谱峰展宽,使HPLC分离度降低。2)色谱分离条件与化学发光反应条件不一致,因而不是所有的化学发光体系都适合用作色谱柱后检测器。
围绕这两个问题,本研究设计了一种新的化学发光检测池,将分离柱后的毛细导管直接插入流动的和不断更新的化学发光试剂环形池中,由于所建立的化学发光反应是一种快速化学发光反应。从柱后流出的各分离组分能立即在检测池中产生化学发光反应并立刻被窗口检测到。这样设计的检测池无任何死体积和稀释效应存在,与传统的化学发光检测器比较,获得的色谱峰比较窄,从而提高了分离度。通过在完成反应池设计、柱后接口、优化色谱分离和化学发光检测器条件的基础上,提出了一系列灵敏度高、选择性好的HPLC-CL检测新方法,并将这些新的高效液相色谱-化学发光检测方法应用于生物样品如人体血液和尿液中某些痕量药物的检测。结合微透析技术还实现了活体、在线、实时药物代谢动力学研究。
活体动态生化分析是近年来在分析化学领域迅速发展起来的新的研究领域,其中微透析技术占重要地位。微透析技术是一种新型的生物采样技术,在药物代谢动力学领域,尤其是在药物分布与代谢的研究方面发挥着日益重要的作用。传统的药代动力学研究都是采用脱线分析,不能完全真实反应组分在动物体内的分布和代谢情况。而微透析取样方法对组织损伤小,可以在基本上不破坏生物体内环境的前提下对细胞间液中小分子物质进行连续取样。当采用在线分析时,还可以使被透析出的物质在接近体内环境的条件下得到检测,可以实时的监测到体内多种化合物量随时间的变化。取样无需匀浆过程,可真实代表取样位点目标化合物的浓度,同时在体内不同部位插入微透析探针可研究目标化合物的体内分布,即具有空间分辨性。这是其它化学微环境在位监测方法无法比拟的,对于研究生命过程、进行疾病诊断以及开展约物研究具有重要意义。本论文还研究了HPLC-CL分折方法与微透析采样技术结合起来的活体动态生化分析,并应用于药物和生化物质的动力学代谢研究。
现就HPLC-CL检测技术的研究进展(第一章)和具体研究工作(第二-四章)简述如下:
第一章主要就HPLC-CL检测技术的基本原理、典型化学发光反应体系(包括鲁米诺及其衍生物、过氧化草酸酯、三(2,2-联吡啶)钌(Ⅱ)、高锰酸钾化学发光体系等)、柱后化学发光检测器的构建及近10年来在生命科学、药学、临床医学、环境及食品等领域的应用和进展情况进行了评述。对这一检测技术在实际应用中存在的问题进行了分析,对其发展方向进行了展望。
第二章就luminol-K_3Fe(CN)_3化学发光检测方法与高效液相色谱分离技术的结合及其在儿茶酚胺类药物分析中应用进行了研究,主要包括:
1、微透析采样,高效液相色谱分离和鲁米诺-铁氰化钾化学发光活体在线检测血液中左旋多巴:
基于左旋多巴可以增强鲁米诺-铁氰化钾化学发光信号的现象,结合高效液相色谱,建立了新的HPLC-CL左旋多巴分析方法。而微透析技术是一种新的采样技术,它具有活体、原位采样,实时、在线检测等突出特点。本研究设计了微透析探针系统,又将这个新的采样技术与HPLC-CL联用,实现了家兔血液中的左旋多巴活体在线检测。灌流液以5μl/min的速度灌流,将血液中的分析物透析出来,经HPLC分离后用CL检测。该方法获得的响应信号在1×10~(-8)-1×10~(-6)g/mL(r~2=0.9995)浓度范围内呈良好的线性关系,检出限为3×10~(-9)g/mL(3σ)。获得的药时曲线表明左旋多巴的血药浓度在服药90分钟时达到最高值,与药典上分析结果一致。
2、HPLC-鲁米诺-铁氰化钾化学发光检测同时测定人血清中的肾上腺素、去甲肾上腺素和多巴胺:
肾上腺素、去甲肾上腺素和多巴胺对鲁米诺-铁氰化钾化学发光体系都有增敏作用,可以分别用本化学发光体系进行检测。但是它们三者在同一个系统中,则会产生相互干扰。本研究设计反应池、优化色谱分离条件,建立了这三种物质同时测定的HPLC-CL新方法。以0.01mol/L邻苯二甲酸氢钾溶液-甲醇(92/8,v/v)为流动相在C_(18)反相色谱柱上实现分离,柱后用CL进行检测。在优化好的各项条件下,肾上腺素、去甲肾上腺素和多巴胺的线性范围分别是1×10~(-8)-5×10~(-6),5.0×10~(-9)-1.0×10~(-6)和5.0×10~(-9)-1.0×10~(-6)g/mL。检出限分别为4.0×10~(-9),1.0×10~(-9)和8.0×10~(-10)g/mL。该方法已成功用于血清样品中三种物质的分析,加标回收率在97-106.7%之间。
第三章研究了高锰酸钾-甲醛化学发光体系在高效液相色谱柱后检测技术的应用,包括:
3、高锰酸钾-甲醛化学发光法高效液相色谱柱后检测血清中的肌苷
本文采用高效液相色谱与化学发光检测联用法,用酸性高锰酸钾和甲醛作为发光剂,流动注射化学发光来测定肌苷,用55:45的甲醇:水作为流动相,肌苷的质量浓度在0.4-12μgmL~(-1),范围内与化学发光强度呈良好的线性关系。其检出限为0.15μg mL~(-1),测定的相对标准偏差为2.9%,(c=1.0×10~(-6)g/mL,n=9)。该方法已成功地用于测定人体血清中的肌苷。
4、高锰酸钾-甲醛化学发光法高效液相色谱柱后检测血清中的维生素B_6
本文基于酸性介质中甲醛会增敏高锰酸钾化学发光体系,建立了一个新的高锰酸钾-甲醛-维生素B_6化学发光体系,并将其与高分离效率的HPLC耦合,克服了化学发光选择性差的缺陷,在优化好的条件下,维生素B_6对该体系的化学发光响应线性范围为0.3-10μg mL~(-1),检出限为0.1μg mL~(-1),测定的相对标准偏差为3.7%,(c=1.0×10~(-6)g/mL,n=7)。该方法已成功地用于同时测定人血清中的维生素B_6。
5、高锰酸钾-甲醛化学发光法高效液相色谱柱后检测尿样中的异丙嗪
高锰酸钾实际常用的化学发光试剂,经研究发现在酸性介质中可以氧化盐酸异丙嗪产生化学发光。而甲醛可以增敏高锰酸钾-异丙嗪化学发光。基于这样的原理,建立了HPLC-CL检测盐酸异丙嗪的新方法。在实验优化的最佳条件下盐酸异丙嗪的质量浓度在1-100μg mL~(-1)范围内与化学发光强度呈良好的线性关系,其线性方程为△I=16.9234+26.3620c(r~2=0.9993),对1μg mL~(-1)的盐酸异丙嗪平行测定11次,其相对标准偏差为2.7%。根据IUPAC建议计算得本方法的检出限为3×10~(-7) g mL~(-1)。
第四章研究了联吡啶钌-Ce(Ⅳ)化学发光体系在高效液相色谱柱后检测技术,包括:
6、联吡啶钌-Ce(Ⅳ)化学发光体系检测血清和尿样中的呋噻米
Ce(Ⅳ)为氧化剂时,一方面与呋噻米发生氧化还原反应生成活性中间体,另一方面又将Ru(bipy)_3~(2+)氧化成Ru(bipy)_3~(3+)。后者与呋噻米活性中间体发生反应产生激发态Ru(bipy)_3~(2+*),然后释放出光能回到基态,并且产生的化学发光强度与呋噻米浓度在一定范围内呈线性关系。本文基于这样的反应体系,建立了Ce(Ⅳ)-Ru(bry)_3~(2+)-呋噻米化学发光分析方法,并将这个高灵敏的CL分析方法与高分离效率的HPLC耦合起来,在设计反应池的基础上,形成一个新的灵敏、快速的呋噻米分析方法,检出限为3.0×10~(-8)g/mL,线性范围在1-50×10~(-7)g/mL,并成功用于血清样品中呋噻米的测定。
7、联吡啶钌-Ce(Ⅳ)化学发光体系检测片剂和血清中的己烯雌酚
本文研究发现酸性介质中Ce(Ⅳ)可以同时氧化DES和Ru(bipy)_3~(2+),两个氧化还原反应生成的中间产物再相互作用生成激发态Ru(bipy)_3~(2+*),激发态Ru(bipy)_3~(2+*)通过释放光能回到基态,由此产生化学发光,且化学发光强度与DES浓度在一定范围内呈线性关系。基于此,本文建立了新的测定DES的CL方法,并设计了反应池,使之与HPLC耦合后,尽量减少柱后峰展宽,保持化学发光方法的灵敏度,同时优化了各项分析分离条件和化学发光反应条件,利用HPLC的高分辨效率,成功实现了血清等复杂生物样品中DES的分析,在8×10~(-8)-1×10~(-5)g/mL范围内成良好的线性关系,方法检出限为3.0×10~(-8)g/mL。对8×10~(-7)g/mL的己烯雌酚连续进行7次平行测定的相对标准偏差为3.6%。
8、联吡啶钌-Ce(Ⅳ)化学发光体系检测血清和尿样中的甲磺酸酚妥拉明
本文研究发现,酸性介质中,酚妥拉明被Ce(Ⅳ)氧化生成活性中间体。有Ru(bipy)_3~(2+)存在时,Ru(bipy)_3~(2+)同时也被Ce(Ⅳ)氧化成+3价Ru(bipy)_3~(2+)。酚妥拉明活性中间体接着与Ru(bipy)_3~(3+)产生反应生成激发态Ru(bipy)_3~(2+*),激发态Ru(bipy)_3~(2+*)通过释放光能回到基态,由此产生化学发光,且化学发光强度与酚妥拉明浓度在一定范围内呈线性关系。基于此,在完成反应池设计基础上,首次提出用HPLC-CL联用技术测定生物样品中的酚妥拉明,对4×10~(-7)g/mL的酚妥拉明连续进行11次平行测定的相对标准偏差为3.1%,方法检出限为3.0×10~(-8)g/mL。在1～20×10~(-7)g/mL范围内线性方程为△I=-55.95+46.40c(r~2=0.9985),效果令人满意。
Chemiluminescence is a light emission from chemical reactions.Chemiluminescence analysis has some advantages such as high sensitivity,wide linear range and simple instrument. It has become an attractive analytical tool in biological and chemical analysis.However,the CL analysis has also some disadvantage;the main disadvantage is very poor selectivity which limited its application widely.How to solute this problem?
One of the approaches is combining the CL analysis with high performance separation method such as the high performance liquid cheromatograpy or capillary elecrophorecence.The another approach is combining with specific molecular recognation such as enzyme reaction including pure enzyme,plant and animal tissue or cell,antibody,antigen or receptor,nucleic acid,aptamer,DNA or RNA and molecular imprinting polymer.
As a powerful modern separation technique,High Performance Liquid Chromatography (HPLC) has been widely used for the analysis of many analytes in diverse fields.Detectors are one of the most important components of HPLC system since they produce a wealth of information about the separated components which can be stored in computers and manipulated as desired to assist solute identification.In recent years,chemiluminescence(CL) as a detection technique of HPLC is very attractive due to higher sensitivity,wider linear dynamic ranges and simpler instrumentation.The advance of CL detection has greatly catalyzed the growth and popularity of HPLC-CL application,and made trace analysis possible owing to its capability of measuring pictogram or femtogram quantities of compounds in the column eluate.The investigations and applications of HPLC-CL technology are currently also an important subject, and a hot point in analytical science.The combination of HPLC separation,which is versatile and robust,and CL-based reactions,which are extremely sensitive,is promising for numerous applications in recent years.
However,the number of the practical CL methods so far reported are not so many owing to some limitation as follows:in HPLC-CL methods,the reagent such as oxidizing reagent is delivered for the post-column CL reaction using additional pump.Thus,the dilution of the analytes by mixing with reagent sometimes results in the lower sensitivity.So far the CL reagents used in HPLC are still limited,the complicated chemistry involved makes application of these reagents in HPLC even more difficult.Although many types of reactors(interfaces) have been developed;however,most of them are still in the optimization phase and mainly suited to the fast kinetic reaction.In addition,analysis of real samples in HPLC-CL is unsatisfactory probably due to matrix interference.
To solve these problems,we designed a simple reactor so extraordinary that it can obtain the most luminescent intensity as soon as the CL reaction was carried out.Moreover,there wasn't any dead volume and dilution effect.The new assemble technique based on HPLC coupled with CL detection has been successfully applied in determination of some medicinements or neurotransmitters.The effects of several parameters on the HPLC resolution and CL emission were studied systematically.Several novel methods based on HPLC with chemiluminescence detectetor have been developed for the determination of in pharmaceutical and biological samples.Coupled with microdialysis,one of the HPLC-CL systems has been applied to study the pharmacokinetics of some drugs for in-vivo,on-line and real time determination.
Microdialysis sampling has become a powerful technique for studying biochemical events in the extraceilular fluid of actually any tissue,organ or biological fluid in recent years.It is a standard technique in the neurosciences and has been extended to use in many other fields including pharmacokinetic,bioprocess monitoring etc.Microdialysis is a dynamic sampling method based on analyte diffusion across a semipermeable membrane driven by a concentration gradient.The advantage of using microdialysis sampling is that relatively low numbers of experimental animals can be used and the physiological and anatomical features of their tissue remain intact during sampling with the microdialysis probe.In addition, microdialysis sampling coupled with appropriate analytical chemical technology can be applied to continuously monitor chemical changes within the ECF with respect to time at one implantation site.Microdialysis has also the advantage that the technique is easy to automate and can be on-line coupled with many analytical techniques.On-line HPLC with microdialysis perfusion provides simplified sample preparation and automated analyses.
In this research work,we have developed a new HPLC-analysis-CL method and successfully applied it to monitor levodopa in rabbit blood in vivo and on-line.
This dissertation consists of four chapters.Chapters 1 is a review and Chapters 2 to 4 are research reports including 8 research works.
In Chapter 1,the development and tendency of the HPLC with CL detection are reviewed. It covers the principles of the HPLC with CL detector,the design of CL detectors,CL detection systems(including luminol,peroxyoxalates,Ru(bipy) 3~(2+),KMnO_4),the applications of analytical methods for many kinds of inorganic,organic and biologic samples,and the trends of HPLC-CL in environmental,life science,pharmacy and clinical medical science.
The research works includes:
(1) High Performance Liquid Chromatography-Chemiluminescence Detection for the in vivo on-line determination and study of the pharmacokinetics of Levodopa in blood with microdialysis sampling
A simple,reliable and reproducible method for in vivo on-line separation and determination of ievodopa based on high performance liquid chromatography with chemiluminescence detection and microdialysis is described.The perfusate is perfused at a flow rate of 5μL/min. The concentration of levodopa in the dialysate is determined on line with a chemiluminescence system.The dialysate sample volume is about 20μL.The system is linearly related to the concentration of levodopa in the range 1×10~(-8)-1×10~(-6)g/mL(r~2 =0.9995) with a detection l imit(3σ) of 3×10~(-9) g/mL and the sample throughput of 12h~(-1),RSD is 2.8%(n=11).The method has been successfully applied to study the pharmacokinetics of levodopa in vivo,and the C_(max),AUC_(0-t) and T_(max) value of the pharmacokinetics parameter are 16.60ng/mL,20.92ng/mL,90min respectively.
(2) Simultaneous determination of Epinephrine,Noradrenaline and Dopamine in human serum samples by high performance liquid chromatography with chemiluminescence detection
A simple,rapid and accurate high performance liquid chromatographic(HPLC) technique coupled with chemiluminescence(CL) detection was developed for the simultaneous determination of epinephrine(E),noradrenaline(NA) and dopamine(DA).It was based on the analyte enhancement effect on the CL reaction between luminol and potassium ferricyanide.The effects of various parameters,such as potassium ferricyanide concentration,luminol concentration,pH value and component of the mobile phase on chromatographic behaviors of the analytes(E,NA and DA) were investigated.The separation was carried out on C_(18) column using the mobile phase of 0.01 mol/L potassium hydrogen phthalate solution and methanol(92:8,ν/ν).Under the optimum conditions,E,NA and DA showed good linear relationships in the range of 1×10~(-8)-5×10~(-6),5.0×10~(-9)-1.0×10~(-6) and 5.0×10~(-9)-1.0×10~(-6)g/mL respectively.The detection limits for E,NA and DA were 4.0×10~(-9),1.0×10~(-9) and 8.0×10~(-10)g/mL.The proposed method has been applied successfully to the analysis of E,NA and DA in human serum samples.
(3) Determination of Inosine in human serum using high-performance liquid chromatography with chemiluminescence detection
Based on the sensitizing effect of formaldehyde on the chemiluminescence(CL) reaction of Inosine with acidic potassium permanganate and the combination technique of high-performance liquid chromatography(HPLC),a sensitive,selective and simple post-column CL detection method for determining Inosine is described.The optimal conditions for the CL detection and HPLC separation were carried out.The linear range is 0.4-12μg mL~(-1) for Inosine.The detection limit of is 0.1μg mL~(-1) and the relative standard deviation with a concentration of 0.15×10~(-6) g/mL was 2.9%respectively(n=9).The method has been satisfactorily applied to the determination of lnosine in pharmaceutical preparations and human serum samples
(4) High Performance Liquid Chromatography-Chemiluminescence Detection for Vitamin B6 in human serum
This paper described a sensitive,selective and simple post-column CL detection method for determining VB_6.It was based on the sensitizing effect of formaldehyde on the chemiluminescence(CL) reaction of VB_6 with acidic potassium permanganate and the combination technique of high-performance liquid chromatography(HPLC).The optimal conditions for the CL detection and HPLC separation were carried out.The linear range is 0.3-10μg mL~(-1) for VB6,the detection limit of is 0.1μgmL~(-1) and the relative standard deviation with a concentrati on of 1.0×10~(-6) g/mL was 3.7%for VB_6(n=7).The method has been satisfactorily applied to the determination of VB_6 in pharmaceutical preparations and human serum samples
(5) Determination of Promethazine Hydrochioride in human urine using high-performance liquid chromatography with chemiluminescence detection
A sensitive,selective and simple post-column CL detection method for determining Promethazine Hydrochloride is described based on the sensitizing effect of formaldehyde on the chemiluminescence(CL) reaction of Promethazine Hydrochloride with acidic potassium permanganate and the combination technique of high-performance liquid chromatography (HPLC),The optimal conditions for the CL detection and HPLC separation were carried out.The linear range is 1--100μg mL~(-1) for Promethazine Hydrochloride,the detection limit of is 0.3μgmL~(-1) and the relative standard deviation with a concentration of 1.0×10~(-6) g/mL was 2.7% for Promethazine Hydrochloride(n=11).The method has been satisfactorily applied to the determination ofPromethazine Hydroehloride in human urine samples
(6) Chemiluminescent detection of fruoside in serum and urine samples after HPLC separation
A novel method was developed for the determination of fruoside by high-performance liquid chromatography(HPLC) coupled with chemiluminescence(CL) detection.The separation was carried out with an isocratic elution using the mobile phase of 50:49:1(ν/ν/ν) water-methanol -phosphate buffer(containing 7.0×10~(-4)M Potassium dihydrogen phosphate,pH 3.0) at a flow rate of 1.1 mL/min.The CL intensity was linear within the range of 1～50×10~(-7)g/mL to the fruoside's concentration,and the detection limits at a signal-to-noise of 3 was 3.0×10~(-8)g/mL.The method was successfully applied to the determination of fruoside in serum and urine samples.The possible mechanism of the CL reaction was also discussed briefly.
(7)Development of a HPLC-chemiluminescence assay for diethylstilbestrol(DES) in tablets and serum samples
A new,highly sensitive chemiluminescence method for measurement of diethylstilbestrol (DES) in various substances such as human serum and tablets has been developed.The method is based on reverse-phase high performance liquid chromatographic separation and subsequent tris(2,2'-bipyridine)ruthenium(Ⅱ)-Ce(Ⅳ) chemiluminescence detection.It was confirmed that DES show strong chemiluminescence upon mixing with tris(2,2′-bipyridine) ruthenium(Ⅱ)-Ce(Ⅳ). A calibration graph,based on a standard DES solution,was linear over the range 8×10~(-8)～1×10~(-5)g/mL and the detection limit was 3.0×10~(-8)g/mL(signal-to-noise ratio=3).This highly sensitive and selective determination method can be applied to selected samples without purification or pre-concentration procedures.The proposed method is easier,more sensitive,and time-saving.
(8)Analysis of phentolamine by HPLC with Ru(bipy)_3Cl_2-Ce(Ⅳ) chemiluminescence detection
A simple,selective and sensitive method for the determination of phentolamine has been developed using high-performance liquid chromatography with chemiluminescence detection. The phentolamine were separated on a C_(18) reversed-phase column with an isocratic elution using the mobile phase of 50:49:1(ν/ν/ν) water-methanol-phosphate buffer(containing 7.0×10~(-4)M Potassium dihydrophosphate,pH 3.0) at a flow rate of 0.8mL/min.The eluate was mixed with tris(2,2′-bipyridyl)ruthenium(Ⅱ)-Ce(Ⅳ),and the generated chemiluminescence was detected. Calibration graphs,based on standard solutions,were linear over the range 1～20×10~(-7)g/mL.The detection limits at a signal-to-noise ratio of 3 ranged 3.0×10~(-8)g/mL.The relative standard deviations was 3.1%.This HPLC system was successfully applied to the determination of phentolamine in serum and urine samples.
高效液相色谱(High Performance Liquid Chromatography,HPLC)是一种具有高效、快速及应用广泛的现代分离技术,具有分离效率高、选择性好、分析速度快、操作自动化、应用范围广的特点,已经成为有机物质分析的支柱技术,在生物化学、临床医学、食品检验、石油化工及环境污染监测等领域得到广泛的应用。对HPLC的研究主要集中在三个方面:一是研究各种类型的色谱柱;二是研究与HPLC耦合的检测器:三是研究如何拓宽HPLC的应用范围。检测器作为HPLC系统的重要组成部分,充当着“眼睛”的角色。人们已经研究和开发了多种检测器,如紫外-可见光检测器(UV-VIS)、光电二极管阵列检测器(PDA)、荧光检测器(FLD)、示差折光检测器(RID)、电化学检测器(ECD)、蒸发激光散射检测器(ELSD)、光电导检测器(PCD)、磁旋光检测器(MDR)、放射性检测器(RD)、热离子化检测器(TlD)、化学发光检测器(CLD)和质谱(MS)检测器等。在众多的HPLC捡测器当中.化学发光检测器结构简单,背景低,灵敏度高,被越来越多地应用于各种复杂样品中Pg或龟级含量化合物的检测。与紫外检测器、荧光检测器等常用的检测器不同,化学发光检测器不是一种通用的检测器,某些共存物质即使不能通过色谱柱很好分离,也会因为其中一些物质不能发生化学发光,或者产生化学发光的条件不同而被区分开来,这就可以避免了在紫外检测等方法里不可避免的干扰。因此化学发光检测器与HPLC联用成为当今化学发光分析分析研究及应用非常活跃的热点之一。
HPLC-CL联用技术从理论上结合了二者的优势,可以实现高灵敏度、高选择性的快速分离分析,实际应用中仍然存在两个主要问题:1)由于化学发光检测器需要在检测池中进行化学发光反应,反应试剂溶液的加入会出现稀释效应并导致色谱峰展宽,使HPLC分离度降低。2)色谱分离条件与化学发光反应条件不一致,因而不是所有的化学发光体系都适合用作色谱柱后检测器。
围绕这两个问题,本研究设计了一种新的化学发光检测池,将分离柱后的毛细导管直接插入流动的和不断更新的化学发光试剂环形池中,由于所建立的化学发光反应是一种快速化学发光反应。从柱后流出的各分离组分能立即在检测池中产生化学发光反应并立刻被窗口检测到。这样设计的检测池无任何死体积和稀释效应存在,与传统的化学发光检测器比较,获得的色谱峰比较窄,从而提高了分离度。通过在完成反应池设计、柱后接口、优化色谱分离和化学发光检测器条件的基础上,提出了一系列灵敏度高、选择性好的HPLC-CL检测新方法,并将这些新的高效液相色谱-化学发光检测方法应用于生物样品如人体血液和尿液中某些痕量药物的检测。结合微透析技术还实现了活体、在线、实时药物代谢动力学研究。
活体动态生化分析是近年来在分析化学领域迅速发展起来的新的研究领域,其中微透析技术占重要地位。微透析技术是一种新型的生物采样技术,在药物代谢动力学领域,尤其是在药物分布与代谢的研究方面发挥着日益重要的作用。传统的药代动力学研究都是采用脱线分析,不能完全真实反应组分在动物体内的分布和代谢情况。而微透析取样方法对组织损伤小,可以在基本上不破坏生物体内环境的前提下对细胞间液中小分子物质进行连续取样。当采用在线分析时,还可以使被透析出的物质在接近体内环境的条件下得到检测,可以实时的监测到体内多种化合物量随时间的变化。取样无需匀浆过程,可真实代表取样位点目标化合物的浓度,同时在体内不同部位插入微透析探针可研究目标化合物的体内分布,即具有空间分辨性。这是其它化学微环境在位监测方法无法比拟的,对于研究生命过程、进行疾病诊断以及开展约物研究具有重要意义。本论文还研究了HPLC-CL分折方法与微透析采样技术结合起来的活体动态生化分析,并应用于药物和生化物质的动力学代谢研究。
现就HPLC-CL检测技术的研究进展(第一章)和具体研究工作(第二-四章)简述如下:
第一章主要就HPLC-CL检测技术的基本原理、典型化学发光反应体系(包括鲁米诺及其衍生物、过氧化草酸酯、三(2,2-联吡啶)钌(Ⅱ)、高锰酸钾化学发光体系等)、柱后化学发光检测器的构建及近10年来在生命科学、药学、临床医学、环境及食品等领域的应用和进展情况进行了评述。对这一检测技术在实际应用中存在的问题进行了分析,对其发展方向进行了展望。
第二章就luminol-K_3Fe(CN)_3化学发光检测方法与高效液相色谱分离技术的结合及其在儿茶酚胺类药物分析中应用进行了研究,主要包括:
1、微透析采样,高效液相色谱分离和鲁米诺-铁氰化钾化学发光活体在线检测血液中左旋多巴:
基于左旋多巴可以增强鲁米诺-铁氰化钾化学发光信号的现象,结合高效液相色谱,建立了新的HPLC-CL左旋多巴分析方法。而微透析技术是一种新的采样技术,它具有活体、原位采样,实时、在线检测等突出特点。本研究设计了微透析探针系统,又将这个新的采样技术与HPLC-CL联用,实现了家兔血液中的左旋多巴活体在线检测。灌流液以5μl/min的速度灌流,将血液中的分析物透析出来,经HPLC分离后用CL检测。该方法获得的响应信号在1×10~(-8)-1×10~(-6)g/mL(r~2=0.9995)浓度范围内呈良好的线性关系,检出限为3×10~(-9)g/mL(3σ)。获得的药时曲线表明左旋多巴的血药浓度在服药90分钟时达到最高值,与药典上分析结果一致。
2、HPLC-鲁米诺-铁氰化钾化学发光检测同时测定人血清中的肾上腺素、去甲肾上腺素和多巴胺:
肾上腺素、去甲肾上腺素和多巴胺对鲁米诺-铁氰化钾化学发光体系都有增敏作用,可以分别用本化学发光体系进行检测。但是它们三者在同一个系统中,则会产生相互干扰。本研究设计反应池、优化色谱分离条件,建立了这三种物质同时测定的HPLC-CL新方法。以0.01mol/L邻苯二甲酸氢钾溶液-甲醇(92/8,v/v)为流动相在C_(18)反相色谱柱上实现分离,柱后用CL进行检测。在优化好的各项条件下,肾上腺素、去甲肾上腺素和多巴胺的线性范围分别是1×10~(-8)-5×10~(-6),5.0×10~(-9)-1.0×10~(-6)和5.0×10~(-9)-1.0×10~(-6)g/mL。检出限分别为4.0×10~(-9),1.0×10~(-9)和8.0×10~(-10)g/mL。该方法已成功用于血清样品中三种物质的分析,加标回收率在97-106.7%之间。
第三章研究了高锰酸钾-甲醛化学发光体系在高效液相色谱柱后检测技术的应用,包括:
3、高锰酸钾-甲醛化学发光法高效液相色谱柱后检测血清中的肌苷
本文采用高效液相色谱与化学发光检测联用法,用酸性高锰酸钾和甲醛作为发光剂,流动注射化学发光来测定肌苷,用55:45的甲醇:水作为流动相,肌苷的质量浓度在0.4-12μgmL~(-1),范围内与化学发光强度呈良好的线性关系。其检出限为0.15μg mL~(-1),测定的相对标准偏差为2.9%,(c=1.0×10~(-6)g/mL,n=9)。该方法已成功地用于测定人体血清中的肌苷。
4、高锰酸钾-甲醛化学发光法高效液相色谱柱后检测血清中的维生素B_6
本文基于酸性介质中甲醛会增敏高锰酸钾化学发光体系,建立了一个新的高锰酸钾-甲醛-维生素B_6化学发光体系,并将其与高分离效率的HPLC耦合,克服了化学发光选择性差的缺陷,在优化好的条件下,维生素B_6对该体系的化学发光响应线性范围为0.3-10μg mL~(-1),检出限为0.1μg mL~(-1),测定的相对标准偏差为3.7%,(c=1.0×10~(-6)g/mL,n=7)。该方法已成功地用于同时测定人血清中的维生素B_6。
5、高锰酸钾-甲醛化学发光法高效液相色谱柱后检测尿样中的异丙嗪
高锰酸钾实际常用的化学发光试剂,经研究发现在酸性介质中可以氧化盐酸异丙嗪产生化学发光。而甲醛可以增敏高锰酸钾-异丙嗪化学发光。基于这样的原理,建立了HPLC-CL检测盐酸异丙嗪的新方法。在实验优化的最佳条件下盐酸异丙嗪的质量浓度在1-100μg mL~(-1)范围内与化学发光强度呈良好的线性关系,其线性方程为△I=16.9234+26.3620c(r~2=0.9993),对1μg mL~(-1)的盐酸异丙嗪平行测定11次,其相对标准偏差为2.7%。根据IUPAC建议计算得本方法的检出限为3×10~(-7) g mL~(-1)。
第四章研究了联吡啶钌-Ce(Ⅳ)化学发光体系在高效液相色谱柱后检测技术,包括:
6、联吡啶钌-Ce(Ⅳ)化学发光体系检测血清和尿样中的呋噻米
Ce(Ⅳ)为氧化剂时,一方面与呋噻米发生氧化还原反应生成活性中间体,另一方面又将Ru(bipy)_3~(2+)氧化成Ru(bipy)_3~(3+)。后者与呋噻米活性中间体发生反应产生激发态Ru(bipy)_3~(2+*),然后释放出光能回到基态,并且产生的化学发光强度与呋噻米浓度在一定范围内呈线性关系。本文基于这样的反应体系,建立了Ce(Ⅳ)-Ru(bry)_3~(2+)-呋噻米化学发光分析方法,并将这个高灵敏的CL分析方法与高分离效率的HPLC耦合起来,在设计反应池的基础上,形成一个新的灵敏、快速的呋噻米分析方法,检出限为3.0×10~(-8)g/mL,线性范围在1-50×10~(-7)g/mL,并成功用于血清样品中呋噻米的测定。
7、联吡啶钌-Ce(Ⅳ)化学发光体系检测片剂和血清中的己烯雌酚
本文研究发现酸性介质中Ce(Ⅳ)可以同时氧化DES和Ru(bipy)_3~(2+),两个氧化还原反应生成的中间产物再相互作用生成激发态Ru(bipy)_3~(2+*),激发态Ru(bipy)_3~(2+*)通过释放光能回到基态,由此产生化学发光,且化学发光强度与DES浓度在一定范围内呈线性关系。基于此,本文建立了新的测定DES的CL方法,并设计了反应池,使之与HPLC耦合后,尽量减少柱后峰展宽,保持化学发光方法的灵敏度,同时优化了各项分析分离条件和化学发光反应条件,利用HPLC的高分辨效率,成功实现了血清等复杂生物样品中DES的分析,在8×10~(-8)-1×10~(-5)g/mL范围内成良好的线性关系,方法检出限为3.0×10~(-8)g/mL。对8×10~(-7)g/mL的己烯雌酚连续进行7次平行测定的相对标准偏差为3.6%。
8、联吡啶钌-Ce(Ⅳ)化学发光体系检测血清和尿样中的甲磺酸酚妥拉明
本文研究发现,酸性介质中,酚妥拉明被Ce(Ⅳ)氧化生成活性中间体。有Ru(bipy)_3~(2+)存在时,Ru(bipy)_3~(2+)同时也被Ce(Ⅳ)氧化成+3价Ru(bipy)_3~(2+)。酚妥拉明活性中间体接着与Ru(bipy)_3~(3+)产生反应生成激发态Ru(bipy)_3~(2+*),激发态Ru(bipy)_3~(2+*)通过释放光能回到基态,由此产生化学发光,且化学发光强度与酚妥拉明浓度在一定范围内呈线性关系。基于此,在完成反应池设计基础上,首次提出用HPLC-CL联用技术测定生物样品中的酚妥拉明,对4×10~(-7)g/mL的酚妥拉明连续进行11次平行测定的相对标准偏差为3.1%,方法检出限为3.0×10~(-8)g/mL。在1～20×10~(-7)g/mL范围内线性方程为△I=-55.95+46.40c(r~2=0.9985),效果令人满意。
Chemiluminescence is a light emission from chemical reactions.Chemiluminescence analysis has some advantages such as high sensitivity,wide linear range and simple instrument. It has become an attractive analytical tool in biological and chemical analysis.However,the CL analysis has also some disadvantage;the main disadvantage is very poor selectivity which limited its application widely.How to solute this problem?
One of the approaches is combining the CL analysis with high performance separation method such as the high performance liquid cheromatograpy or capillary elecrophorecence.The another approach is combining with specific molecular recognation such as enzyme reaction including pure enzyme,plant and animal tissue or cell,antibody,antigen or receptor,nucleic acid,aptamer,DNA or RNA and molecular imprinting polymer.
As a powerful modern separation technique,High Performance Liquid Chromatography (HPLC) has been widely used for the analysis of many analytes in diverse fields.Detectors are one of the most important components of HPLC system since they produce a wealth of information about the separated components which can be stored in computers and manipulated as desired to assist solute identification.In recent years,chemiluminescence(CL) as a detection technique of HPLC is very attractive due to higher sensitivity,wider linear dynamic ranges and simpler instrumentation.The advance of CL detection has greatly catalyzed the growth and popularity of HPLC-CL application,and made trace analysis possible owing to its capability of measuring pictogram or femtogram quantities of compounds in the column eluate.The investigations and applications of HPLC-CL technology are currently also an important subject, and a hot point in analytical science.The combination of HPLC separation,which is versatile and robust,and CL-based reactions,which are extremely sensitive,is promising for numerous applications in recent years.
However,the number of the practical CL methods so far reported are not so many owing to some limitation as follows:in HPLC-CL methods,the reagent such as oxidizing reagent is delivered for the post-column CL reaction using additional pump.Thus,the dilution of the analytes by mixing with reagent sometimes results in the lower sensitivity.So far the CL reagents used in HPLC are still limited,the complicated chemistry involved makes application of these reagents in HPLC even more difficult.Although many types of reactors(interfaces) have been developed;however,most of them are still in the optimization phase and mainly suited to the fast kinetic reaction.In addition,analysis of real samples in HPLC-CL is unsatisfactory probably due to matrix interference.
To solve these problems,we designed a simple reactor so extraordinary that it can obtain the most luminescent intensity as soon as the CL reaction was carried out.Moreover,there wasn't any dead volume and dilution effect.The new assemble technique based on HPLC coupled with CL detection has been successfully applied in determination of some medicinements or neurotransmitters.The effects of several parameters on the HPLC resolution and CL emission were studied systematically.Several novel methods based on HPLC with chemiluminescence detectetor have been developed for the determination of in pharmaceutical and biological samples.Coupled with microdialysis,one of the HPLC-CL systems has been applied to study the pharmacokinetics of some drugs for in-vivo,on-line and real time determination.
Microdialysis sampling has become a powerful technique for studying biochemical events in the extraceilular fluid of actually any tissue,organ or biological fluid in recent years.It is a standard technique in the neurosciences and has been extended to use in many other fields including pharmacokinetic,bioprocess monitoring etc.Microdialysis is a dynamic sampling method based on analyte diffusion across a semipermeable membrane driven by a concentration gradient.The advantage of using microdialysis sampling is that relatively low numbers of experimental animals can be used and the physiological and anatomical features of their tissue remain intact during sampling with the microdialysis probe.In addition, microdialysis sampling coupled with appropriate analytical chemical technology can be applied to continuously monitor chemical changes within the ECF with respect to time at one implantation site.Microdialysis has also the advantage that the technique is easy to automate and can be on-line coupled with many analytical techniques.On-line HPLC with microdialysis perfusion provides simplified sample preparation and automated analyses.
In this research work,we have developed a new HPLC-analysis-CL method and successfully applied it to monitor levodopa in rabbit blood in vivo and on-line.
This dissertation consists of four chapters.Chapters 1 is a review and Chapters 2 to 4 are research reports including 8 research works.
In Chapter 1,the development and tendency of the HPLC with CL detection are reviewed. It covers the principles of the HPLC with CL detector,the design of CL detectors,CL detection systems(including luminol,peroxyoxalates,Ru(bipy) 3~(2+),KMnO_4),the applications of analytical methods for many kinds of inorganic,organic and biologic samples,and the trends of HPLC-CL in environmental,life science,pharmacy and clinical medical science.
The research works includes:
(1) High Performance Liquid Chromatography-Chemiluminescence Detection for the in vivo on-line determination and study of the pharmacokinetics of Levodopa in blood with microdialysis sampling
A simple,reliable and reproducible method for in vivo on-line separation and determination of ievodopa based on high performance liquid chromatography with chemiluminescence detection and microdialysis is described.The perfusate is perfused at a flow rate of 5μL/min. The concentration of levodopa in the dialysate is determined on line with a chemiluminescence system.The dialysate sample volume is about 20μL.The system is linearly related to the concentration of levodopa in the range 1×10~(-8)-1×10~(-6)g/mL(r~2 =0.9995) with a detection l imit(3σ) of 3×10~(-9) g/mL and the sample throughput of 12h~(-1),RSD is 2.8%(n=11).The method has been successfully applied to study the pharmacokinetics of levodopa in vivo,and the C_(max),AUC_(0-t) and T_(max) value of the pharmacokinetics parameter are 16.60ng/mL,20.92ng/mL,90min respectively.
(2) Simultaneous determination of Epinephrine,Noradrenaline and Dopamine in human serum samples by high performance liquid chromatography with chemiluminescence detection
A simple,rapid and accurate high performance liquid chromatographic(HPLC) technique coupled with chemiluminescence(CL) detection was developed for the simultaneous determination of epinephrine(E),noradrenaline(NA) and dopamine(DA).It was based on the analyte enhancement effect on the CL reaction between luminol and potassium ferricyanide.The effects of various parameters,such as potassium ferricyanide concentration,luminol concentration,pH value and component of the mobile phase on chromatographic behaviors of the analytes(E,NA and DA) were investigated.The separation was carried out on C_(18) column using the mobile phase of 0.01 mol/L potassium hydrogen phthalate solution and methanol(92:8,ν/ν).Under the optimum conditions,E,NA and DA showed good linear relationships in the range of 1×10~(-8)-5×10~(-6),5.0×10~(-9)-1.0×10~(-6) and 5.0×10~(-9)-1.0×10~(-6)g/mL respectively.The detection limits for E,NA and DA were 4.0×10~(-9),1.0×10~(-9) and 8.0×10~(-10)g/mL.The proposed method has been applied successfully to the analysis of E,NA and DA in human serum samples.
(3) Determination of Inosine in human serum using high-performance liquid chromatography with chemiluminescence detection
Based on the sensitizing effect of formaldehyde on the chemiluminescence(CL) reaction of Inosine with acidic potassium permanganate and the combination technique of high-performance liquid chromatography(HPLC),a sensitive,selective and simple post-column CL detection method for determining Inosine is described.The optimal conditions for the CL detection and HPLC separation were carried out.The linear range is 0.4-12μg mL~(-1) for Inosine.The detection limit of is 0.1μg mL~(-1) and the relative standard deviation with a concentration of 0.15×10~(-6) g/mL was 2.9%respectively(n=9).The method has been satisfactorily applied to the determination of lnosine in pharmaceutical preparations and human serum samples
(4) High Performance Liquid Chromatography-Chemiluminescence Detection for Vitamin B6 in human serum
This paper described a sensitive,selective and simple post-column CL detection method for determining VB_6.It was based on the sensitizing effect of formaldehyde on the chemiluminescence(CL) reaction of VB_6 with acidic potassium permanganate and the combination technique of high-performance liquid chromatography(HPLC).The optimal conditions for the CL detection and HPLC separation were carried out.The linear range is 0.3-10μg mL~(-1) for VB6,the detection limit of is 0.1μgmL~(-1) and the relative standard deviation with a concentrati on of 1.0×10~(-6) g/mL was 3.7%for VB_6(n=7).The method has been satisfactorily applied to the determination of VB_6 in pharmaceutical preparations and human serum samples
(5) Determination of Promethazine Hydrochioride in human urine using high-performance liquid chromatography with chemiluminescence detection
A sensitive,selective and simple post-column CL detection method for determining Promethazine Hydrochloride is described based on the sensitizing effect of formaldehyde on the chemiluminescence(CL) reaction of Promethazine Hydrochloride with acidic potassium permanganate and the combination technique of high-performance liquid chromatography (HPLC),The optimal conditions for the CL detection and HPLC separation were carried out.The linear range is 1--100μg mL~(-1) for Promethazine Hydrochloride,the detection limit of is 0.3μgmL~(-1) and the relative standard deviation with a concentration of 1.0×10~(-6) g/mL was 2.7% for Promethazine Hydrochloride(n=11).The method has been satisfactorily applied to the determination ofPromethazine Hydroehloride in human urine samples
(6) Chemiluminescent detection of fruoside in serum and urine samples after HPLC separation
A novel method was developed for the determination of fruoside by high-performance liquid chromatography(HPLC) coupled with chemiluminescence(CL) detection.The separation was carried out with an isocratic elution using the mobile phase of 50:49:1(ν/ν/ν) water-methanol -phosphate buffer(containing 7.0×10~(-4)M Potassium dihydrogen phosphate,pH 3.0) at a flow rate of 1.1 mL/min.The CL intensity was linear within the range of 1～50×10~(-7)g/mL to the fruoside's concentration,and the detection limits at a signal-to-noise of 3 was 3.0×10~(-8)g/mL.The method was successfully applied to the determination of fruoside in serum and urine samples.The possible mechanism of the CL reaction was also discussed briefly.
(7)Development of a HPLC-chemiluminescence assay for diethylstilbestrol(DES) in tablets and serum samples
A new,highly sensitive chemiluminescence method for measurement of diethylstilbestrol (DES) in various substances such as human serum and tablets has been developed.The method is based on reverse-phase high performance liquid chromatographic separation and subsequent tris(2,2'-bipyridine)ruthenium(Ⅱ)-Ce(Ⅳ) chemiluminescence detection.It was confirmed that DES show strong chemiluminescence upon mixing with tris(2,2′-bipyridine) ruthenium(Ⅱ)-Ce(Ⅳ). A calibration graph,based on a standard DES solution,was linear over the range 8×10~(-8)～1×10~(-5)g/mL and the detection limit was 3.0×10~(-8)g/mL(signal-to-noise ratio=3).This highly sensitive and selective determination method can be applied to selected samples without purification or pre-concentration procedures.The proposed method is easier,more sensitive,and time-saving.
(8)Analysis of phentolamine by HPLC with Ru(bipy)_3Cl_2-Ce(Ⅳ) chemiluminescence detection
A simple,selective and sensitive method for the determination of phentolamine has been developed using high-performance liquid chromatography with chemiluminescence detection. The phentolamine were separated on a C_(18) reversed-phase column with an isocratic elution using the mobile phase of 50:49:1(ν/ν/ν) water-methanol-phosphate buffer(containing 7.0×10~(-4)M Potassium dihydrophosphate,pH 3.0) at a flow rate of 0.8mL/min.The eluate was mixed with tris(2,2′-bipyridyl)ruthenium(Ⅱ)-Ce(Ⅳ),and the generated chemiluminescence was detected. Calibration graphs,based on standard solutions,were linear over the range 1～20×10~(-7)g/mL.The detection limits at a signal-to-noise ratio of 3 ranged 3.0×10~(-8)g/mL.The relative standard deviations was 3.1%.This HPLC system was successfully applied to the determination of phentolamine in serum and urine samples.
引文
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