BODIPY-肼新荧光标记试剂及其测定羰基化合物分析方法研究
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摘要
随着生命科学、环境科学、材料科学的发展,对分析方法的灵敏度和选择性提出了新的要求。高效液相色谱(HPLC)是到目前为止人类掌握的对复杂混合物分离能力最强、分析范围最广的工具之一。然而,由于一些样品中被测组分含量极低或其本身某些物理、化学性质的限制,导致很多化合物不能被灵敏检出或不能直接用于液相色谱分析,因而限制了HPLC的适用范围。化学衍生法是借助化学反应将待测组份接上某种特定基团,从而改善检测方法的灵敏度和选择性以及改善分离效果的方法。由于荧光检测的灵敏度比紫外检测一般要高1-3个数量级,现已成为色谱分离中最常用的超灵敏检测方法之一；因此将荧光试剂的化学衍生法与高效液相色谱-荧光检测(HPLC-FD)相结合实现对被测组分的高效分离与灵敏检测,是提高分析方法的灵敏度和改善分析方法的选择性的重要手段。因而开发性能优异的荧光衍生试剂在色谱分析中具有重要地位。
羰基化合物在环境、生物体中广泛存在。环境中的某些挥发性醛酮化合物威胁到人类的健康；生物体的某些羰基化合物含量虽少,但却对生命活动有重要影响。因而开展环境、生物体系中的羰基化合物分析具有重要意义。二氟化硼-二吡咯甲烷(BODIPY)是一类具有较高的荧光量子产率(典型0.6-1.0)和摩尔吸光系数(一般60000-80000 M-1cm-1)的荧光团,其荧光强度对PH以及溶剂不敏感,窄的吸收、发射带宽等综合荧光性能已优于荧光素、四甲基罗丹明、得克萨斯红等染料。并且通过结构设计可以调节该染料的荧光量子产率和发射波长。1,3,5,7-四甲基取代的BODIPY,其荧光激发波长在490nm左右,与商业化的氩离子激光器波长(488 nm)相匹配。基于上述思想,本论文设计在1,3,5,7-四甲基取代的BODIPY母核上引入肼功能团,开发用于测定羰基化合物的荧光衍生试剂和建立新的HPLC-FD测定羰基化合物的分析方法。本论文的主要研究内容如下：
(1)设计、合成了以丙酰肼和丁酰肼为反应基团,以1,3,5,7-四甲基取代的BODIPY为荧光团的两种新型标记羰基的荧光试剂：1,3,5,7-四甲基-8-丙酰肼-二氟化硼-二毗咯甲烷(BODIPY-丙酰肼)和1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷(BODIPY-丁酰肼)。并对它们的结构进行了表征并对合成方法进行了探讨。
(2)对所合成的两种BODIPY-肼试剂(1,3,5,7-四甲基-8-丙酰肼-二氟化硼-二吡咯甲烷和1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷)及其与模型醛的衍生产物的荧光性质进行了较系统研究,讨论了各种因素对试剂及其衍生产物荧光性质的影响。实验发现,开发出来的两种BODIPY肼试剂及其与醛(酮)的衍生产物具有相同的荧光激发光谱和荧光发射光谱(λex/λem=495nm/505nm),而且与羰基化合物的衍生产物荧光量子产率高(>0.90),光稳定性好、荧光强度受pH值影响小。这些荧光性质表明开发出来的两种BODIPY肼试剂是一类优秀的羰基化合物衍生试剂,可以进一步用于HPLC-FD。
(3)分别以1,3,5,7-四甲基-8-丙酰肼-二氟化硼-二吡咯甲烷(BODIPY-丙酰肼)和1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷(BODIPY-丁酰肼)为柱前荧光衍生试剂用于高效液相色谱分离荧光检测甲醛、乙醛、丙醛、丁醛、戊醛、已醛、庚醛、辛醛、壬醛、癸醛、十一醛、十二醛等十二种脂肪醛。通过对衍生条件和分离条件进行优化,建立了测定脂肪醛的HPLC-FD的新方法。衍生反应以H3PO4作催化剂,在60℃时试剂与脂肪醛30min内反应完全,生成稳定的衍生产物。采用C18柱分离衍生产物,以含20%THF乙腈和pH6.5的HCOOH-NH3的缓冲溶液为流动相作梯度洗脱,在λex/λem=490nm/510nm下荧光检测,衍生物在17分钟内得到较好的分离。试剂BODIPY-丙酰肼测定脂肪醛的线性范围为0.01-2.00μmolL-1,检测限为0.23-0.78nmol L-1。相对标准偏差值(R.S.D),日内检测为1.2-2.9%,日间检测为1.4-3.1%(平行测定6次,n=6)。该试剂用于白酒中脂肪醛含量测定,加标回收率在95%-105%。试剂BODIPY-丁酰肼测定脂肪醛的线性范围为0.01-1μmol L-1,检测限为0.43-0.69nmol L-1,该试剂用于人血清中脂肪醛含量测定,回收率在96%-105%之间。
(4)以1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷荧光衍生试剂作为柱前衍生试剂,以茉莉酸为检测对象,对衍生条件和分离条件进行了优化,建立了高效液相色谱分离荧光检测植物组织中茉莉酸含量的新方法。试剂与茉莉酸在H3P04催化下60℃反应30min生成稳定衍生产物。采用C18柱分离衍生产物,λex/λem=490/510nm下荧光检测,以含30mmol L-1 pH6.5HCOOH-NH3缓冲溶液的甲醇-水-THF(67：30：3,v/v/v)为流动相作等度洗脱,流速为1ml/min,在11min内能够较好的分离衍生产物,检出限为5.7×10-11mol L-1。该方法简单,重现性好,并将该方法用于植物样品中茉莉酸含量的测定,回收率在97.2-103.6%。
(5)以1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷荧光衍生试剂作为柱前衍生试剂,以茉莉酸甲酯和茉莉酸二氢甲酯为检测对象,对衍生条件和分离条件进行了优化,建立了高效液相色谱分离荧光检测植物组织中两种茉莉酸甲酯含量的新方法。试剂与两种茉莉酸甲酯在H3P04催化下80℃反应2.5h生成稳定衍生产物。采用C18柱分离衍生产物,λex/λem=490/510nm下荧光检测,以含50mmolL-1 pH6.0乙酸-三乙胺缓冲液的甲醇-水(90:10,v/v)为流动相作等度洗脱,流速为0.8ml/min,两种衍生产物在15min内能够较好的分离,线性范围为0.001-0.1μmol L-1,对茉莉酸甲酯和茉莉酸二氢甲酯的检测限分别为0.2nmol L-1和0.3nmol L-1。该方法灵敏度高,重现性好,并将该方法用于植物组织萃取液样品中茉莉酸甲酯和茉莉酸二氢甲酯含量的测定,回收率在92.4-104.4%。
(6)以BODIPY-丁酰肼为柱前衍生试剂,以9种还原糖(D-葡萄糖、L-鼠李糖、D-甘露糖、D-乳糖、D-果糖、D-核糖、麦芽糖、D-木糖、D-半乳糖)为研究对象,通过对衍生条件和分离条件的优化,建立HPLC-FD测定还原糖的方法。试剂与9种还原糖在H3P04催化下80℃反应2.5h生成稳定衍生产物。采用C18柱分离衍生产物,λex/λem=490/510nm下荧光检测,以含100mmol L-1 pH6.0乙酸-三乙胺缓冲液的乙腈-水(30:10,v/v)为流动相作等度洗脱,流速为0.8ml/min,9种糖衍生产物在30min内能得到较好的分离,线性范围为0.005-0.1μmol L-1,对糖的检测限在为0.2-1.Onmol L-1之间。该方法灵敏度高,重现性好,并将该方法用于人唾液样品中还原糖的测定。
The development of life science, environmental science and materials science put forward new demands on the sensitivity and selectivity of analytical methods in analytical chemistry. High performance liquid chromatography (HPLC) has been enthusiastically and widely used in many fields of industry and scientific research for its powerful separation and analysis capacities. However, there are many compounds which are not suitable to be directly analyzed by HPLC or cannot be sensitively detected by HPLC because of the properties of the corresponding compounds or lacking of strong chromophore. This limits the analytical scope of HPLC and its farther application. Chemical derivatization was adopted to solve the above problems by attaching strong chromophore to the analytes. As fluorescence detection is one of the most sensitive detection technologies in HPLC, derivatization of analytes with fluorescence labeling reagents coupled with HPLC-fluorescence detection (FD) or laser-induced fluorescence detection (LIFD) has been widely adopted. So developing new flurescent derivatization reagents and exploit their application in HPLC is one of the active research areas for HPLC.
Carbonyl compounds are the ones of most important compounds in nature which exists extensively. They are present in a number of low molecular weight molecules such as drugs, steroid hormones, reducing sugars and some metabolic intermediates such as pyruvate and a-ketoglutarate. Some of carbonyl compounds, such as formaldehyde, acetaldehyde, hexanal, heptanal are harmful to human body, the concentration of them often be the markers of some diseases. Some of carbonyl compounds, such as carbohydrate, progesterone play significant roles in living activities. Therefore, development of fluorescent derivatization reagents for carbonyl compounds in environmental analysis and bioanalysis has important significance.
Boradiazaindacenes (BODIPY or boradipyrrin dyes) are interesting fluorophores with many applications in fields as diverse as fluorescent labels, chemosensors, light harvesting systems, and photodynamic therapy. Their high quantum yields (typically 0.6-1.0) and large extinction coefficients (60 000-80 000 M-1cm-1) are the two main reasons for their widespread utilization. The typical peak excitation wavelength of an 1,3,5,7-tetramethyl-substituted boradiazaindacene is around 490 nm, which exactly matches the 488 nm argon-ion laser. BODIPY-based hydrazine reagents for labeling carbonyl compounds are developed for this purpose. The major contents in this dissertation are described as follows:
(1) Two new hydrazine reagents using BODIPY as a fluorophore were designed and synthesized. They were 1,3,5,7-tetramethyl-8-propionohydrazide-difluoroboradiaza-s-indacene (BODIPY-propionohydrazide) and 1,3,5,7-tetramethyl-8-aminozide- difluoroboradiaza-s-indacene (BODIPY-aminozide). The conditions of synthesis have been investigated and the structures of all new compounds are identified with MS and 1H NMR.
(2) The effect of different environments on the fluorescent properties of new reagents and their derivatives were studied and discussed; the relation between molecule structure and fluorescent properties was discussed; and the feasibility of the application on the HPLC was discussed. The result shows the derivatives of the reagents with carbonyl compounds have good photostability, high extinction coefficient (8.40×104 M-1cm-1) and high fluorescence quantum yields (0.94 in acetonitrile). The spectra of derivatives of carbonyl compounds are also relatively insensitive to solvent polarity and pH because of lack of ionic charge. All of the derivatives have good fluorescent properties and are suited for fluorescent detection in HPLC.
(3) The newly synthesized BODIPY-based fluorescent derivatization reagents, 1,3,5,7-tetramethyl-8-propionohydrazide-difluoroboradiaza-s-indacene (BODIPY-propionohydrazide) and 1,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide), have been used as a pre-column derivatization reagent for the determination of twelve aliphatic aldehydes (C1-C12) with high performance liquid chromatography (HPLC) for the first time. The derivatization reaction of BODIPY-hydrazide reagent with aliphatic aldehydes was completed at 60℃for 0.5 h using phosphorous acid as a catalyst. On a C18 column, the derivatives of twelve aliphatic aldehydes could be seperated in 17 min using a mobile phase of acetonitrile-tetrahydrofuran (THF)-water as mobile phase containing 30 mol L-1 formic acid/ammonia buffer (pH 6.50) with fluorescence detection atλex/λem= 490/510 nm. The detection limits for aliphatic aldehydes could reach 0.23-0.78 nmol L-1 (signal-to-noise=3) with BODIPY-propionohydrazide and 0.43-0.68 nmol L-1 (signal-to-noise=3) with BODIPY-aminozide. The proposed motheds were applied for the determination of the aliphatic aldehydes in wines and human serum samples with good recovery, respectly.
(4) A highly sensitive and selective high performance liquid chromatographic method for one of signaling phytohormones, jasmonic acid (JA), has been developed based on pre-column derivatization with 1,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide). The derivatization reaction was carried out at 60℃for 30 min in the presence of phosphoric acid. The formed JA derivative was eluted using a mobile phase of methanol/ammonium formate buffer (pH 6.50)/tetrahydrofuran (THF) (67:30:3, v/v/v) in 10 min on a C18 column and detected with fluorescence detection at excitation and emission wavelengths of 495 and 505 nm, respectively. The detection limit (signal-to-noise ratio=3) reached 5.7×i0-11mol L-1 or 1.14 fmol per injection (20μL), which is the lowest in the existing methods. Moreover, jasmonic acid in samples could be quantified at an original concentration as low as 5.0×10-10 mol L-1. The proposed method has been successfully applied to the direct determination of trace jasmonic acid in the crude extracts of soybean leaves with recoveries of 95-104%.
(5) A new method is described for the determination of endogenous methyl Jasmonate (Me-JA) and methyl dihydro-jasmonate (Me-DHJA) in Jasmine extracts using liquid chromatography (LC) with fluorescence detection. Plant tissues were extracted and derivatized using l,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide). The derivatization reaction was completed at 80℃for 2.5h in the presence of phosphorous acid catalyst without further transfer steps. Derivatives of Me-JA and Me-DHJA were separated with isocratic elution on a C18 reversed-phase column using methanol-water=90:10 (v/v) containing 50mM acetic acid/triethylamine buffer solution (pH 6.00) as a mobile phase and detected by a fluorescence detector at excitation and emission wavelengths of 490 and 510 nm, respectively. The detection limits of Me-JA and Me-DHJA were 0.2nmol L-1 and 0.3 nmol L-1 (signal-to-noise ratio=3).
(6) A novel labeling reagent 1,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide) coupled with high performance liquid chromatography (HPLC) with fluorescence detection (FD) for the determination of carbohydrates has been developed. The method for the derivatization of carbohydrates with BODIPY-aminozide is simplified. The derivatization reaction was completed at 80℃for 2.5h in the presence of phosphorous acid catalyst without further transfer steps. Nine monosaccharide derivatives such as lactose, maltose, galactose, mannose, glucose, fructose, ribose, xylose and rhamnose can successfully separated using a mobile phase of 25% v/v acetonitrile in 100 mmol L-1 acetic acid/ triethylamine buffer solution (pH 6.00) in 30 min on a C18 column with fluorescence detection (λex/λem=490/510 nm). Good linearity was obtained with a correlation coefficient in the range of 0.9983-0.9999, the limits of detection and quantitation being 0.2-1 nmol L"1 and 4-20 fmol, respectively. Furthermore, the developed method has been successfully applied to the analysis of carbohydrates in human saliva samples.
羰基化合物在环境、生物体中广泛存在。环境中的某些挥发性醛酮化合物威胁到人类的健康；生物体的某些羰基化合物含量虽少,但却对生命活动有重要影响。因而开展环境、生物体系中的羰基化合物分析具有重要意义。二氟化硼-二吡咯甲烷(BODIPY)是一类具有较高的荧光量子产率(典型0.6-1.0)和摩尔吸光系数(一般60000-80000 M-1cm-1)的荧光团,其荧光强度对PH以及溶剂不敏感,窄的吸收、发射带宽等综合荧光性能已优于荧光素、四甲基罗丹明、得克萨斯红等染料。并且通过结构设计可以调节该染料的荧光量子产率和发射波长。1,3,5,7-四甲基取代的BODIPY,其荧光激发波长在490nm左右,与商业化的氩离子激光器波长(488 nm)相匹配。基于上述思想,本论文设计在1,3,5,7-四甲基取代的BODIPY母核上引入肼功能团,开发用于测定羰基化合物的荧光衍生试剂和建立新的HPLC-FD测定羰基化合物的分析方法。本论文的主要研究内容如下：
(1)设计、合成了以丙酰肼和丁酰肼为反应基团,以1,3,5,7-四甲基取代的BODIPY为荧光团的两种新型标记羰基的荧光试剂：1,3,5,7-四甲基-8-丙酰肼-二氟化硼-二毗咯甲烷(BODIPY-丙酰肼)和1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷(BODIPY-丁酰肼)。并对它们的结构进行了表征并对合成方法进行了探讨。
(2)对所合成的两种BODIPY-肼试剂(1,3,5,7-四甲基-8-丙酰肼-二氟化硼-二吡咯甲烷和1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷)及其与模型醛的衍生产物的荧光性质进行了较系统研究,讨论了各种因素对试剂及其衍生产物荧光性质的影响。实验发现,开发出来的两种BODIPY肼试剂及其与醛(酮)的衍生产物具有相同的荧光激发光谱和荧光发射光谱(λex/λem=495nm/505nm),而且与羰基化合物的衍生产物荧光量子产率高(>0.90),光稳定性好、荧光强度受pH值影响小。这些荧光性质表明开发出来的两种BODIPY肼试剂是一类优秀的羰基化合物衍生试剂,可以进一步用于HPLC-FD。
(3)分别以1,3,5,7-四甲基-8-丙酰肼-二氟化硼-二吡咯甲烷(BODIPY-丙酰肼)和1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷(BODIPY-丁酰肼)为柱前荧光衍生试剂用于高效液相色谱分离荧光检测甲醛、乙醛、丙醛、丁醛、戊醛、已醛、庚醛、辛醛、壬醛、癸醛、十一醛、十二醛等十二种脂肪醛。通过对衍生条件和分离条件进行优化,建立了测定脂肪醛的HPLC-FD的新方法。衍生反应以H3PO4作催化剂,在60℃时试剂与脂肪醛30min内反应完全,生成稳定的衍生产物。采用C18柱分离衍生产物,以含20%THF乙腈和pH6.5的HCOOH-NH3的缓冲溶液为流动相作梯度洗脱,在λex/λem=490nm/510nm下荧光检测,衍生物在17分钟内得到较好的分离。试剂BODIPY-丙酰肼测定脂肪醛的线性范围为0.01-2.00μmolL-1,检测限为0.23-0.78nmol L-1。相对标准偏差值(R.S.D),日内检测为1.2-2.9%,日间检测为1.4-3.1%(平行测定6次,n=6)。该试剂用于白酒中脂肪醛含量测定,加标回收率在95%-105%。试剂BODIPY-丁酰肼测定脂肪醛的线性范围为0.01-1μmol L-1,检测限为0.43-0.69nmol L-1,该试剂用于人血清中脂肪醛含量测定,回收率在96%-105%之间。
(4)以1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷荧光衍生试剂作为柱前衍生试剂,以茉莉酸为检测对象,对衍生条件和分离条件进行了优化,建立了高效液相色谱分离荧光检测植物组织中茉莉酸含量的新方法。试剂与茉莉酸在H3P04催化下60℃反应30min生成稳定衍生产物。采用C18柱分离衍生产物,λex/λem=490/510nm下荧光检测,以含30mmol L-1 pH6.5HCOOH-NH3缓冲溶液的甲醇-水-THF(67：30：3,v/v/v)为流动相作等度洗脱,流速为1ml/min,在11min内能够较好的分离衍生产物,检出限为5.7×10-11mol L-1。该方法简单,重现性好,并将该方法用于植物样品中茉莉酸含量的测定,回收率在97.2-103.6%。
(5)以1,3,5,7-四甲基-8-丁酰肼-二氟化硼-二吡咯甲烷荧光衍生试剂作为柱前衍生试剂,以茉莉酸甲酯和茉莉酸二氢甲酯为检测对象,对衍生条件和分离条件进行了优化,建立了高效液相色谱分离荧光检测植物组织中两种茉莉酸甲酯含量的新方法。试剂与两种茉莉酸甲酯在H3P04催化下80℃反应2.5h生成稳定衍生产物。采用C18柱分离衍生产物,λex/λem=490/510nm下荧光检测,以含50mmolL-1 pH6.0乙酸-三乙胺缓冲液的甲醇-水(90:10,v/v)为流动相作等度洗脱,流速为0.8ml/min,两种衍生产物在15min内能够较好的分离,线性范围为0.001-0.1μmol L-1,对茉莉酸甲酯和茉莉酸二氢甲酯的检测限分别为0.2nmol L-1和0.3nmol L-1。该方法灵敏度高,重现性好,并将该方法用于植物组织萃取液样品中茉莉酸甲酯和茉莉酸二氢甲酯含量的测定,回收率在92.4-104.4%。
(6)以BODIPY-丁酰肼为柱前衍生试剂,以9种还原糖(D-葡萄糖、L-鼠李糖、D-甘露糖、D-乳糖、D-果糖、D-核糖、麦芽糖、D-木糖、D-半乳糖)为研究对象,通过对衍生条件和分离条件的优化,建立HPLC-FD测定还原糖的方法。试剂与9种还原糖在H3P04催化下80℃反应2.5h生成稳定衍生产物。采用C18柱分离衍生产物,λex/λem=490/510nm下荧光检测,以含100mmol L-1 pH6.0乙酸-三乙胺缓冲液的乙腈-水(30:10,v/v)为流动相作等度洗脱,流速为0.8ml/min,9种糖衍生产物在30min内能得到较好的分离,线性范围为0.005-0.1μmol L-1,对糖的检测限在为0.2-1.Onmol L-1之间。该方法灵敏度高,重现性好,并将该方法用于人唾液样品中还原糖的测定。
The development of life science, environmental science and materials science put forward new demands on the sensitivity and selectivity of analytical methods in analytical chemistry. High performance liquid chromatography (HPLC) has been enthusiastically and widely used in many fields of industry and scientific research for its powerful separation and analysis capacities. However, there are many compounds which are not suitable to be directly analyzed by HPLC or cannot be sensitively detected by HPLC because of the properties of the corresponding compounds or lacking of strong chromophore. This limits the analytical scope of HPLC and its farther application. Chemical derivatization was adopted to solve the above problems by attaching strong chromophore to the analytes. As fluorescence detection is one of the most sensitive detection technologies in HPLC, derivatization of analytes with fluorescence labeling reagents coupled with HPLC-fluorescence detection (FD) or laser-induced fluorescence detection (LIFD) has been widely adopted. So developing new flurescent derivatization reagents and exploit their application in HPLC is one of the active research areas for HPLC.
Carbonyl compounds are the ones of most important compounds in nature which exists extensively. They are present in a number of low molecular weight molecules such as drugs, steroid hormones, reducing sugars and some metabolic intermediates such as pyruvate and a-ketoglutarate. Some of carbonyl compounds, such as formaldehyde, acetaldehyde, hexanal, heptanal are harmful to human body, the concentration of them often be the markers of some diseases. Some of carbonyl compounds, such as carbohydrate, progesterone play significant roles in living activities. Therefore, development of fluorescent derivatization reagents for carbonyl compounds in environmental analysis and bioanalysis has important significance.
Boradiazaindacenes (BODIPY or boradipyrrin dyes) are interesting fluorophores with many applications in fields as diverse as fluorescent labels, chemosensors, light harvesting systems, and photodynamic therapy. Their high quantum yields (typically 0.6-1.0) and large extinction coefficients (60 000-80 000 M-1cm-1) are the two main reasons for their widespread utilization. The typical peak excitation wavelength of an 1,3,5,7-tetramethyl-substituted boradiazaindacene is around 490 nm, which exactly matches the 488 nm argon-ion laser. BODIPY-based hydrazine reagents for labeling carbonyl compounds are developed for this purpose. The major contents in this dissertation are described as follows:
(1) Two new hydrazine reagents using BODIPY as a fluorophore were designed and synthesized. They were 1,3,5,7-tetramethyl-8-propionohydrazide-difluoroboradiaza-s-indacene (BODIPY-propionohydrazide) and 1,3,5,7-tetramethyl-8-aminozide- difluoroboradiaza-s-indacene (BODIPY-aminozide). The conditions of synthesis have been investigated and the structures of all new compounds are identified with MS and 1H NMR.
(2) The effect of different environments on the fluorescent properties of new reagents and their derivatives were studied and discussed; the relation between molecule structure and fluorescent properties was discussed; and the feasibility of the application on the HPLC was discussed. The result shows the derivatives of the reagents with carbonyl compounds have good photostability, high extinction coefficient (8.40×104 M-1cm-1) and high fluorescence quantum yields (0.94 in acetonitrile). The spectra of derivatives of carbonyl compounds are also relatively insensitive to solvent polarity and pH because of lack of ionic charge. All of the derivatives have good fluorescent properties and are suited for fluorescent detection in HPLC.
(3) The newly synthesized BODIPY-based fluorescent derivatization reagents, 1,3,5,7-tetramethyl-8-propionohydrazide-difluoroboradiaza-s-indacene (BODIPY-propionohydrazide) and 1,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide), have been used as a pre-column derivatization reagent for the determination of twelve aliphatic aldehydes (C1-C12) with high performance liquid chromatography (HPLC) for the first time. The derivatization reaction of BODIPY-hydrazide reagent with aliphatic aldehydes was completed at 60℃for 0.5 h using phosphorous acid as a catalyst. On a C18 column, the derivatives of twelve aliphatic aldehydes could be seperated in 17 min using a mobile phase of acetonitrile-tetrahydrofuran (THF)-water as mobile phase containing 30 mol L-1 formic acid/ammonia buffer (pH 6.50) with fluorescence detection atλex/λem= 490/510 nm. The detection limits for aliphatic aldehydes could reach 0.23-0.78 nmol L-1 (signal-to-noise=3) with BODIPY-propionohydrazide and 0.43-0.68 nmol L-1 (signal-to-noise=3) with BODIPY-aminozide. The proposed motheds were applied for the determination of the aliphatic aldehydes in wines and human serum samples with good recovery, respectly.
(4) A highly sensitive and selective high performance liquid chromatographic method for one of signaling phytohormones, jasmonic acid (JA), has been developed based on pre-column derivatization with 1,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide). The derivatization reaction was carried out at 60℃for 30 min in the presence of phosphoric acid. The formed JA derivative was eluted using a mobile phase of methanol/ammonium formate buffer (pH 6.50)/tetrahydrofuran (THF) (67:30:3, v/v/v) in 10 min on a C18 column and detected with fluorescence detection at excitation and emission wavelengths of 495 and 505 nm, respectively. The detection limit (signal-to-noise ratio=3) reached 5.7×i0-11mol L-1 or 1.14 fmol per injection (20μL), which is the lowest in the existing methods. Moreover, jasmonic acid in samples could be quantified at an original concentration as low as 5.0×10-10 mol L-1. The proposed method has been successfully applied to the direct determination of trace jasmonic acid in the crude extracts of soybean leaves with recoveries of 95-104%.
(5) A new method is described for the determination of endogenous methyl Jasmonate (Me-JA) and methyl dihydro-jasmonate (Me-DHJA) in Jasmine extracts using liquid chromatography (LC) with fluorescence detection. Plant tissues were extracted and derivatized using l,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide). The derivatization reaction was completed at 80℃for 2.5h in the presence of phosphorous acid catalyst without further transfer steps. Derivatives of Me-JA and Me-DHJA were separated with isocratic elution on a C18 reversed-phase column using methanol-water=90:10 (v/v) containing 50mM acetic acid/triethylamine buffer solution (pH 6.00) as a mobile phase and detected by a fluorescence detector at excitation and emission wavelengths of 490 and 510 nm, respectively. The detection limits of Me-JA and Me-DHJA were 0.2nmol L-1 and 0.3 nmol L-1 (signal-to-noise ratio=3).
(6) A novel labeling reagent 1,3,5,7-tetramethyl-8-aminozide-difluoroboradiaza-s-indacene (BODIPY-aminozide) coupled with high performance liquid chromatography (HPLC) with fluorescence detection (FD) for the determination of carbohydrates has been developed. The method for the derivatization of carbohydrates with BODIPY-aminozide is simplified. The derivatization reaction was completed at 80℃for 2.5h in the presence of phosphorous acid catalyst without further transfer steps. Nine monosaccharide derivatives such as lactose, maltose, galactose, mannose, glucose, fructose, ribose, xylose and rhamnose can successfully separated using a mobile phase of 25% v/v acetonitrile in 100 mmol L-1 acetic acid/ triethylamine buffer solution (pH 6.00) in 30 min on a C18 column with fluorescence detection (λex/λem=490/510 nm). Good linearity was obtained with a correlation coefficient in the range of 0.9983-0.9999, the limits of detection and quantitation being 0.2-1 nmol L"1 and 4-20 fmol, respectively. Furthermore, the developed method has been successfully applied to the analysis of carbohydrates in human saliva samples.
引文
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