2-(2-羟基-3-甲氧基苯基)-5-(1-羟甲基)C_(60)吡咯烷衍生物的合成及其在DNA电化学传感器中的应用  

Synthesis of 2-( 2-Hydroxy-3-methoxyl-phenyl)-5-( 1-hydroxymethyl) C_(60) Pyrrolidine Derivative and Its Application in Electrochemical DNA Sensors

作　　者：苑小宁[1] 邱玮玮[1] 李拂晓[1] 谢丽清[1] 徐飘扬[1] 高凤[1] 汪庆祥[1] 高飞[1] 

机构地区：[1]闽南师范大学化学与环境学院福建省现代分离分析科学与技术重点实验室,福建漳州363000

出　　处：《分析测试学报》2015年第5期512-518,共7页Journal of Instrumental Analysis

基　　金：国家自然科学基金项目(21275127;21301143);福建省教育厅重点项目(JA11166);福建省高等学校新世纪优秀人才支持计划(JA12204);福建省教育厅项目(JA14195)

摘　　要：以L-丝氨酸、邻香兰素及C60为原料通过1,3-偶极环加成反应,合成并分离纯化得到一种新型的2-（2-羟基-3-甲氧基苯基）-5-（1-羟甲基）C60吡咯烷衍生物（FPD）。通过质谱、红外光谱、紫外-可见光谱、氢核磁和元素分析等检测手段对其结构进行表征。采用滴涂法将FPD修饰在玻碳电极表面,然后在其表面组装Al3＋,并进一步利用Al3＋与磷酸骨架的静电相互作用,将探针DNA固定到修饰电极表面,组建了一种新型DNA电化学生物传感器。以亚甲基蓝（MB）为杂交指示剂,考察了该DNA传感器的分析性能。实验结果表明,在1.0×10-15~1.0×10-9mol/L浓度范围内,互补序列DNA的浓度对数值（lgcS2）与该传感器上的峰电流值（Ip）具有良好的线性关系,其线性方程为Ip（10-6A）=0.106 lg（cS2,mol/L）＋0.735,检出限（S/N=3）为5.4×10-16mol/L。选择性实验表明该传感器能有效识别互补序列和碱基错配序列DNA片段。A new compound 2-（ 2-hydroxy-3-methoxyl-phenyl）-5-（ 1-hydroxymethyl） C60 pyrrolidine derivative（ FPD） was successfully synthesized with 1,3-dipolar cycloaddition reaction of C60 with ovanillin and L-serine. Its structure was characterized by MS,FT-IR,UV-Vis,1H NMR and elemental analysis. FPD was immobilized on the surface of glassy carbon electrode（ GCE） by drop coating method,and then Al3 ＋was assembled on its surface. The probe DNA was fixed on the electrode surface by the electrostatic interaction between the negatively charged phosphate group of DNA and Al3 ＋,and a new electrochemical DNA sensor was constructed successfully. The analytical performance of the biosensor was evaluated using methylene blue as the hybridization indicator. The results showed that a good linear relationship between peak currents signals of MB and logarithm value of the target compound concentrations（ lgcS2） in the range of 1. 0 × 10-15-1. 0 × 10-9mol / L was obtained,with a linear regression equation of Ip（ 10-6A） = 0. 106 lg（ cS2,mol/L） ＋ 0. 735 and a limit of detection（ S / N = 3） of 5. 4 × 10-16 mol / L. The selectivity experiments further showed that the complementary sequences and the base mismatch sequences could be well distinguished with this biosensor.

关 键 词：C60吡咯烷衍生物 DNA传感器 铝离子 亚甲基蓝 

分 类 号：O657.1[理学—分析化学] O629.74[理学—化学]