十元瓜环主客体比率型荧光探针对尼罗替尼的识别和检测

引用本文: 李孟轩, 殷婷, 肖尊宏, 倪新龙. 十元瓜环主客体比率型荧光探针对尼罗替尼的识别和检测[J]. 分析化学, 2020, 48(12): 1681-1686. doi: 10.19756/j.issn.0253-3820.201084 shu

Citation: LI Meng-Xuan, YIN Ting, XIAO Zun-Hong, NI Xin-Long. Cucurbit[10]uril Host-Guest Based Ratiometric Fluorescent Probe for Recognition of Nilotinib[J]. Chinese Journal of Analytical Chemistry, 2020, 48(12): 1681-1686. doi: 10.19756/j.issn.0253-3820.201084 shu

十元瓜环主客体比率型荧光探针对尼罗替尼的识别和检测

1.
贵州大学贵州省大环化学及超分子化学重点实验室, 贵阳 550025;
2.
贵州师范大学化学与材料科学学院, 贵阳 550025
基金项目:
本文系国家自然科学基金项目（No.21871063）、贵州省科学技术基金项目（No.20165656）和贵州大学自然科学基金项目（Nos.20175788，20185781）资助

摘要: 利用紫外-可见吸收光谱与荧光光谱研究了了十元瓜环（Q[10]）与芘衍生物的主客体作用，并通过量化理论计算了其超分子组装结构。计算结果表明，客体中的芘分子以头碰头的形式从Q[10]的两端反方向平行进入其疏水大空腔，形成2∶1的络合物。等温滴定量热实验结果表明，系列主客体络合反应是焓变驱动。同时，利用芘荧光基团的特征单体/二聚体荧光发射构建了基于Q[10]主客体组装的比率型荧光探针，研究结果表明，此主客体体系在水溶液中对药物分子尼罗替尼具有较好的选择与识别性能，并在一定浓度范围内具有良好的线性关系，检出限为7.05 μmol/L。

关键词:

English

Cucurbit[10]uril Host-Guest Based Ratiometric Fluorescent Probe for Recognition of Nilotinib

1.
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China;
2.
School of Chemistry and Materials, Guizhou Normal University, Guiyang 550025, China
Received Date: 18 February 2020
Revised Date: 28 September 2020
Fund Project:
This work was supported by the National Natural Science Foundation of China (No.21871063) and the Guizhou University (Nos.20175788, 20185781).

Abstract: Host-guest interaction of cucurbit[10]uril (Q[10] or CB[10]) with pyrene-derived derivatives was evaluated by fluorescence emission spectra and UV-vis absorption spectra, and the host-guest binding modes were studied by density functional theory (DFT). In the energy minimization structures, the pyrene group of the guest was encapsulated in the larger hydrophobic cavity of Q[10] in parallel from the opposite direction in the form of a head-to-head fashion, forming a 2∶1 inclusion. The thermodynamic data indicated that the two host-guest interactions were enthalpy-driven. Furthermore, the Q[10] host-guest interaction of Q[10]/G2 could be used as ratiometric fluorescent probe based on the unique monomer/excimer emission of pyrene moiety on the guest G2. Experiment results indicated that the host-guest interaction derived probe had good recognition and selectivity for nilotinib in aqueous solution, and the detection limit was 7.05 μmol/L.

Key words:

1. [1]
  Von B N, Manle P W, Mest J, Sanger J, Pesche C. Blood,2006,108:1328-1333
2. [2]
  FEN Yu-Fei, FU De-Xing. Chin. J. New. Drug, 2008,17 (21):1894-1897 封宇飞, 傅得兴.中国新药杂志,2008,17 (21):1894-1897
3. [3]
  TASIGNA[EB/OI].[2007-12-12].http://www.fda.gov/cder/foi/label/2007/022068lbl.pdf
4. [4]
  4 Ophelia Q P, Gallagher N, Tanaka C, Fisher D, Sethuraman V, Zhou W, Lin T H, Heuman D, Schran H. Clin. Ther.,2009,31:2459-2469
5. [5]
  Pursche S, Ottmann O G, Ehninger G, Schleyerac E. J. Chromatogr. B,2007,852(1-2):208-216
6. [6]
  Deininger M W, McGreevey L, Willi S, Bainbridge T M, Druker B J, Heinrich M C. Leukemia,2004,18:864-871
7. [7]
  Lankheet N A, Hillebrand M J, Rosing H, Schellens J H, Beijnen J H, Huitema A D. Biomed. Chromatogr.,2013,27(4):466-476
8. [8]
  Yilmaz E M, Aydogmuş Z, Aboul-Enein H Y. Acta Chromatogr.,2016,28 (3):313-331
9. [9]
  Ghale G, Nau W M. Acc. Chem. Res., 2014,47(7):2150-2159
10. [10]
  Bai Q H, Zhang S, Chen H, Sun T, Ni X L, Tao Z. ChemistrySelect,2017,2(8):2569-2573
11. [11]
  Day A I, Blanch R J, Arnold A P, Lorenzo S, Lewis G R, Dance I. Angew. Chem. Int. Ed., 2002, 41(2):275-277
12. [12]
  Liu S, Shukla A D, Gadde S, Wagner B D, Kaifer A E, Isaacs L. Angew. Chem. Int. Ed.,2008,47(14):2657-2660
13. [13]
  Kuang S, Hu Z, Zhang H, Zhang X, Liang F, Zhao Z, Liu S. Chem. Commun.,2018,54:2169-2172
14. [14]
  Yang X, Zhao Z, Zhang X, Liu S. Sci. China Chem.,2018,61:787-791
15. [15]
  Zhang W, Luo Y, Zhou Y, Liu M, Xu W, Bian B, Tao Z, Xiao X. Dyes Pigm.,2020,176:108235
16. [16]
  Fan J, Hu M, Zhan P, Peng X. Chem. Soc. Rev.,2013,42:29-43
17. [17]
  YANG Rui-Jie, TANG Yao, ZHU Wei-Ping. Chem. J. Chin. Univ., 2016,37(4):643-647 杨润洁, 唐尧, 朱维平.高等学校化学学报,2016,37(4):643-647
18. [18]
  Figueira-Duarte T M, Müllen K. Chem. Rev., 2011,111(11):7260-7314
19. [19]
  Zhang X, Wu W, Tao Z, Ni X L. Beilstein J. Org. Chem.,2019,15:1705-1711
20. [20]
  Becke A D. J. Chem. Phys., 1992,97(12):9173-9177
21. [21]
  Weigend F, Ahlrichs R. Phys. Chem. Chem. Phys., 2005, 7:3297-3305
22. [22]
  Frisch M J, Trucks G W, Schlegel H B. Gaussian 16, Revision A. 03, Gaussian. Inc. Wallingford CT.,2016
23. [23]
  Freire E, Mayorga O L, Straume M. Anal. Chem.,1990,62(18):950A-959A
24. [24]
  Chaires J B. Annu. Rev. Biophys., 2008,37:135-151

扫一扫看文章

计量

PDF下载量: 24
文章访问数: 855
HTML全文浏览量: 72

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

十元瓜环主客体比率型荧光探针对尼罗替尼的识别和检测

English

Cucurbit[10]uril Host-Guest Based Ratiometric Fluorescent Probe for Recognition of Nilotinib

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

十元瓜环主客体比率型荧光探针对尼罗替尼的识别和检测

English

Cucurbit[10]uril Host-Guest Based Ratiometric Fluorescent Probe for Recognition of Nilotinib

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs