Citation: Liu Nana, Fan Yu, Ma Zhiheng, Lin Haixia, Xu Jiaqiang. Materials design and sensing mechanism of novel calix[6]arene composite for sensitively detecting amine drugs[J]. Chinese Chemical Letters, ;2020, 31(8): 2129-2132. doi: 10.1016/j.cclet.2020.01.034 shu

Materials design and sensing mechanism of novel calix[6]arene composite for sensitively detecting amine drugs

Liu Nana ^a ,
Fan Yu ^b ,
Ma Zhiheng ^b ,
Lin Haixia ^a,*, ,
Xu Jiaqiang ^a,*,

a.
NEST Lab, Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444, China
b.
Department of Physics, College of Science, Shanghai University, Shanghai 200444, China

haixialin@staff.shu.edu.cn

xujiaqiang@shu.edu.cn

Received Date: 19 December 2019
Revised Date: 12 January 2020
Accepted Date: 13 January 2020
Available Online: 17 January 2020

Figures(9)

In order to improve the convenience and sensitivity of amphetamines drug testing and reduce the threat of drugs to humans, we have designed a QCM gas sensor to detect amine-containing drugs. The sensing material is designed based on the chemical nature of amine drugs. The sensing mechanism is derived from a reversible Schiff base interaction between the amino group of the drug and the carbonyl group of the novel calix[6]arene derivatives as well as the hydrogen bond interaction between amino group and hydroxyl. The new composite material was well characterized by different analytical techniques including ¹H nuclear magnetic resonance (¹H-NMR), fourier transform infrared spectroscopy (FT-IR), scanning electronic microscopy (SEM), transmission electron microscope (TEM), Raman spectra, powder X-ray diffraction, etc. The sensing experiments were conducted by coating the composite onto quartz crystal microbalance (QCM) transducers. The experimental results indicated that the novel calixarene derivatives and their GO complexes based on the design have excellent selectivity, high sensitivity and repeatability to β-phenylethylamine.
- Drug detection,
- Calix[6]arene derivative,
- GO complexes,
- Quartz crystal microbalance sensor,
- Schiff base interaction
1. [1]
  Y. Lv, H. Yu, P. Xu, J. Xu, X. Li, Sensor. Actuat. B-Chem. 256(2018) 639-647. doi: 10.1016/j.snb.2017.09.195
2. [2]
  R. Toniolo, A. Pizzariello, N. Dossi, et al., Anal. Chem. 85(2013) 7241-7247. doi: 10.1021/ac401151m
3. [3]
  Y. Zhu, Z. Cheng, Q. Xiang, Y. Zhu, J. Xu, Sensor. Actuat. B-Chem. 256(2018) 888-895. doi: 10.1016/j.snb.2017.10.029
4. [4]
  Y. Lu, S. Song, C. Hou, et al., Chin. Chem. Lett. 29(2018) 65-68. doi: 10.1016/j.cclet.2017.08.003
5. [5]
  H. Wang, X. Liu, J. Xie, M. Duan, J. Tang, Chin. Chem. Lett. 27(2016) 464-466. doi: 10.1016/j.cclet.2015.12.027
6. [6]
  L. Wang, Y. Yu, Q. Xiang, et al., Sensor. Actuat. B-Chem. 255(2018) 2704-2712. doi: 10.1016/j.snb.2017.09.082
7. [7]
  Z. Duan, Y. Jiang, M. Yan, et al., ACS Appl. Mater. Interfaces 11(2019) 21840-21849. doi: 10.1021/acsami.9b05709
8. [8]
  S. Wang, G. Xie, Y. Su, et al., Sensor. Actuat. B-Chem. 255(2018) 2203-2210. doi: 10.1016/j.snb.2017.09.028
9. [9]
  D. Battal, S. Akgonullu, M.S. Yalcin, et al., Biosens. Bioelectron.111(2018) 10-17. doi: 10.1016/j.bios.2018.03.055
10. [10]
  L. Wang, Y. Zhu, Q. Xiang, et al., Sensor. Actuat. B-Chem. 251(2017) 590-600. doi: 10.1016/j.snb.2017.05.074
11. [11]
  L. Wang, X. Cha, Y. Wu, et al., ACS Omega 3(2018) 2437-2443. doi: 10.1021/acsomega.8b00061
12. [12]
  L. Wang, J. Gao, J. Xu, Sensor. Actuat. B-Chem. 293(2019) 71-82. doi: 10.1016/j.snb.2019.04.050
13. [13]
  L. Wang, Z. Wang, Q. Xiang, et al., Sensor. Actuat. B-Chem. 248(2017) 820-828. doi: 10.1016/j.snb.2016.12.015
14. [14]
  W. Chen, F. Deng, M. Xu, et al., Sensor. Actuat. B-Chem. 273(2018) 498-504. doi: 10.1016/j.snb.2018.06.062
15. [15]
  M.M. Ayad, N.L. Torad, Sensor. Actuat. B-Chem. 147(2010) 481-487. doi: 10.1016/j.snb.2010.03.064
16. [16]
  K. Zhang, R. Hu, G. Fan, et al., Sensor. Actuat. B-Chem. 243(2017) 721-730. doi: 10.1016/j.snb.2016.12.063
17. [17]
  F. Temel, S. Erdemir, B. Tabakci, et al., Anal. Bioanal. Chem. 411(2019) 2675-2685. doi: 10.1007/s00216-019-01705-5
18. [18]
  Y. Liu, Z. Zhong, J. Macromol. Sci. Part A 54(2017) 678-683. doi: 10.1080/10601325.2017.1321959
19. [19]
  D.S. Guo, Y. Liu, Chem. Soc. Rev. 41(2012) 5907-5921. doi: 10.1039/c2cs35075k
20. [20]
  R.K. Castellano, D.M. Rudkevich, J. Julius Rebek, Nat. Acad. Sci. 94(1997) 7132-7137. doi: 10.1073/pnas.94.14.7132
21. [21]
  J. Rebek Jr, Chem. Commun. (2000) 637-643. doi: 10.1039/A910339M
22. [22]
  D.M.H.A.C. Redshaw, Chem. Rev. 108(2008) 5086-5130. doi: 10.1021/cr8002196
23. [23]
  D.R. Dreyer, S. Park, C.W. Bielawski, et al., Chem. Soc. Rev. 39(2010) 228-240. doi: 10.1039/B917103G
24. [24]
  M. Hirata, T. Gotou, S. Horiuchi, et al., Carbon 42(2004) 2929-2937. doi: 10.1016/j.carbon.2004.07.003
25. [25]
  N.I. Zaaba, K.L. Foo, U. Hashim, et al., Proc. Engin. 184(2017) 469-477. doi: 10.1016/j.proeng.2017.04.118
26. [26]
  I.A. Koshets, Z.I. Kazantseva, Y.M. Shirshov, et al., Sensor. Actuat. B-Chem. 106(2005) 177-181. doi: 10.1016/j.snb.2004.05.054
27. [27]
  J.H. Wosnick, T.M. Swager, Chem. Commun. (2004) 2744-2745. doi: 10.1039/b411489b
28. [28]
  M. Namba, M. Sugawara, P. Buhlmann, et al., Am. Chem. Soc. 11(1995) 635-638. doi: 10.1023/A:1021373400660
29. [29]
  A. Ganguly, S. Sharma, P. Papakonstantinou, et al., J. Phys. Chem. C 115(2011) 17009-17019. doi: 10.1021/jp203741y
30. [30]
  E. Valeur, M. Bradley, Chem. Soc. Rev. 38(2009) 606-631. doi: 10.1039/B701677H
31. [31]
  C.L. Aronson, D. Beloskur, I.S. Frampton, et al., Polym. Bull. 52(2004) 409-419. doi: 10.1007/s00289-004-0305-x
32. [32]
  S. Ren, Z. Wu, Q. Guo, B. Shen, Catal. Lett. 145(2014) 712-714.
1. [1]
  Xiaofen GUAN , Yating LIU , Jia LI , Yiwen HU , Haiyuan DING , Yuanjing SHI , Zhiqiang WANG , Wenmin WANG . Synthesis, crystal structure, and DNA-binding of binuclear lanthanide complexes based on a multidentate Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2486-2496. doi: 10.11862/CJIC.20240122
2. [2]
  Tao Yu , Vadim A. Soloshonok , Zhekai Xiao , Hong Liu , Jiang Wang . Probing the dynamic thermodynamic resolution and biological activity of Cu(Ⅱ) and Pd(Ⅱ) complexes with Schiff base ligand derived from proline. Chinese Chemical Letters, 2024, 35(4): 108901-. doi: 10.1016/j.cclet.2023.108901
3. [3]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
4. [4]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
5. [5]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
6. [6]
  Xiangshuai Li , Jian Zhao , Li Luo , Zhuohao Jiao , Ying Shi , Shengli Hou , Bin Zhao . Visual and portable detection of metronidazole realized by metal-organic framework flexible sensor and smartphone scanning. Chinese Chemical Letters, 2024, 35(10): 109407-. doi: 10.1016/j.cclet.2023.109407
7. [7]
  Xiaofei NIU , Ke WANG , Fengyan SONG , Shuyan YU . Self-assembly of [Pd₆(L)₄]⁸⁺-type macrocyclic complexes for fluorescent sensing of HSO₃^-. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1233-1242. doi: 10.11862/CJIC.20240057
8. [8]
  Shengwen Guan , Zhaotong Wei , Ningxu Han , Yude Wei , Bin Xu , Ming Wang , Junjuan Shi . Construction of metallo-complexes with 2,2′:6′,2″-terpyridine substituted triphenylamine in different modified positions and their photophysical properties. Chinese Chemical Letters, 2024, 35(7): 109348-. doi: 10.1016/j.cclet.2023.109348
9. [9]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
10. [10]
  Linghui Zou , Meng Cheng , Kaili Hu , Jianfang Feng , Liangxing Tu . Vesicular drug delivery systems for oral absorption enhancement. Chinese Chemical Letters, 2024, 35(7): 109129-. doi: 10.1016/j.cclet.2023.109129
11. [11]
  Fengjie Liu , Fansu Meng , Zhenjiang Yang , Huan Wang , Yuehong Ren , Yu Cai , Xingwang Zhang . Exosome-biomimetic nanocarriers for oral drug delivery. Chinese Chemical Letters, 2024, 35(9): 109335-. doi: 10.1016/j.cclet.2023.109335
12. [12]
  Haodong Wang , Xiaoxu Lai , Chi Chen , Pei Shi , Houzhao Wan , Hao Wang , Xingguang Chen , Dan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473
13. [13]
  Zhibin Ren , Shan Li , Xiaoying Liu , Guanghao Lv , Lei Chen , Jingli Wang , Xingyi Li , Jiaqing Wang . Penetrating efficiency of supramolecular hydrogel eye drops: Electrostatic interaction surpasses ligand-receptor interaction. Chinese Chemical Letters, 2024, 35(11): 109629-. doi: 10.1016/j.cclet.2024.109629
14. [14]
  Yujie Li , Ya-Nan Wang , Yin-Gen Luo , Hongcai Yang , Jinrui Ren , Xiao Li . Advances in synthetic biology-based drug delivery systems for disease treatment. Chinese Chemical Letters, 2024, 35(11): 109576-. doi: 10.1016/j.cclet.2024.109576
15. [15]
  Shaoqing Du , Xinyong Liu , Xueping Hu , Peng Zhan . Targeting novel sites represents an effective strategy for combating drug resistance. Chinese Chemical Letters, 2025, 36(1): 110378-. doi: 10.1016/j.cclet.2024.110378
16. [16]
  Cheng Wang , Ji Wang , Dong Liu , Zhi-Ling Zhang . Advances in virus-host interaction research based on microfluidic platforms. Chinese Chemical Letters, 2024, 35(12): 110302-. doi: 10.1016/j.cclet.2024.110302
17. [17]
  Yadan SUN , Xinfeng LI , Qiang LIU , Oshio Hiroki , Yinshan MENG . Structures and magnetism of dinuclear Co complexes based on imine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2212-2220. doi: 10.11862/CJIC.20240131
18. [18]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
19. [19]
  Zihong Li , Jie Cheng , Ping Huang , Guoliang Wu , Weiying Lin . Activatable photoacoustic bioprobe for visual detection of aging in vivo. Chinese Chemical Letters, 2024, 35(4): 109153-. doi: 10.1016/j.cclet.2023.109153
20. [20]
  Ningyue Xu , Jun Wang , Lei Liu , Changyang Gong . Injectable hydrogel-based drug delivery systems for enhancing the efficacy of radiation therapy: A review of recent advances. Chinese Chemical Letters, 2024, 35(8): 109225-. doi: 10.1016/j.cclet.2023.109225

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(652)
HTML views(57)

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