Citation: Wei Sun, Zhao-Hui Wang, Meng-Yao She, Zheng Yang, Xi-Lang Jin, Ya-Qi Wang, Zhen Shi, Jian-Li Li. Study on the inclusion behavior and solid inclusion complex of 5-amino-6-methyl-2-benzimidazolone with cyclodextrins[J]. Chinese Chemical Letters, ;2016, 27(7): 1077-1082. doi: 10.1016/j.cclet.2016.03.009 shu

Study on the inclusion behavior and solid inclusion complex of 5-amino-6-methyl-2-benzimidazolone with cyclodextrins

  • Corresponding author: Jian-Li Li, lijianli@nwu.edu.cn
  • Received Date: 23 November 2015
    Revised Date: 2 March 2016
    Accepted Date: 4 March 2016
    Available Online: 16 July 2016

Figures(6)

  • The inclusion behaviors of three native or modified CDs including β-CD, 2-hydroxypropyl-β-CD (2-Hp-β-CD) and 2, 6-dimethyl-β-CD (Me-β-CD) toward 5-amino-6-methyl-2-benzimidazolone (AMBI) were comparatively investigated by NMR and fluorescence titration in combination with IR spectra, X-ray diffractometry and scanning electron microphotographs. The experimental results jointly demonstrated that the phenyl ring of AMBI entered into the cavity of the CDs and located close to the narrow rims accompanied by the formation of the 1:1 inclusion complex with large stability constant in aqueous solution. The introduction of the hydroxypropyl unit to the host improved the solubility, ultimately effecting an obvious promoting in the fluorescence intensity and the stability constant.
  • 加载中
    1. [1]

      (a) X. Ma, Y.L. Zhao, Biomedical applications of supramolecular systems based on host-guest interactions, Chem. Rev. 115 (2015) 7794-7839;

    2. [2]

      (b) A. Harada, Y. Takashima, M. Nakahata, Supramolecular polymeric materials via cyclodextrin-guest interactions, Acc. Chem. Res. 47 (2014) 2128-2140.

    3. [3]

      (a) J.X. Zhang, P.X. Ma, Cyclodextrin-based supramolecular systems for drug delivery: recent progress and future perspective, Adv. Drug Deliv. Rev. 65 (2013) 1215-1233;

    4. [4]

      J. Szejtli. Introduction and general overview of cyclodextrin chemistry[J]. Chem. Rev., 1998,98:1743-1754. doi: 10.1021/cr970022c

    5. [5]

      L. Szente, J. Szemá n. Cyclodextrins in analytical chemistry: host-guest type molecular recognition[J]. Anal. Chem., 2013,85:8024-8030. doi: 10.1021/ac400639y

    6. [6]

      K.A. Connors. The stability of cyclodextrin complexes in solution[J]. Chem. Rev., 1997,97:1325-1358. doi: 10.1021/cr960371r

    7. [7]

      (b) G. Ghale, W.M. Nau, Dynamically analyte-responsive macrocyclic host-fluorophore systems, Acc. Chem. Res. 47 (2014) 2150-2159.

    8. [8]

      J. Szejtli, Introduction and general overview of cyclodextrin chemistry, Chem. Rev. 98 (1998) 1743-1754.

    9. [9]

      L. Szente, J. Szemá n, Cyclodextrins in analytical chemistry: host-guest type molecular recognition, Anal. Chem. 85 (2013) 8024-8030.

    10. [10]

      K.A. Connors, The stability of cyclodextrin complexes in solution, Chem. Rev. 97 (1997) 1325-1358.

    11. [11]

      (a) S.M.N. Simões, A. Rey-Rico, A. Concheiro, C. Alvarez-Lorenzo, Supramolecular cyclodextrin-based drug nanocarriers, Chem. Commun. 51 (2015) 6275-6289;

    12. [12]

      (b) Y. Chen, Y. Liu, Cyclodextrin-based bioactive supramolecular assemblies, Chem. Soc. Rev. 39 (2010) 495-505;

    13. [13]

      D. Zhao, Y. Chen, Y. Liu. Comparative studies on molecular induced aggregation of hepta-imidazoliumyl-β-cyclodextrin towards anionic surfactants[J]. Chin. Chem. Lett., 2015,26:829-833. doi: 10.1016/j.cclet.2014.11.028

    14. [14]

      S.S. Zhai, Y. Chen, Y. Liu. Selective binding of bile salts by β-cyclodextrin derivatives with appended quinolyl arms[J]. Chin. Chem. Lett., 2013,24:442-446. doi: 10.1016/j.cclet.2013.04.008

    15. [15]

      C.H. Diao, Z. Xu, M.J. Guo. , The structural analysis of the inclusion complex of β-cyclodextrin with m-nitrophenoxyacetic acid[J]. Chin. Chem. Lett., 2013,24:487-490. doi: 10.1016/j.cclet.2013.03.047

  • 加载中
    1. [1]

      Kai Jun LIAO Xiao Hua YAN Dong Yun ZHAO Xue Yi MA . DSC and NMR Study on the Inclusion Complex of Lappaconitine with β-Cyclodextrin. Chinese Chemical Letters, 2002, 13(3): 227-230.

    2. [2]

      Xue Yi MA Zhi Xin LIAO Yun ZEN Hua Dong XIU Ru LIU Yao Zu CHEN . X-Ray Diffraction and NMR Study of Inclusion Complex of Podophyllotoxin with β-Cyclodextrin. Chinese Chemical Letters, 1999, 10(4): 313-316.

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      Dong Yu ZHAO Sheng Hua YANG Ming HU Xue Yi MA . Structural Study of Inclusion Complex of Andrographolide with β-Cyclodextrin Prepared under Microwave Irradiation. Chinese Chemical Letters, 2003, 14(2): 155-158.

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    5. [5]

      Li-Hua WangZhi-Jun ZhangHeng-Yi ZhangHai-Lang WuYu Liu . A twin-axial[5]pseudorotaxane based on cucurbit[8]uril and a-cyclodextrin. Chinese Chemical Letters, 2013, 24(11): 949-952.

    6. [6]

      Di ZhaoYong ChenYu Liu . Comparative studies on molecular induced aggregation of hepta-imidazoliumyl-β-cyclodextrin towards anionic surfactants. Chinese Chemical Letters, 2015, 26(7): 829-833. doi: 10.1016/j.cclet.2014.11.028

    7. [7]

      Cui Ping Han Hai Bing Li . Novel β-cyclodextrin modified quantum dots as fluorescent probes for polycyclic aromatic hydrocarbons (PAHs). Chinese Chemical Letters, 2008, 19(2): 215-218. doi: 10.1016/j.cclet.2007.11.008

    8. [8]

      Jing HU Cheng Feng YE Yong De ZHAO Jun Biao CHANG Rui Yun GUO . A Facile Synthesis of β-Cyclodextrin Monoaldehyde. Chinese Chemical Letters, 1999, 10(4): 273-274.

    9. [9]

      Xiao Ping Chen Zhi Ming Zhou Hao Yuan Zi Hui Meng . Preparation and chiral recognition of a novel chiral stationary phase for HPLC,based on mono(6A-N-1-(2-hydroxyl)-phenylethylimino-6A-deoxy)-β-cyclodextrin and covalently bonded silica gel. Chinese Chemical Letters, 2008, 19(7): 797-800. doi: 10.1016/j.cclet.2008.04.045

    10. [10]

      Xian Hong YIN . Synthesis of Terpyridine Derivatives Containing β-Cyclodextrin. Chinese Chemical Letters, 2003, 14(5): 445-447.

    11. [11]

      Zheng Ning LI Xiu Mei LIU Zhuo ZHENG Hui Lin CHEN Xiu Wen HAN . NMR Studies of 3-Acylcamphor. Chinese Chemical Letters, 2000, 11(3): 259-260.

    12. [12]

      Jian Liang YE Xing Wang ZHOU Zhong CHEN Zhi Wei CHEN Pei Qiang HUANG . Studies on the Interactions between Potassium oxalato oxodiperoxovanadate and Histidine by NMR and MS. Chinese Chemical Letters, 2001, 12(11): 987-988.

    13. [13]

      Nida N. Farshori Mudasir R. Banday Zeeshan Zahoor Abdul Rauf . DCC/DMAP mediated esterification of hydroxy and non-hydroxy olefinic fatty acids with β-sitosterol: In vitro antimicrobial activity. Chinese Chemical Letters, 2010, 21(6): 646-650. doi: 10.1016/j.cclet.2010.01.003

    14. [14]

      Song ChunxiaXiao YuxinLi KunpengZhang XiaoyuLu Yingβ-Cyclodextrin polymer based fluorescence enhancement method for sensitive adenosine triphosphate detection. Chinese Chemical Letters, 2019, 30(6): 1249-1252. doi: 10.1016/j.cclet.2019.03.055

    15. [15]

      Dong Jun WANG Dan Dan JIA Yong Guang ZHAO Xi Hai SHEN Yue Dong YANG . Fluorescence Emission from Small Molecules Containing Amino Group. Chinese Chemical Letters, 2006, 17(4): 502-504.

    16. [16]

      Yong Nian Ni Xue Zhi Zhong . Investigation of the interaction of DNA and neutral red by fluorescence spectroscopic analysis. Chinese Chemical Letters, 2007, 18(5): 569-572. doi: 10.1016/j.cclet.2007.03.027

    17. [17]

      Yang ZhiyongHu JiehanLiu XiumeiYang Zhenyun . SYNTHESES AND NMR STUDIES OF POLYDENTATE PLATINUM COMPLEXES. Chinese Journal of Applied Chemistry, 1992, 9(5): 44-49.

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    20. [20]

      Yu Zhang Shang Wen Yan Gong Lu Jin Shuang Man Li Zhong Ping Chen Ming Ma Ning Gu . Magnetic nanocomposites of Fe3O4/SiO2-FITC with pH-dependent fluorescence emission. Chinese Chemical Letters, 2009, 20(8): 969-972. doi: 10.1016/j.cclet.2009.03.038

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