Synthesis and characterization of β-cyclodextrin/fraxinellone inclusion complex and its influence on interaction with human serum albumin

被引:6
作者
Yan, Jin [1 ]
Tang, Bin [1 ]
Wu, Di [1 ]
Li, Shanshan [1 ]
Xu, Kailin [1 ]
Ma, Xiaoli [1 ]
Wang, Qing [1 ]
Li, Hui [1 ]
机构
[1] Sichuan Univ, Coll Chem Engn, Chengdu 610065, Sichuan, Peoples R China
关键词
beta-cyclodextrin; Fraxinellone; human serum albumin; inclusion complex; spectroscopy; DRUG BINDING-SITES; IMIDAZOLE DERIVATIVES; CYCLODEXTRIN; SPECTROSCOPY; FLUORESCENCE; PHTHALATE; SOLUBILIZATION; FRAXINELLONE; DIFFRACTION; ESTERS;
D O I
10.1080/00387010.2016.1218898
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
Aqueous solubility is one of the key determinants in developing new chemical entities as drugs. In this study, to improve the solubility of fraxinellone, a novel beta-cyclodextrin/ fraxinellone inclusion complex was prepared and characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, X-ray diffraction, and elemental analysis. Moreover, the influence of inclusion of small molecule by cyclodextrins on its binding with transporter in human body is essential for drug development. For the first time, we report the interaction of fraxinellone and its inclusion complex with human serum albumin. Fluorescence quenching of albumin by fraxinellone and its inclusion complex is a static process through complex formation. The results indicated that beta-cyclodextrin did not affect the binding force and site of fraxinellone to the protein. Furthermore, circular dichroism showed that both fraxinellone and its inclusion complex induced a significant change in the secondary structure of human serum albumin.
引用
收藏
页码:542 / 550
页数:9
相关论文
共 47 条
  • [1] The utility of cyclodextrins for enhancing oral bioavailability
    Carrier, Rebecca L.
    Miller, Lee A.
    Ahmed, Mran
    [J]. JOURNAL OF CONTROLLED RELEASE, 2007, 123 (02) : 78 - 99
  • [2] CARTER DC, 1994, ADV PROTEIN CHEM, V45, P153
  • [3] Probing the interactions of hemoglobin with antioxidant flavonoids via fluorescence spectroscopy and molecular modeling studies
    Chaudhuri, Sudip
    Chakraborty, Sandipan
    Sengupta, Pradeep K.
    [J]. BIOPHYSICAL CHEMISTRY, 2011, 154 (01) : 26 - 34
  • [4] Interaction of artemisinin and its derivatives with human serum albumin studied using spectroscopies and molecular modeling methods
    Chen, Rongrong
    Jiang, Hua
    Pu, Hanlin
    [J]. MOLECULAR BIOLOGY REPORTS, 2013, 40 (08) : 4791 - 4804
  • [5] β-Cyclodextrin-dextran polymers for the solubilization of poorly soluble drugs
    di Cagno, Massimiliano
    Nielsen, Thorbjorn Terndrup
    Larsen, Kim Lambertsen
    Kuntsche, Judith
    Bauer-Brandl, Annette
    [J]. INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2014, 468 (1-2) : 258 - 263
  • [6] Characterization of 6-mercaptopurine binding to bovine serum albumin and its displacement from the binding sites by quercetin and rutin
    Ehteshami, Mehdi
    Rasoulzadeh, Farzaneh
    Mahboob, Soltanali
    Rashidi, Mohammad-Reza
    [J]. JOURNAL OF LUMINESCENCE, 2013, 135 : 164 - 169
  • [7] Interaction of cyclodextrins with human and bovine serum albumins: A combined spectroscopic and computational investigation
    Ghosh, Saptarshi
    Paul, Bijan Kumar
    Chattopadhyay, Nitin
    [J]. JOURNAL OF CHEMICAL SCIENCES, 2014, 126 (04) : 931 - 944
  • [8] Novel insights into the pleiotropic effects of human serum albumin in health and disease
    Ha, Chung-Eun
    Bhagavan, Nadhipuram V.
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2013, 1830 (12): : 5486 - 5493
  • [9] Higuchi T., 1965, ADV ANAL CHEM INSTRU, V4, P117, DOI DOI 10.1016/S0076-6879(82)87029-8
  • [10] Site-Selective Binding of Human Serum Albumin by Palmatine: Spectroscopic Approach
    Hu, Yan-Jun
    Ou-Yang, Yu
    Dai, Chun-Mei
    Liu, Yi
    Xiao, Xiao-He
    [J]. BIOMACROMOLECULES, 2010, 11 (01) : 106 - 112