Adsorption of chiral aromatic amino acids onto carboxymethyl-β-cyclodextrin bonded Fe3O4/SiO2 core-shell nanoparticles

被引:168
作者
Ghosh, Sudipa [1 ]
Badruddoza, A. Z. M. [1 ]
Uddin, M. S. [1 ]
Hidajat, K. [1 ]
机构
[1] Natl Univ Singapore, Dept Chem & Biomol Engn, Singapore 117576, Singapore
关键词
Magnetic nanoparticles; Surface functionalization; Carboxymethyl-beta-cyclodextrin; Amino acids; Chiral; Adsorption; COATED NANOMAGNETIC PARTICLES; SEPARATION; POLYMER; MAGNETITE; EXTRACTION; GLYCINE;
D O I
10.1016/j.jcis.2010.11.060
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Surface of magnetic silica nanoparticles is modified by grafting with carboxymethyl-beta-cyclodextrin (CM-beta-CD) via carbodiimide activation. The functionalized magnetic core-shell nanoparticles (MNPs) are characterized by Transmission Electron Microscopy (TEM), Fourier Transform Infra Red (FTIR) spectroscopy, X-ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS) and Vibrating Sample Magnetometer (VSM). These nano-sized particles are scrutinized for adsorption of certain chiral aromatic amino acid enantiomers namely, D- and L-tryptophan (Trp), D- and L-phenylalanine (Phe) and D- and L-tyrosine (Tyr) from phosphate buffer solutions. Adsorption capacities of the coated magnetic nanoparticles toward amino acid enantiomers are in the order: L-Trp > L-Phe > L-Tyr and under the same condition, adsorption capacities are higher for L-enantiomers than the corresponding D-enantiomers. All the equilibrium adsorption isotherms are fitted well to Freundlich model. FTIR studies depict significant changes after adsorption of amino acids onto nanoparticles. The stretching vibration frequencies of N-H bonds of the amino acid molecules are changed with complex formation through host-guest interaction. The structure and hydrophobicity of amino acid molecules emphasize the interactions between amino acid molecules and the nano-adsorbents bearing cyclodextrin, thus play important roles in the difference of their adsorption behaviors. (C) 2010 Elsevier Inc. All rights reserved.
引用
收藏
页码:483 / 492
页数:10
相关论文
共 39 条
[1]   Spectroscopic characterization of Cu(II) complex of L-phenylalanine and D,L-tryptophan [J].
Altun, Oezlen ;
Bilcen, Selin .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2010, 75 (02) :789-793
[2]   SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES [J].
ARMSTRONG, DW ;
WARD, TJ ;
ARMSTRONG, RD ;
BEESLEY, TE .
SCIENCE, 1986, 232 (4754) :1132-1135
[3]   DIRECT LIQUID-CHROMATOGRAPHIC SEPARATION OF RACEMATES WITH AN ALPHA-CYCLODEXTRIN BONDED PHASE [J].
ARMSTRONG, DW ;
YANG, XF ;
HAN, SM ;
MENGES, RA .
ANALYTICAL CHEMISTRY, 1987, 59 (21) :2594-2596
[4]   Highly monodisperse zirconia-coated silica spheres and zirconia/silica hollow spheres with remarkable textural properties [J].
Arnal, Pablo M. ;
Weidenthaler, Claudia ;
Schueth, Ferdi .
CHEMISTRY OF MATERIALS, 2006, 18 (11) :2733-2739
[5]   CHROMATOGRAPHIC DETERMINATION OF D-AMINO ACIDS AS NATIVE CONSTITUENTS OF VEGETABLES AND FRUITS [J].
BRUCKNER, H ;
WESTHAUSER, T .
CHROMATOGRAPHIA, 1994, 39 (7-8) :419-426
[6]   Enantionmer separations in capillary electrophoresis in the case of equal binding constants of the enantiomers with a chiral selector: Commentary on the feasbility of the concept [J].
Chankvetadze, B ;
Lindner, W ;
Scriba, GKE .
ANALYTICAL CHEMISTRY, 2004, 76 (14) :4256-4260
[7]   Synthesis of nickel nanoparticles in water-in-oil microemulsions [J].
Chen, DH ;
Wu, SH .
CHEMISTRY OF MATERIALS, 2000, 12 (05) :1354-1360
[8]   The grafting and release behavior of doxorubincin from Fe3O4@SiO2 core-shell structure nanoparticles via an acid cleaving amide bond:: the potential for magnetic targeting drug delivery [J].
Chen, F. H. ;
Gao, Q. ;
Ni, J. Z. .
NANOTECHNOLOGY, 2008, 19 (16)
[9]   Silane ligand exchange to make hydrophobic superparamagnetic nanoparticles water-dispersible [J].
De Palma, Randy ;
Peeters, Sara ;
Van Bael, Margriet J. ;
Van den Rul, Heidi ;
Bonroy, Kristien ;
Laureyn, Wim ;
Mullens, Jules ;
Borghs, Gustaaf ;
Maes, Guido .
CHEMISTRY OF MATERIALS, 2007, 19 (07) :1821-1831
[10]   On-line selective solid-phase extraction of 4-nitrophenol with β-cyclodextrin bonded silica [J].
Fan, Y ;
Feng, YQ ;
Da, SL .
ANALYTICA CHIMICA ACTA, 2003, 484 (02) :145-153