Effect of the chiral discrimination on the vibrational properties of (R)-, (S)- and (R, S)-ibuprofen/methyl-β-cyclodextrin inclusion complexes

被引：13
|
作者：
Crupi, V. [1 ,2 ]
Guella, G. [3 ]
Majolino, D. [1 ,2 ]
Mancini, I. [3 ]
Paciaroni, A. [4 ,5 ]
Rossi, B. [3 ,6 ]
Venuti, V. [1 ,2 ]
Verrocchio, P. [3 ]
Viliani, G. [3 ]
机构：
[1] Univ Messina, Dipartimento Fis, I-98166 Messina, Italy
[2] CNISM, I-98166 Messina, Italy
[3] Univ Trento, Dipartimento Fis, I-38123 Povo, Trento, Italy
[4] Univ Perugia, Dipartimento Fis, CEMIN, I-06123 Perugia, Italy
[5] INFM CRS SOFT, I-06123 Perugia, Italy
[6] Fdn Bruno Kessler, I-38123 Povo, Trento, Italy
来源：
PHILOSOPHICAL MAGAZINE | 2011年 / 91卷 / 13-15期
关键词：
ibuprofen; inclusion complex; FTIR-ATR spectroscopy; numerical simulation; chirality; CAPILLARY-ELECTROPHORESIS; IBUPROFEN; ENANTIOMERS; SEPARATION; NAPROXEN; ISOMERS; DRUGS;
D O I：
10.1080/14786435.2010.512575
中图分类号：
T [工业技术];
学科分类号：
08 ;
摘要：
The effects of chiral discrimination of ibuprofen (IBP) on the complexation process with methyl-beta-cyclodextrin (Me-beta-CD) were investigated in the solid phase by FTIR-ATR spectroscopy and numerical simulation. The inclusion mechanism was deduced from the temperature-dependent analysis of the vibrational spectra, in the C=O stretching region, of complexes formed by Me-beta-CD with the two enantiomeric and the racemic forms of IBP. The mechanism turned out to be enthalpy-driven, with IBP enantiomers giving rise to more stable inclusion complexes with respect to the racemate.
引用
收藏
页码：1776 / 1785
页数：10
相关论文
共 50 条
  • [21] Polymeric stationary phase, based on (R,R)-tartramide and bisphenol S, with potential chiral properties
    Jablonska-Pikus, T
    Charmas, W
    Podkoscielna, B
    Gawdzik, B
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (10) : 2566 - 2574
  • [22] Excited-state chiral discrimination of Tb(III) complexes of (S,S′)- and (R,R′)-ethylenediamine-N,N′-disuccinic acid in circularly polarized luminescence and luminescence decay profiles
    Morita, M
    Herren, M
    Ansai, T
    Rau, D
    JOURNAL OF LUMINESCENCE, 2000, 87-9 : 976 - 979
  • [23] (R)- and (S)-enantioselective lithiation of (arene)tricarbonylchromium acetal complexes with chiral alkyllithiums
    Siwek, MJ
    Green, JR
    CHEMICAL COMMUNICATIONS, 1996, (20) : 2359 - 2360
  • [24] Efficient enantioconvergent synthesis of (S)-α-benzyl-α-methyl-β-alanine from (R)- and (S)-2-cyano-2-methyl-3-phenylpropanoic acid
    Badorrey, R
    Cativiela, C
    Díaz-De-Villegas, MD
    Gálvez, JA
    Gil, A
    TETRAHEDRON-ASYMMETRY, 2003, 14 (15) : 2209 - 2214
  • [25] Chiral discrimination in electrocatalytic oxidation of (R)- and (S)-1-phenylethanol usinga chiral nitroxyl radical as catalyst
    Kashiwagi, Y
    Uchiyama, K
    Kurashima, F
    Kikuchi, C
    Anzai, J
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (07) : 1051 - 1052
  • [26] Enantioselective Toxicity of Ibuprofen to Earthworms: Unraveling the Effect and Mechanism on Enhanced Toxicity of S-Ibuprofen Over R-Ibuprofen
    Jiang, Wenqi
    Zhao, Zeyu
    Zhao, Qi
    He, Xiwei
    Chen, Haonan
    Wu, Gang
    Zhang, Xu-Xiang
    ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2024, 59 (01) : 756 - 766
  • [27] Determination of the enantiomeric purity of S-ropivacaine by capillary electrophoresis with methyl-β-cyclodextrin as chiral selector using conventional and complete filling techniques
    Amini, A
    Wiersma, B
    Westerlund, D
    Paulsen-Sörman, U
    EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 1999, 9 (01) : 17 - 24
  • [28] Study of the inclusion of the (R)- and (S)-camphor enantiomers in α-cyclodextrin by X-ray crystallography and molecular dynamics
    Kokkinou, Areti
    Tsorteki, Frantzeska
    Karpusas, Michael
    Papakyriakou, Athanasios
    Bethanis, Kostas
    Mentzafos, Dimitris
    CARBOHYDRATE RESEARCH, 2010, 345 (08) : 1034 - 1040
  • [29] Validated Densitometric TLC Method for Analysis of (R)- and (S)-Bupivacaine, Using Cyclodextrin Derivatives as Chiral Selectors
    Salama, Nahla Nour El-Din Ahmed
    JPC-JOURNAL OF PLANAR CHROMATOGRAPHY-MODERN TLC, 2008, 21 (06) : 441 - 446
  • [30] Theoretical investigations of free energy of binding and chiral recognition studies of (R)- and (S)-Noradrenaline towards β-cyclodextrin
    Karthikeyan, Murugesan
    Kumar, Marimuthu Dhinesh
    Kaniraja, Ganesan
    Karunakaran, Chandran
    JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2023, 124
12345