Study on Host-Guest Inclusion Complexation of a Drug in Cucurbit [6]uril

Abstract Assembly of pyridine-2-aldoxime drug with cucurbit [6]uril (CB[6]) has been investigated by 1H-NMR and 2D-ROESY NMR, UV-Vis spectroscopy, FT-IR spectroscopy, surface tension and conductivity measurements in aqueous saline environment. The distinct cationic receptor feature and the cavity dimension of the CB[6] emphasize that the macro-cyclic host molecule remain as complex with the nerve stimulus drug molecule. The results obtained from surface tension and specific conductivity measurements suggest 1:1 inclusion complex formation between drug and CB[6]. The stability constant evaluated by UV-Vis spectroscopic approach is 2.21×105 M−1 at 298.15 K, which indicates that the complex is sufficiently stable at physiological temperature.

[1]  M. Roy,et al.  Probing inclusion complexes of cyclodextrins with amino acids by physicochemical approach. , 2016, Carbohydrate polymers.

[2]  Wei Li,et al.  The Adsorption of Reactive Blue 19 Dye onto Cucurbit[8]uril and Cucurbit[6]uril: An Experimental and Theoretical Study. , 2016, The journal of physical chemistry. B.

[3]  Shengke Li,et al.  Supramolecular encapsulation of benzocaine and its metabolite para-aminobenzoic acid by cucurbit[7]uril , 2016 .

[4]  Kanak Roy,et al.  Self-assembly inclusion of green solvent with oligosaccharides , 2016 .

[5]  M. Roy,et al.  Host–guest inclusion complexes of RNA nucleosides inside aqueous cyclodextrins explored by physicochemical and spectroscopic methods , 2016 .

[6]  M. Roy,et al.  NMR, surface tension and conductivity studies to determine the inclusion mechanism: thermodynamics of host–guest inclusion complexes of natural amino acids in aqueous cyclodextrins , 2016 .

[7]  Kanak Roy,et al.  Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions , 2015 .

[8]  M. Roy,et al.  Host–guest inclusion complexes of α and β-cyclodextrins with α-amino acids , 2014 .

[9]  N. Wheate,et al.  Chemical factors affecting cucurbit[n]uril formulation into ocular dosage forms: excipient binding, solubility, corneal permeability and antibiotic encapsulation , 2014 .

[10]  V. Aswal,et al.  Stimuli-responsive supramolecular micellar assemblies of cetylpyridinium chloride with cucurbit[5/7]urils. , 2014, Soft matter.

[11]  Y. Ko,et al.  Cucurbit[7]uril: a high-affinity host for encapsulation of amino saccharides and supramolecular stabilization of their α-anomers in water. , 2014, Angewandte Chemie.

[12]  L. Isaacs,et al.  Cucurbit[7]uril containers for targeted delivery of oxaliplatin to cancer cells. , 2013, Angewandte Chemie.

[13]  D. B. Collum,et al.  Method of continuous variations: applications of job plots to the study of molecular associations in organometallic chemistry. , 2013, Angewandte Chemie.

[14]  Yuan Chen,et al.  Structural interrogation of a cucurbit[7]uril-ferrocene host–guest complex in the solid state: a Raman spectroscopy study , 2013 .

[15]  Hao Wang,et al.  Supramolecular vesicle: triggered by formation of pseudorotaxane between cucurbit[6]uril and surfactant. , 2011, Chemical communications.

[16]  C. Park,et al.  Facile, template-free synthesis of stimuli-responsive polymer nanocapsules for targeted drug delivery. , 2010, Angewandte Chemie.

[17]  S. P. Gejji,et al.  Density functional investigations on the charge distribution, vibrational spectra, and NMR chemical shifts in cucurbit[n]uril (n = 5-12) hosts. , 2010, Journal of Physical Chemistry A.

[18]  M. Prostran,et al.  Pyridinium oximes as cholinesterase reactivators. Structure-activity relationship and efficacy in the treatment of poisoning with organophosphorus compounds. , 2009, Current medicinal chemistry.

[19]  Yu Liu,et al.  Cyclodextrin-driven movement of cucurbit[7]uril. , 2007, The Journal of organic chemistry.

[20]  Young Ho Ko,et al.  Functionalized cucurbiturils and their applications. , 2007, Chemical Society reviews.

[21]  Shaohua Zhang,et al.  Inclusion Complexes of β-Cyclodextrin with Ionic Liquid Surfactants , 2006 .

[22]  A. Kaifer,et al.  Modes of binding interaction between viologen guests and the cucurbit[7]uril host. , 2004, Organic Letters.

[23]  Jae Wook Lee,et al.  Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. , 2003, Accounts of chemical research.

[24]  Kimoon Kim Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. , 2002, Chemical Society reviews.

[25]  R. Nolte,et al.  Self-assembled Architectures from Glycoluril , 2000 .

[26]  P. Ashton,et al.  Molecular Necklace: Quantitative Self-Assembly of a Cyclic Oligorotaxane from Nine Molecules , 1998 .

[27]  Jean-Marie Lehn,et al.  Comprehensive Supramolecular Chemistry , 1996 .

[28]  W. L. Mock,et al.  Structure and selectivity in host―guest complexes of cucurbituril , 1986 .

[29]  J. Lehn,et al.  Supramolecular Chemistry: Receptors, Catalysts, and Carriers , 1985, Science.

[30]  W. L. Mock,et al.  Host-guest binding capacity of cucurbituril , 1983 .

[31]  D. Grob,et al.  Poisoning due to organophosphate insecticides. Acute and chronic manifestations. , 1971, The American journal of medicine.

[32]  Joel H. Hildebrand,et al.  A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons , 1949 .