Abstract
The molecular recognition behaviors of some representative bile salts by three 3,6-bridged β-cyclodextrin dimers with oligo(ethylenediamino) linkers in different lengths, i.e. 3,6-(ethylenediamino-bridged) β-cyclodextrin dimer (1), 3,6-(diethylenetriamino-bridged) β-cyclodextrin dimer (2), and 3,6-(triethylenetetraamino-bridged) β-cyclodextrin dimer (3), were investigated in aqueous phosphate buffer solution (pH 7.20) at 25°C by means of 2D NMR spectroscopy and isothermal titration microcalorimetry. Owing to the cooperative host-linker-guest binding mode between host and guest, these 3,6-bridged β-cyclodextrin dimers showed significantly enhanced binding abilities and molecular selectivities as compared with native β-cyclodextrin through the simultaneous contributions of hydrophobic, hydrogen bond, and electrostatic interactions. Thermodynamically, the inclusion complexations of these β-cyclodextrin dimers with bile salts were mainly driven by large enthalpic gain, accompanied by slight to moderate entropic loss. An enthalpy-entropy compensation analysis demonstrated that these β-cyclodextrin dimers experienced large conformational changes and extensive desolvation effect upon inclusion complexation with guest molecules.
Keywords: Cyclodextrin, bile salt, calorimetry, inclusion phenomena, synthetic receptors, host-guest modeling systems, molecular recognition, thermodynamics
Combinatorial Chemistry & High Throughput Screening
Title: Thermodynamics of Molecular Recognition of Bile Salts by 3,6- (Oligoethylenediamino-Bridged) β-Cyclodextrin Dimers
Volume: 10 Issue: 5
Author(s): Yu Liu, Shu Kang, Yong Chen, Rui Cao and Jun Shi
Affiliation:
Keywords: Cyclodextrin, bile salt, calorimetry, inclusion phenomena, synthetic receptors, host-guest modeling systems, molecular recognition, thermodynamics
Abstract: The molecular recognition behaviors of some representative bile salts by three 3,6-bridged β-cyclodextrin dimers with oligo(ethylenediamino) linkers in different lengths, i.e. 3,6-(ethylenediamino-bridged) β-cyclodextrin dimer (1), 3,6-(diethylenetriamino-bridged) β-cyclodextrin dimer (2), and 3,6-(triethylenetetraamino-bridged) β-cyclodextrin dimer (3), were investigated in aqueous phosphate buffer solution (pH 7.20) at 25°C by means of 2D NMR spectroscopy and isothermal titration microcalorimetry. Owing to the cooperative host-linker-guest binding mode between host and guest, these 3,6-bridged β-cyclodextrin dimers showed significantly enhanced binding abilities and molecular selectivities as compared with native β-cyclodextrin through the simultaneous contributions of hydrophobic, hydrogen bond, and electrostatic interactions. Thermodynamically, the inclusion complexations of these β-cyclodextrin dimers with bile salts were mainly driven by large enthalpic gain, accompanied by slight to moderate entropic loss. An enthalpy-entropy compensation analysis demonstrated that these β-cyclodextrin dimers experienced large conformational changes and extensive desolvation effect upon inclusion complexation with guest molecules.
Export Options
About this article
Cite this article as:
Liu Yu, Kang Shu, Chen Yong, Cao Rui and Shi Jun, Thermodynamics of Molecular Recognition of Bile Salts by 3,6- (Oligoethylenediamino-Bridged) β-Cyclodextrin Dimers, Combinatorial Chemistry & High Throughput Screening 2007; 10 (5) . https://dx.doi.org/10.2174/138620707781662844
DOI https://dx.doi.org/10.2174/138620707781662844 |
Print ISSN 1386-2073 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5402 |
Call for Papers in Thematic Issues
Artificial Intelligence Methods for Biomedical, Biochemical and Bioinformatics Problems
Recently, a large number of technologies based on artificial intelligence have been developed and applied to solve a diverse range of problems in the areas of biomedical, biochemical and bioinformatics problems. By utilizing powerful computing resources and massive amounts of data, methods based on artificial intelligence can significantly improve the ...read more
Emerging trends in diseases mechanisms, noble drug targets and therapeutic strategies: focus on immunological and inflammatory disorders
Recently infectious and inflammatory diseases have been a key concern worldwide due to tremendous morbidity and mortality world Wide. Recent, nCOVID-9 pandemic is a good example for the emerging infectious disease outbreak. The world is facing many emerging and re-emerging diseases out breaks at present however, there is huge lack ...read more
Exploring Spectral Graph Theory in Combinatorial Chemistry
Scope of the Thematic Issue: Combinatorial chemistry involves the synthesis and analysis of a large number of diverse compounds simultaneously. Traditional methods rely on brute force experimentation, which can be time-consuming and resource-intensive. Spectral Graph Theory, a branch of mathematics dealing with the properties of graphs in relation to the ...read more
Integrating Network Pharmacology and Traditional Medicine: A New Perspective in Drug Mechanism Research
Network pharmacology is a network construction and network topology analysis strategy that combines pharmacology and pharmacodynamics. In recent years, network pharmacology has emerged as a powerful tool that can be integrated with pharmacology. Natural products commonly function in multicomponent, multitarget, and multipathway systems. Some examples encompass Ayurveda, traditional Chinese medicines ...read more
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers