Reactivity and kinetics of vinyl sulfone-functionalized self-assembled monolayers for bioactive ligand immobilization

A new vinyl sulfone (VS) disulfide, 1,2-bis(11-(vinyl sulfonyl)undecyl)disulfane, was synthesized to enable the preparation of VS-presenting self-assembled monolayers (VS SAMs) on Au substrates. The VS SAMs were used as a model system to assess the reaction kinetics of bioactive ligands, i.e., gluta...

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Veröffentlicht in:Langmuir : the ACS journal of surfaces and colloids. - 1992. - 31(2015), 11 vom: 24. März, Seite 3413-21
1. Verfasser: Wang, Hanqi (VerfasserIn)
Weitere Verfasser: Cheng, Fang, Li, Mingyang, Peng, Wei, Qu, Jingping
Format: Online-Aufsatz
Sprache:English
Veröffentlicht: 2015
Zugriff auf das übergeordnete Werk:Langmuir : the ACS journal of surfaces and colloids
Schlagworte:Journal Article Research Support, Non-U.S. Gov't Sulfones divinyl sulfone 5PFN71LP8M Glutathione GAN16C9B8O
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520 |a A new vinyl sulfone (VS) disulfide, 1,2-bis(11-(vinyl sulfonyl)undecyl)disulfane, was synthesized to enable the preparation of VS-presenting self-assembled monolayers (VS SAMs) on Au substrates. The VS SAMs were used as a model system to assess the reaction kinetics of bioactive ligands, i.e., glutathione (GSH), N-(5-amino-1-carboxypentyl)iminodiacetic acid (ab-NTA), and mannose, toward the VS groups on the SAM surface. The VS SAMs and the ligand immobilization were characterized by X-ray photoelectron spectroscopy (XPS), contact angle goniometry, and protein-binding experiments using a quartz crystal microbalance (QCM). Kinetic studies showed that the surface VS groups undergo pseudo-first-order reactions with various ligands, with the observed rate constant being 0.057 min(-1) for GSH at pH 7.5, 0.011 min(-1) for ab-NTA at pH 8.5, and 0.009 min(-1) for mannose at pH 10.5. This work advanced our understanding of the reactivity of VS-bearing functional surfaces and further demonstrated the versatile potential of VS chemistry to prepare ligand-immobilized bioactive surfaces 
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700 1 |a Cheng, Fang  |e verfasserin  |4 aut 
700 1 |a Li, Mingyang  |e verfasserin  |4 aut 
700 1 |a Peng, Wei  |e verfasserin  |4 aut 
700 1 |a Qu, Jingping  |e verfasserin  |4 aut 
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