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

Langmuir : the ACS Journal of Surfaces and Colloids
Hanqi WangJingping Qu

Abstract

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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Citations

Jun 17, 2020·Biomedical Materials·Mariah SarwatAurelien Forget
Apr 2, 2020·Materials Science & Engineering. C, Materials for Biological Applications·Luciano D SappiaOmar Azzaroni
May 11, 2021·Journal of Controlled Release : Official Journal of the Controlled Release Society·Chi Ming Laurence LauYing Chau
Nov 23, 2019·Langmuir : the ACS Journal of Surfaces and Colloids·Mingyang LiQing Wang
May 25, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·Fang ChengJingping Qu
Jul 25, 2018·Chemical Reviews·Christopher D SpicerMolly M Stevens
Jan 31, 2020·ACS Applied Materials & Interfaces·Julieta I PaezAránzazu Del Campo

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