Thiol surface functionalization via continuous phase plasma polymerization of allyl mercaptan, with subsequent maleimide-linked conjugation of collagen

Journal article


Stynes, Gil D., Gengenbach, Thomas R., Kiroff, George K., Morrison, Wayne A. and Kirkland, Mark A.. (2017). Thiol surface functionalization via continuous phase plasma polymerization of allyl mercaptan, with subsequent maleimide-linked conjugation of collagen. Journal of Biomedical Materials Research Part A. 105(7), pp. 1940-1948. https://doi.org/10.1002/jbm.a.36064
AuthorsStynes, Gil D., Gengenbach, Thomas R., Kiroff, George K., Morrison, Wayne A. and Kirkland, Mark A.
Abstract

Thiol groups can undergo a large variety of chemical reactions and are used in solution phase to conjugate many bioactive molecules. Previous research on solid substrates with continuous phase glow discharge polymerization of thiol-containing monomers may have been compromised by oxidation. Thiol surface functionalization via glow discharge polymerization has been reported as requiring pulsing. Herein, continuous phase glow discharge polymerization of allyl mercaptan (2-propene-1-thiol) was used to generate significant densities of thiol groups on a mixed macrodiol polyurethane and tantalum. Three general classes of chemistry are used to conjugate proteins to thiol groups, with maleimide linkers being used most commonly. Here the pH specificity of maleimide reactions was used effectively to conjugate surface-bound thiol groups to amine groups in collagen. XPS demonstrated surface-bound thiol groups without evidence of oxidation, along with the subsequent presence of maleimide and collagen. Glow discharge reactor parameters were optimized by testing the resistance of bound collagen to degradation by 8 M urea. The nature of the chemical bonding of collagen to surface thiol groups was effectively assessed by colorimetric assay (ELISA) of residual collagen after incubation in 8 M urea over 8 days and after incubation with keratinocytes over 15 days. The facile creation of useable solid-supported thiol groups via continuous phase glow discharge polymerization of allyl mercaptan opens a route for attaching a vast array of bioactive molecules.

Keywordsplasma chemistry; thiol; surface analysis; biological activity; protein engineering
Year2017
JournalJournal of Biomedical Materials Research Part A
Journal citation105 (7), pp. 1940-1948
PublisherJohn Wiley & Sons, Inc.
ISSN1549-3296
Digital Object Identifier (DOI)https://doi.org/10.1002/jbm.a.36064
Scopus EID2-s2.0-85019688266
Research or scholarlyResearch
Page range1940-1948
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All rights reserved
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Controlled
Output statusPublished
Publication dates
Online10 Mar 2017
Publication process dates
Accepted07 Mar 2017
Deposited14 Jun 2021
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