Oxidation of Tertiary Amine-Derivatized Surfaces To Control Protein Adhesion

Abstract

Selective oxidation of ω-tertiary amine self-assembled thiol monolayers to tertiary amine N-oxides is shown to transform the adhesion of model proteins lysozyme and fibrinogen upon them. Efficient preparation of both secondary and tertiary linker amides as judged by X-ray photoelectron spectroscopy (XPS) and water droplet contact angle was achieved with an improved amide bond formation on gold quartz crystal microbalance (QCM) sensors using 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyl hexafluorophosphate methanaminium uronium (HATU). Oxidation with hydrogen peroxide was similarly assessed, and adhesion of lysozyme and fibrinogen from phosphate buffered saline was then assayed by QCM and imaged by AFM. Tertiary amine-functionalized sensors adsorbed multilayers of aggregated lysozyme, whereas tertiary amine N-oxides and triethylene glycol-terminated monolayers are consistent with small protein aggregates. The surface containing a dimethylamine N-oxide headgroup and ethyl secondary amide linker showed the largest difference in adsorption of both proteins. Oxidation of tertiary amine decorated surfaces therefore holds the potential for selective deposition of proteins and cells through masking and other patterning techniques.

Zwitterionization of Tertiary Amines in Nanoporous Block Copolymers: toward Fouling-Resistant Ultrafiltration Membranes

“…After soaking the film in the H 2 O 2 solution at 60 °C for 0.5 h, a new peak located at 403 eV appeared, which should be attributed to N + in tertiary amine N-oxides. 38 This evidences the formation of zwitterions and the efficiency of this in situ oxidation strategy, which are in good agreement with other characterization results discussed above. The conversion of tertiary amine Noxides can be calculated using eq 8 conditions and then investigated their separation perform-Note that the preparation of the PTMAO-zwitterionized membranes can be significantly accelerated by finishing the swelling process within 1 min through a microwave-boosted selective swelling strategy 39 and shortening the oxidation to <2 h, which can also achieve a conversion of 80%.…”

Efficient anoxic pollutant removal with oxygen functionalized graphitic carbon nitride under visible light

“…This peak could be attributed to the amine oxide groups (C 3 -N + -O À ) formed by oxidation of tertiary amines with H 2 O 2 . 26 The formation of amine oxide groups on O-g-C 3 N 4 was further conrmed by ESR spectra analysis. Fig.…”

Data-Driven Prediction of Protein Adsorption on Self-Assembled Monolayers toward Material Screening and Design

“…Three data sets were prepared from the gathered gold-based SAMs data from several publications. − All values in the database are shown in the Supporting Information.…”