Cytomimetic Biomaterials. 1. In-Situ Polymerization of Phospholipids on an Alkylated Surface

Abstract

A stabilized, phosphatidylcholine-containing polymeric surface was produced by in-situ polymerization of a self-assembled lipid monolayer on an alkylated substrate. The phospholipid monomer 1-palmitoyl-2-[12-(acryloyloxy)dodecanoyl]-sn-glycero-3-phosphorylcholine was synthesized, prepared as unilamellar vesicles, and fused onto alkylated glass. Free-radical polymerization was carried out in aqueous solution at 70 °C and characterized using either the water-soluble initiator 2,2‘-azobis(2-methylpropionamidine) dihydrochloride (AAPD) or an oil-soluble initiator 2,2‘-azobis(isobutyronitrile) (AIBN). Under optimized conditions, the supported monolayer displayed advancing and receding water contact angles of 64 and 44°, respectively. Angle-dependent ESCA results confirmed the presence of phosphorus and nitrogen and were consistent with theoretical predictions for close-packed monolayer formation with near-normal alignment of lipid chains. In the absence of network formation, polymeric films demonstrated acceptable stability under static conditions in water and air, as well as in the presence of a high shear flow environment. Blood compatibility was assessed in a baboon arteriovenous shunt model, which revealed miminal platelet deposition over a 2 h observation period.

Surface modification of titanium, titanium alloys, and related materials for biomedical applications

“…Surface modification typically follows two approaches. The first one is to generate hydroxylterminated monolayers [195,198,199] and the second one is to utilize the chemical or physical adsorption of phospholipids or phospholipid derivatives on alkylsilane monolayers [196,197,[200][201][202][203]. Protein adsorption and cell adhesion are reduced on the phosphorylcholine-assembled surfaces.…”

Atomized Spray Plasma Deposition of Structurally Well-Defined Bioactive Coatings

“…4 For instance, immobilized phospholipid surfaces 5 are used for biosensing, 6,7 biomimesis, 8,9 bioseparation, 10 vesicle binding, 11,12 biocompatibility, 13,14 and enzyme immobilization. 15 Phospholipids are a type of amphiphilic lipid comprising a hydrophilic phosphate head group and a straight alkyl chain hydrophobic tail group.…”

Membrane–mimetic films containing thrombomodulin and heparin inhibit tissue factor-induced thrombin generation in a flow model

“…Poly(L-lysine) (PLL, MW4300 kDa) and all buffer salts are obtained from Sigma. Synthesis of monoacrylate-PC (AcPC,1-palmitoyl-2-[12-(acryloyloxy)dodecanoyl]-sn-glycero-3-phosphocholine), monoacrylate-PE (1-palmitoyl-2-(12-(acryloyloxy)dodecanoyl)-sn-glycero-3-phosphoethanolamine) and its biotin derivative (biotin-AcPE, mono-acrylPEbiotin) have been described previously [36,37]. Likewise, the synthesis of a terpolymer that consists (3-acryloyl-3-oxapropyl-3-(N,N-dioctadecyl-carbamoyl)-propionate)) 6 :(2-hydroxyethyl acrylate) 3 :sodium styrene sulfonate 1 (AOD 6 :HEA 3 :SS 1 ) has been described elsewhere [38].…”