Bioinspired Blood Compatible Surface Having Combined Fibrinolytic and Vascular Endothelium‐Like Properties via a Sequential Coimmobilization Strategy

Abstract

Developing surfaces with antithrombotic properties is of great interest for the applications of blood-contacting biomaterials and medical devices. It is promising to coimmobilize two or more biomolecules with different and complementary functions to improve blood compatibility. However, the general one-pot strategy usually adopted by previous studies suffers the problems of inevitable competition between diverse biomolecules and uncontrollability of the relative quantities of the immobilized biomolecules. To solve these problems, a new sequential coimmobilization strategy is proposed and applied to fabricate a blood compatible surface. Polyurethane surface is modifi ed with a copolymer, poly(2-hydroxyethyl methacrylate-co-1-adamantan-1-ylmethyl methacrylate), which serves as a linker-spacer for sequential attachment of two functional molecules, a hexapeptide containing REDV (Arg-Glu-Asp-Val) sequence, and a modifi ed cyclodextrin bearing 7 lysine ligands, through covalent bonding and host-guest interaction, respectively. The resulting surface combines the antithrombogenic properties of the vascular endothelium and the clot lysing properties of the fi brinolytic system. Importantly, neither of the two functions of REDV peptide and lysine is compromised by the presence of the other, suggesting the enhanced blood compatibility. These results suggest a new strategy to engineer multifunctional surfaces by coimmobilization of bioactive molecules having unique functionalities.

A multifunctional surface for blood contact with fibrinolytic activity, ability to promote endothelial cell adhesion and inhibit smooth muscle cell adhesion

“…Tecothane (TT-1095A) polyurethane (PU) was from Thermedics (Wilmington, MA, USA) and was purified by Soxhlet extraction with methanol, toluene and methanol each for 48 h. 6-amino-2-(2-methacylamido)-hexanoic acid (LysMA), 17 6-(4sulfonylmethyl-1H-[1,2,3]triazol-1-yl)-6-deoxy-β-cyclodextrin (CD-S) 18 , AdaMA 19 and fluorescein isothiocyanate modified βcyclodextrin (CD-FITC) 20 were prepared as described previously. 2, 2'-Azoisobutyronitrile (AIBN) from Tokyo Chemical Industry Company was recrystallized from methanol solution and dried under vacuum.…”

Responsive and Synergistic Antibacterial Coatings: Fighting against Bacteria in a Smart and Effective Way

“…To this end, we designed a multivalent biocidal compound named CD‐QAS, which was synthesized by conjugation of seven QAS groups to the primary hydroxyl groups on the narrow rim of β‐cyclodextrin (β‐CD) via click chemistry . As shown in Figure a, the unique chemical structure of CD‐QAS possesses several advantages to make it suitable for the fabrication of regenerable smart antibacterial coatings: i) seven QAS groups on the narrow rim increase the local density of biocidal groups and thus enhance the antibacterial activity due to multivalent effect; ii) the hydrophobic cavity is suitable for the inclusion of guest molecules such as adamantine (Ada) and azobenzene (Azo) via supramolecular host–guest interaction; and iii) the secondary hydroxyl groups on the wide rim exhibit diol structure that can bind to phenylboronic acid (PBA) groups via sugar/pH‐responsive dynamic boronate ester bonds. [103c] It is demonstrated that the host–guest interaction between Azo and β‐CD was light‐responsive due to light‐triggered conformational transition between trans ‐Azo and cis ‐Azo; the trans ‐Azo can form stable complex with β‐CD while the cis ‐Azo cannot due to the size difference .…”

Surfaces having dual affinity for plasminogen and tissue plasminogen activator: in situ plasmin generation and clot lysis

“…25 The 1 H NMR spectrum confirming the expected structure is shown in ESI, † 25 The 1 H NMR spectrum confirming the expected structure is shown in ESI, † …”