Biomimetic design of amphiphilic polycations and surface grafting onto polycarbonate urethane film as effective antibacterial agents with controlled hemocompatibility

Abstract

The synthetic polycations are ideal candidates as antimicrobial agents, because they resemble natural antimicrobial peptides, but to render hemocompatibility to these materials is a great challenge. Herein, we used 2‐(tert‐butyl‐aminoethyl) methacrylate (TBAEMA), to synthesize its homopolymer and pegylated random and diblock copolymers with polyethyleneglycol methacrylate (PEGMA, Mn = 360 Da) by single‐electron transfer–living radical polymerization (SET‐LRP). In the second step, the secondary amino groups in the precursor polymers were quaternized with iodomethane and bromohexane, to obtain three series of quaternized polymers. The antimicrobial properties of these quaternized polymers were evaluated against Escherichia coli (E. coli), by studying the minimum inhibitory concentrations (MICs) which ranged between 32 and 200 mg L−1 and showed higher values for the quaternized random than the diblock copolymers. In addition to, we have also demonstrated the grafting of these polycations onto polycarbonate urethane film surfaces, which showed good killing efficacy against E. coli. Furthermore, the hemolysis of these materials was investigated against human red blood cells, which indicated that except the quaternized homopolymers that showed highest hemolysis, all other amphiphilic polycations exhibited very low hemolytic activity. Therefore, our designed materials with controlled structures and functionality, synthesized from cheaply available resources could serve as useful agents in the field of biomedicines and implantable materials. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 3166–3176

Hydrophilic PCU scaffolds prepared by grafting PEGMA and immobilizing gelatin to enhance cell adhesion and proliferation

“…PEGMA was grafted onto the surface of PCU scaffold by SI-ATRP method as reported by us previously [42,47,48]. Firstly, the amination PCU scaffolds were immersed in n-hexane/triethylamine solution (100/1, v/v) in a 150 mL three-necked flask.…”

Antimicrobial surfaces grafted random copolymers with REDV peptide beneficial for endothelialization

“…63,70 First, PCU-films were treated with hexamethylene diisocyanate with DBTDL as the catalyst at 50 1C for 90 min. After immersing in water for 12 h, the amino group terminated PCU-films were prepared.…”

“…The commonly utilized antimicrobial agents include quaternary ammonium compounds, small molecular weight antibiotics, and plant-derived antimicrobial agents. 8,[63][64][65] One example is eugenol, which has been popular for its analgesic and anti-inflammatory properties, antimicrobial activity, antipyretic activity and antianaphylactic properties. 66,67 The acrylate derivative of eugenyl methacrylate (EgMA) can covalently link eugenol to macromolecular chains without decreasing its natural properties.…”

Synthesis of polyhydroxyurethanes from di(trimethylolpropane) and their application to quaternary ammonium chloride-functionalized films

“…Since silver species, especially silver nanoparticles, are classically known as effective antimicrobial agents, Ag-conjugated polymer materials, including polyurethanes, have been prepared. 27,28,[33][34][35][36][37][38][41][42][43][44][45][46][47][48][49] For cationic moieties, quaternary ammonium salts (QAS), 27,28,[33][34][35][36][37][38][41][42][43][44][45][46] quaternary phosphonium salts, 46 and protonated amine groups 47-49 effectively generate antimicrobial properties. Furthermore, the leaching of highly concentrated Ag ions is considered to cause cytotoxicity.…”

“…[21][22][23][24][25][26]39,40 The antimicrobial activity of Ag nanoparticles depends on the particle size; therefore, the control of their size and uniform spreading of them in matrices are required. Nowadays, a wide variety of cationic polymers such as polyacrylates, 22,40,45 polymethacrylate, [41][42][43]46,49 polycarbonates, [33][34][35][36][37][38] polypeptides, 47 and polyamines 48 are designed and characterized for their antimicrobial properties in many matrices including solution, lms and gels. 23,24 On the other hand, cationic polymers with amphiphilicity possibly show broad-spectrum antimicrobial properties through membrane disrupting mechanisms.…”