Synthesis and antibacterial activity of nisin-containing block copolymers.
Nisin, an antibacterial peptide proven to be an effective inhibitor of Gram-positive bacteria, was incorporated into novel block copolymer constructs and tested for retained antibacterial activity. Covalent coupling was achieved by chemical modification of the N-terminal isoleucine to introduce a thiol group. Thiolated-nisin derivatives were then linked to poly[ethylene oxide]-poly[propylene oxide]-poly[ethylene oxide] (PEO-PPO-PEO) triblocks that had been end-activated such that terminal hydroxyl groups of the PEO chains were replaced with pyridyl disulfide moieties. The nisin-containing block copolymers were separated from free nisin by dialysis and showed antimicrobial activity against the Gram-positive indicator strain Pediococcus pentosaceus. The contribution to antimicrobial activity from nisin that was covalently linked was not distinguished from the contribution of nisin that had associated with the PEO-PPO-PEO triblocks through noncovalent interactions. However, nisin that was covalently linked showed activity upon reduction of the disulfide bond and release from the end-activated PEO.
Department of Chemical Engineering, Oregon State University, Corvallis, Oregon 97331, USA.
Pranav R
PR
Joshi
Joseph
J
McGuire
Jennifer A
JA
Neff
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001672:Biocompatible Materials; D008422:Materials Testing; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009561:Nisin / Q000737:chemistry / Q000494:pharmacology; D010376:Pediococcus / Q000187:drug effects; D011092:Polyethylene Glycols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011409:Propylene Glycols / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013438:Sulfhydryl Compounds / Q000737:chemistry
D000900:Anti-Bacterial Agents; D001672:Biocompatible Materials; C116176:PEO-PPO-PEO; D011108:Polymers; D011409:Propylene Glycols; D013438:Sulfhydryl Compounds; D009561:Nisin; D011092:Polyethylene Glycols