title: Immobilization of antimicrobial peptide IG-25 onto fluoropolymers via fluorous interactions and click chemistry.
abstract: We report a practical method for biofunctionalization of fluoropolymers based on noncovalent, fluorous interactions and click chemistry that allows incorporation of biomolecules under physiological solutions. We demonstrate the method by immobilization of an antimicrobial peptide (AMP) on fluorous thin films and fluorosilicone contact lens. The fluorous surfaces were dip-coated with fluorous-tagged oligo(ethylene) chain terminated with a reactive group, such as an alkynyl group. This simple step generates a "clickable" surface. The noncovalent fluorous interaction was strong enough to allow subsequent covalent attachment of IG-25, a truncated version of the most extensively studied human AMP LL-37. The attachment was through copper-catalyzed click reaction between the alkynyl group on the surface and the azido-OEG tag at the N-terminus of IG-25. In comparison to surfaces presenting IG-25 randomly bound via carbodiimide chemistry, the surfaces presenting IG-25 tethering to the surface at the N-terminus via click chemistry displayed higher antibacterial activities against an ocular pathogen Pseudomonas aeruginosa (strain PA-O1).
authors.affiliation: Department of Chemistry and ‡College of Optometry, University of Houston , Houston, Texas 77204, United States.
authors.forename: Catherine M
authors.initials: CM
authors.lastname: Santos
authors.forename: Amit
authors.initials: A
authors.lastname: Kumar
authors.forename: Satya S
authors.initials: SS
authors.lastname: Kolar
authors.forename: Rafael
authors.initials: R
authors.lastname: Contreras-Caceres
authors.forename: Alison
authors.initials: A
authors.lastname: McDermott
authors.forename: Chengzhi
authors.initials: C
authors.lastname: Cai
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism; D023181:Antimicrobial Cationic Peptides / Q000737:chemistry* / Q000378:metabolism; D057930:Click Chemistry; D003261:Contact Lenses / Q000382:microbiology; D019793:Fluorescein / Q000737:chemistry; D006801:Humans; D055767:Immobilized Proteins / Q000737:chemistry* / Q000378:metabolism; D011108:Polymers / Q000737:chemistry*; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012828:Silicones / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D023181:Antimicrobial Cationic Peptides; C556980:I-G-K-E-F-K-R-I-V-Q-R-I-K-D-F-L-R-N-L-V-P-R-T-E-S; D055767:Immobilized Proteins; D011108:Polymers; D012828:Silicones; D019793:Fluorescein