title: Controlling biological activity with light: diarylethene-containing cyclic peptidomimetics.
abstract: Photobiological processes in nature are usually triggered by nonpeptidic chromophores or by modified side chains. A system is presented in which the polypeptide backbone itself can be conformationally switched by light. An amino acid analogue was designed and synthesized based on a reversibly photoisomerizable diarylethene scaffold. This analogue was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S at several sites. The biological activity of the resulting peptidomimetics could then be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.
authors.affiliation: Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry and CFN, Fritz-Haber-Weg 6, 76131 Karlsruhe (Germany).
authors.forename: Oleg
authors.initials: O
authors.lastname: Babii
authors.forename: Sergii
authors.initials: S
authors.lastname: Afonin
authors.forename: Marina
authors.initials: M
authors.lastname: Berditsch
authors.forename: Sabine
authors.initials: S
authors.lastname: Reiβer
authors.forename: Pavel K
authors.initials: PK
authors.lastname: Mykhailiuk
authors.forename: Vladimir S
authors.initials: VS
authors.lastname: Kubyshkin
authors.forename: Thomas
authors.initials: T
authors.lastname: Steinbrecher
authors.forename: Anne S
authors.initials: AS
authors.lastname: Ulrich
authors.forename: Igor V
authors.initials: IV
authors.lastname: Komarov
mesh_terms: D005030:Ethylenes / Q000737:chemistry*; D008027:Light; D008958:Models, Molecular; D008968:Molecular Conformation; D010456:Peptides, Cyclic / Q000737:chemistry*; D057786:Peptidomimetics / Q000737:chemistry*; D010777:Photochemistry; D013329:Structure-Activity Relationship
chemical_list: D005030:Ethylenes; D010456:Peptides, Cyclic; D057786:Peptidomimetics
keywords: antimicrobial agents; diarylethenes; gramicidin S; peptidomimetics; photochemistry