Controlling Biological Activity with Light: Diarylethene-Containing Cyclic Peptidomimetics

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 photoi...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2014-03, Vol.53 (13), p.3392-3395
Main Authors: Babii, Oleg, Afonin, Sergii, Berditsch, Marina, Reiβer, Sabine, Mykhailiuk, Pavel K., Kubyshkin, Vladimir S., Steinbrecher, Thomas, Ulrich, Anne S., Komarov, Igor V.
Format: Article
Language:English
Subjects:
Amino acids
Analogue
Antiinfectives and antibacterials
antimicrobial agents
Backbone
Biological
Biological activity
diarylethenes
Ethylenes - chemistry
gramicidin S
Light
Models, Molecular
Molecular Conformation
Peptides, Cyclic - chemistry
peptidomimetics
Peptidomimetics - chemistry
Photochemistry
Scaffolds
Structure-Activity Relationship
Temporal logic
Ultraviolet
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Summary: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. Making light work: An amino acid analogue based on a reversibly photoisomerizable diarylethene scaffold was incorporated into the cyclic backbone of the antimicrobial peptide gramicidin S. The biological activity of the resulting peptidomimetics could be effectively controlled by ultraviolet/visible light within strictly defined spatial and temporal limits.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201310019