title: Ciprofloxacin-Photoswitch Conjugates: A Facile Strategy for Photopharmacology.
abstract: Photopharmacology aims to locally treat diseases and study biological processes with photoresponsive drugs. Herein, easy access to photoswitchable drugs is crucial, which is supported by simple and robust drug modifications. We investigated the possibility of creating drugs that can undergo remote activation and deactivation with light, by conjugating molecular photoswitches to the exterior of an existing drug in a single chemical step. This facile strategy allows the convenient introduction of various photochromic systems into a drug molecule, rendering it photoresponsive. To demonstrate the feasibility of this approach, two photoswitch-modified ciprofloxacin antibiotics were synthesized. Remarkably, for one of them a 50-fold increase in activity compared to the original ciprofloxacin was observed. Their antimicrobial activity could be spatiotemporally controlled with light, which was exemplified by bacterial patterning studies.
authors.affiliation: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors.forename: Willem A
authors.initials: WA
authors.lastname: Velema
authors.affiliation: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors.forename: Mickel J
authors.initials: MJ
authors.lastname: Hansen
authors.affiliation: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors.forename: Michael M
authors.initials: MM
authors.lastname: Lerch
authors.affiliation: Molecular Microbiology, Groningen Biomolecular Sciences and Biotechnology Institute , Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
authors.forename: Arnold J M
authors.initials: AJ
authors.lastname: Driessen
authors.affiliation: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 AG, Groningen, The Netherlands.|Department of Radiology, University of Groningen, University Medical Centre Groningen , 9713 GZ, Groningen, The Netherlands.
authors.forename: Wiktor
authors.initials: W
authors.lastname: Szymanski
authors.affiliation: Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
authors.forename: Ben L
authors.initials: BL
authors.lastname: Feringa
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D002939:Ciprofloxacin / Q000737:chemistry* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D004927:Escherichia coli Infections / Q000188:drug therapy; D006801:Humans; D008027:Light; D010777:Photochemistry / Q000379:methods*
chemical_list: D000900:Anti-Bacterial Agents; D002939:Ciprofloxacin