title: Preparation of a conjugation-ready thiol responsive molecular switch.
abstract: In this work we synthesize molecular switches that are responsive to cysteine, homocysteine, and glutathione; three redox systems that make up the majority of the body's antioxidant defenses. Synthesized spiropyran isomers with conjugation-ready linkages showed good selectivity of response to these major antioxidant thiols over nucleophilic amino acids; however the position of the linking group can affect selectivity and reversibility of the switching response. An isomer with selectivity for cysteine against GSH and Hcy was identified.
authors.affiliation: Department of Chemistry, University of California at Davis, One Shields Ave, Davis, California 95616, United States.
authors.forename: Brandon
authors.initials: B
authors.lastname: Tautges
authors.affiliation: Department of Chemistry, University of California at Davis, One Shields Ave, Davis, California 95616, United States.
authors.forename: Victor
authors.initials: V
authors.lastname: Or
authors.affiliation: Department of Biomedical Engineering, University of California at Davis, One Shields Ave, Davis, California 95616, United States.
authors.forename: Joel
authors.initials: J
authors.lastname: Garcia
authors.affiliation: Department of Chemistry, University of California at Davis, One Shields Ave, Davis, California 95616, United States.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw
authors.affiliation: Department of Biomedical Engineering, University of California at Davis, One Shields Ave, Davis, California 95616, United States.
authors.forename: Angelique Y
authors.initials: AY
authors.lastname: Louie
keywords: Colorimetric Sensor; Spiropyran; Thiol