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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.

SUBMITTER: Tautges B

PROVIDER: S-EPMC4649948 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Preparation of a conjugation-ready thiol responsive molecular switch.

Tautges Brandon B Or Victor V Garcia Joel J Shaw Jared T JT Louie Angelique Y AY

Tetrahedron letters 20151101 47

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 cys ...[more]

PMID: 26594066

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