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Design and Synthesis of a Calcium-Sensitive Photocage.

ABSTRACT: Photolabile protecting groups (or "photocages") enable precise spatiotemporal control of chemical functionality and facilitate advanced biological experiments. Extant photocages exhibit a simple input-output relationship, however, where application of light elicits a photochemical reaction irrespective of the environment. Herein, we refine and extend the concept of photolabile groups, synthesizing the first Ca(2+) -sensitive photocage. This system functions as a chemical coincidence detector, releasing small molecules only in the presence of both light and elevated [Ca(2+) ]. Caging a fluorophore with this ion-sensitive moiety yields an "ion integrator" that permanently marks cells undergoing high Ca(2+) flux during an illumination-defined time period. Our general design concept demonstrates a new class of light-sensitive material for cellular imaging, sensing, and targeted molecular delivery.

SUBMITTER: Heckman LM

PROVIDER: S-EPMC6680284 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Design and Synthesis of a Calcium-Sensitive Photocage.

Heckman Laurel M LM Grimm Jonathan B JB Schreiter Eric R ER Kim Charles C Verdecia Mark A MA Shields Brenda C BC Lavis Luke D LD

Angewandte Chemie (International ed. in English) 20160524 29

Photolabile protecting groups (or "photocages") enable precise spatiotemporal control of chemical functionality and facilitate advanced biological experiments. Extant photocages exhibit a simple input-output relationship, however, where application of light elicits a photochemical reaction irrespective of the environment. Herein, we refine and extend the concept of photolabile groups, synthesizing the first Ca(2+) -sensitive photocage. This system functions as a chemical coincidence detector, re ...[more]

PMID: 27218487

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