Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 28, Pages 9435-9438Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b04077
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Funding
- National Science Foundation [CHE-1301092, CHE-1429195]
- Utah Agricultural Experiment Station, USTAR [UTA-01178]
- Utah State University Office of Research and Graduate Studies (PDRF Fellowship)
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1429195] Funding Source: National Science Foundation
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Molecular structures capable of intracellular information processing that couple responses from biomarker signals to the release of drug molecules represent intelligent delivery systems. Herein we report a chemophotonically driven, sense-of-logic carbon monoxide-releasing molecule (SL-photoCORM). This extended flavonol motif operates via an AND logic gate by first sensing the cellular environment via detection of thiols and then releasing CO when triggered with visible light and O-2. Overall, this approach couples the detection of a cellular redox biomarker with the ability to release a small molecule gasotransmitter known to trigger pathways involved in pro- and anti-inflammatory effects in a dose dependent manner. Significantly, the fluorescence properties of the flavonol-based SL-photoCORM produce a series of chemophotonic input responses via two photo chromatic switches (blue-to-green and green-to-colorless), leading to trackability and spatiotemporal control of CO release. Examination of the O-2 requirements of the CO release step revealed that the SL-photoCORM is suitable for use under conditions of variable cellular levels of O-2. These combined properties within a single-molecular framework advance the field of CO-releasing molecules by providing feedback on the diversity and complexity of the cellular environment prior to CO release.
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