Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 46, Pages 14642-14647Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709120
Keywords
bulk aggregation; dansyl fluorophore; fluorescence sensors; progesterone; self-aggregation
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Funding
- KIST [2E26110/CAP-16-02-KIST]
- National Research Foundation - Ministry of Science, ICT & Future Planning [NRF-2016M3A9B6902060, NRF-2017M3A9D8029942]
- National Research Foundation of Korea (NRF) [2015H1D3A1036045]
- National Research Foundation of Korea [2015H1D3A1036045, 2016M3A9B6902060] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Steroids are polycyclic compounds that share tetracyclic ring as core scaffold, and selective detection of a steroid is challenging owing to their structural similarities. The discovery of chemosensors that recognize progesterone by alteration of self-aggregation state is described, and these show significant fluorescence turn-on. A self-aggregated 48-membered dansyl library was screened against a series of metabolites in aqueous buffer and discovered two compounds (PG-1, PG-2) exhibited exceptional selectivity for progesterone. Following studies of aggregation properties of probes using dynamic light scattering and transmission electron microscopy supports progesterone recognition lead to the generation of bulk aggregates that induce fluorescence enhancement. Though many fluorescence sensing mechanisms have been proposed, a sensing mode based on the bulk aggregate formation of fluorophore has never been reported, and this may open a new avenue of chemosensor design.
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