Glycosaminoglycan‐Induced Emissive J‐Aggregate Formation in a meso‐Ester BODIPY Dye. Issue 14 (5th June 2020)

• Record Type: Journal Article
• Authors: Kim, Dami; Lee, Uisung; Bouffard, Jean; Kim, Youngmi
• Is Part Of: Advanced optical materials. Volume 8:Issue 14(2020)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-06-05
• Subjects: aggregation‐induced emission (AIE) -- BODIPY -- fluorescent probes -- heparin -- J‐aggregates; Optical materials -- Periodicals; Photonics -- Periodicals; 620.11295
• DOI: 10.1002/adom.201902161
• Languages: English
• ISSNs: 2195-1071

Abstract

Abstract: The analyte‐directed formation of emissive J‐aggregates of a meso ‐ester BODIPY dye is explored in the design of fluorescence "light‐up" probes. The heparin‐specific pyridinium‐functionalized meso ‐ester BODIPY dye C10‐Py + self‐assembles in aqueous buffer into spherical aggregated nanostructures with spectroscopic features indistinguishable from the monomeric dye (signal off). In the presence of heparin, the aggregated assemblies rearrange and associate with heparin through charge‐pairing interactions, triggering the spontaneous formation of emissive J‐type aggregates (signal on). The heparin‐induced J‐aggregate formation of C10‐Py + provides an excellent "turn‐on" signal with large spectral shifts. The response is highly selective for heparin over other closely related glycosaminoglycan (GAG) analogues, sensitive, fast, and operationally simple. Assays for heparin in human serum, and for the adulterant OSCS in heparin are demonstrated, confirming the reliability and robustness of the J‐aggregation approach using meso ‐ester BODIPY dyes in the design of aggregation‐induced emission (AIE)‐based fluorogenic probes. Abstract : The pyridinium‐functionalized meso ‐ester BODIPY dye C10‐Py + reliably and selectively forms emissive J‐aggregates upon complexation with heparin. The resulting "turn‐on" fluorescence response is used to develop assays for the quantitation of heparin in water or blood serum samples, and for the detection of adulterated samples of pharmaceutical heparin.