Glycosaminoglycan-Induced Emissive J-Aggregate Formation in a meso-Ester BODIPY Dye

Dami Kim, Uisung Lee, Jean Bouffard, Youngmi Kim

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20 Scopus citations

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.

Original languageEnglish
Article number1902161
JournalAdvanced Optical Materials
Volume8
Issue number14
DOIs
StatePublished - 1 Jul 2020

Bibliographical note

Funding Information:
This research was supported by National Research Foundation of Korea (NRF) grants funded by the Korean government (MSIP) (NRF‐2018R1D1A1B07044894 and NRF‐2015R1A5A1008958) and a grant from Kyung Hee University in 2019 (KHU‐20191208). The authors thank Dr. Weon‐Sik Chae of the KBSI Daegu Center for fluorescence lifetime measurements.

Funding Information:
This research was supported by National Research Foundation of Korea (NRF) grants funded by the Korean government (MSIP) (NRF-2018R1D1A1B07044894 and NRF-2015R1A5A1008958) and a grant from Kyung Hee University in 2019 (KHU-20191208). The authors thank Dr. Weon-Sik Chae of the KBSI Daegu Center for fluorescence lifetime measurements.

Publisher Copyright:
© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • BODIPY
  • J-aggregates
  • aggregation-induced emission (AIE)
  • fluorescent probes
  • heparin

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