김다함 (서울대학교) | 한빛사논문 > 한빛사

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김다함Dahham Kim

서울대학교

Angew. Chem.-Int. Edit., Sep 25 2023 | https://doi.org/10.1002/anie.202310665 Ultrafluorogenic Monochromophore-Type BODIPY-Tetrazine Series for Dual-Color Bioorthogonal Imaging with a Single Probe.

Dahham Kim 1‡, Hayoung Son^1‡, Seung Bum Park^2*

¹Seoul National University College of Natural Sciences, Chemistry, KOREA, REPUBLIC OF.

²Seoul National University, Department of Chemistry College of Natural Science, 1 Gwanak-ro, Gwanak-gu, 08826, Seoul, KOREA, REPUBLIC OF.

^‡These authors contributed equally to this work.

^*CORRESPONDING AUTHOR : Seung Bum Park

Abstract

Various fluorogenic probes utilizing tetrazine (Tz) as a fluorescence quencher and bioorthogonal reaction partner have been extensively studied over the past few decades. Herein, we synthesized a series of boron-dipyrromethene (BODIPY)-Tz probes using monochromophoric design strategy for bioorthogonal cellular imaging. The BODIPY-Tz probes exhibited excellent bicyclo[6.1.0]nonyne (BCN)-selective fluorogenicity with three- to four-digit-fold enhancements in fluorescence over a wide range of emission wavelengths, including the far-red region. Furthermore, we demonstrated the applicability of BODIPY-Tz probes in bioorthogonal fluorescence imaging of cellular organelles without washing steps. We also elucidated the aromatized pyridazine moiety as the origin of BCN-selective fluorogenic behavior. Additionally, we discovered that the fluorescence of the trans-cyclooctene (TCO) adducts was quenched in aqueous media via photoinduced electron transfer (PeT) process. Interestingly, we observed a distinctive recovery of the initially quenched fluorescence of BODIPY-Tz-TCO upon exposure to hydrophobic media, accompanied by a significant bathochromic shift of its emission wavelength relative to that exhibited by the corresponding BODIPY-Tz-BCN. Leveraging this finding, for the first time, we achieved dual-color bioorthogonal cellular imaging with a single BODIPY-Tz probe.

논문정보

형식Research article
게재일2023년 09월 (BRIC 등록일 2023-10-06)
연구진국내 연구진
분야 생명과학 > 분자생물학

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