Live bio-imaging with fully bio-compatible organic fluorophores

Yang, Inho; Lee, Jong Woo; Hwang, Sun‐Jin; Lee, Jung Eun; Lim, Eunhak; Lee, June; Hwang, Doyk; Kim, Clara H.; Keum, Young‐Sam; Kim, Seong Keun

doi:10.1016/j.jphotobiol.2016.11.009

Cited by 11 publications

(5 citation statements)

References 34 publications

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“…Figure B explores the fluorescence changes in the experiment. It can be seen that B-AIEgens shows a maximum emission wavelength of 617 nm, allowing its fluorescence profile to show a large Stokes shift (137 nm), which facilitates fluorescence imaging of plant tissues . After optimization of the substance ratio and reaction time, changes in fluorescence during the experimental correlation were explored (Figures S6 and S7).…”

Section: Resultsmentioning

confidence: 99%

Biocompatible Abscisic Acid-Sensing Supramolecular Hybridization Probe for Spatiotemporal Fluorescence Imaging in Plant Tissues

Yin

Jiang

et al. 2022

Anal. Chem.

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Achieving detection of the phytohormone abscisic acid (ABA) is of critical importance for understanding plant growth and development. We report a hybrid supramolecular fluorescent probe that uses bovine serum albumin (BSA) as a host. Aggregation-induced emission of fluorescent chromophores (AIEgens) enables luminescence in the presence of BSA. ABA and its aptamer act as a switch to trigger this fluorescent system, the strategy that exhibits high sensitivity to abscisic acid with a detection limit of 0.098 nM. The probe test strip also enables visualization of ABA content from plants by colorimetric observation with the naked eye. In particular, the high biocompatibility and small molecular size of the prepared fluorescent probe allow for effective monitoring of ABA in plant tissues by fluorescence imaging. This strategy provides a new perspective to achieve the detection of endogenous and exogenous ABA in plants and has important implications for plant biology research.

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Section: Resultsmentioning

confidence: 99%

Biocompatible Abscisic Acid-Sensing Supramolecular Hybridization Probe for Spatiotemporal Fluorescence Imaging in Plant Tissues

Yin

Jiang

et al. 2022

Anal. Chem.

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“…a) . In addition to simple and straightforward synthesis, as it only involves light irradiation and purification, resveratrone possesses several useful properties as a fluorophore, including high quantum yield, large Stokes shift and two-photon absorption coefficient, and very high biocompatibility. , Despite its high potential application for biological discipline, the study of its photophysical process is still lacking, and the ground for its large Stokes shift and quantum yield remains elusive. This lack hinders further utilization of the compound.…”

Section: Introductionmentioning

confidence: 99%

Alcoholic Solvent-Mediated Excited-State Proton Transfer Dynamics of a Novel Dihydroxynaphthalene Dye

Han,

Lim,

Kang

et al. 2023

J. Phys. Chem. A

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The excited-state proton transfer (ESPT) reaction is an important primary photochemical process because it is closely related to photophysical properties. Although ESPT research in aqueous solutions is predominant, alcoholic solvent-mediated ESPT studies are also significant in terms of photoacid−based reactions. Especially, the research for dihydroxynaphthalenes (DHNs) has been largely neglected due to the challenging data interpretation of two hydroxyl groups. A novel fluorescent dye, resveratrone, synthesized by light irradiation of resveratrol, which is famous for its antioxidant properties, can be regarded as a type of DHN, and it has distinctive optical properties, including high quantum yield, a large two-photon absorption coefficient, a large Stokes shift, and very high biocompatibility. In this study, we investigate the overall kinetics of the optical properties of resveratrone and find evidence for alcoholic solvent-mediated ESPT involvement in the radiative properties of resveratrone with a large Stokes shift. Our investigation provides an opportunity to revisit the overlooked photophysical properties of intriguing photoacid behavior and the large Stokes shift of the dihydroxynaphthalene dye.

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“…In 2012, Kim and co‐workers have reported that resveratrol ( 1 ) reacts to resveratrone ( 2 ) under UV irradiation as shown in Scheme 1A [4] . Resveratrone ( 2 ) is a highly fluorescent compound that can undergo two‐photon absorption, making it interesting for bio‐labelling applications [4a, 5] . More recently, the photo‐switchability between 1 and 2 has been utilized by Voskuhl, Giese and co‐workers for the preparation of light‐responsive liquid crystals [6] .…”

Section: Introductionmentioning

confidence: 99%

“…The epoxide olefination method em-ployed was reported by us in 2019, [9] utilizing epoxides such as 4, or even their more highly substituted congeners. Epoxides of type 4 can be lithiated in the presence of boronic esters, [7] thus forming ate-complexes (5), which can undergo 1,2-metallate rearrangements to β-alkoxy boronates (6; Scheme 2). [9] Stereospecific syn-elimination delivers alkenes of type 7 as well as their tri-and tetrasubstituted congeners upon iterative application.…”

Section: Introductionmentioning

confidence: 99%

Total Synthesis of Resveratrone andiso‐Resveratrone

et al. 2022

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The first total synthesis of resveratrone and iso‐resveratrone based on an epoxide olefination approach is described. The pivotal reaction proceeds by insertion of the lithiated epoxide into a boronic ester and subsequent syn‐elimination. Resveratrone has been described to have remarkable photophysical properties, including two‐photon absorption. Therefore, an azide derivative has been prepared to allow for use as a biological label.

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Live bio-imaging with fully bio-compatible organic fluorophores

Cited by 11 publications

References 34 publications

Biocompatible Abscisic Acid-Sensing Supramolecular Hybridization Probe for Spatiotemporal Fluorescence Imaging in Plant Tissues

Biocompatible Abscisic Acid-Sensing Supramolecular Hybridization Probe for Spatiotemporal Fluorescence Imaging in Plant Tissues

Alcoholic Solvent-Mediated Excited-State Proton Transfer Dynamics of a Novel Dihydroxynaphthalene Dye

Total Synthesis of Resveratrone andiso‐Resveratrone

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