Fluorogenic, Two-Photon-Triggered Photoclick Chemistry in Live Mammalian Cells

Yu, Zhipeng; Ohulchanskyy, Tymish Y.; An, Peng; Prasad, Paras N.; Lin, Qing

doi:10.1021/ja407867a

“…To reduce light scattering and improve three dimensional localization of excitation, the two-photon excitation (2PE) of tetrazoles was demonstrated with the naphthalene-based derivatives [34]. By taking advantage of the known 2PE of naphthalene [35], various naphthalene-based tetrazole derivatives were synthesized and tested ( 57–59 ) (Fig.…”

Section: Photoinduced 13-dipolar Cycloaddition Reaction Between Tementioning

confidence: 99%

Photo-Triggered Click Chemistry for Biological Applications

Herner

¹

,

Lin

²

2015

Self Cite

View full text Add to dashboard Cite

In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.

show abstract

“…To reduce light scattering and improve three dimensional localization of excitation, the twophoton excitation (2PE) of tetrazoles was demonstrated with the naphthalene-based derivatives [34]. By taking advantage of the known 2PE of naphthalene [35], various naphthalene-based tetrazole derivatives were synthesized and tested (57)(58)(59) (Fig.…”

Section: Effects Of Substrates On Photoactivation Wavelength and Specmentioning

confidence: 99%

Photo-Triggered Click Chemistry for Biological Applications

Herner¹,

Qi²

2015

Cycloadditions in Bioorthogonal Chemistry

Self Cite

View full text Add to dashboard Cite

In the last decade and a half, numerous bioorthogonal reactions have been developed with a goal to study biological processes in their native environment, i.e., in living cells and animals. Among them, the photo-triggered reactions offer several unique advantages including operational simplicity with the use of light rather than toxic metal catalysts and ligands, and exceptional spatiotemporal control through the application of an appropriate light source with pre-selected wavelength, light intensity and exposure time. While the photoinduced reactions have been studied extensively in materials research, e.g., on macromolecular surface, the adaptation of these reactions for chemical biology applications is still in its infancy. In this chapter, we review the recent efforts in the discovery and optimization the photo-triggered bioorthogonal reactions, with a focus on those that have shown broad utility in biological systems. We discuss in each cases the chemical and mechanistic background, the kinetics of the reactions and the biological applicability together with the limiting factors.

show abstract

“…Among them, fluorescein [14], coumarin [15], rhodamine [16], FRET-based dyes [17], and so on, have attracted particular attention based on their excellent photophysical features. For an organic molecular photoactivatable probe, a caging group is usually adopted to protect the fluorophore and quench the fluorescence [18,19,20,21,22,23]. Under experimental conditions, the photosensitive bond is photocleaved by ultraviolet light (UV), resulting in the release of the caging group and recovery of fluorophore fluorescence.…”

Section: Introductionmentioning

confidence: 99%

ESIPT-Based Photoactivatable Fluorescent Probe for Ratiometric Spatiotemporal Bioimaging

Zhou

¹

,

Jiang

²

,

Zhao

³

et al. 2016

Sensors

View full text Add to dashboard Cite

Photoactivatable fluorophores have become an important technique for the high spatiotemporal resolution of biological imaging. Here, we developed a novel photoactivatable probe (PHBT), which is based on 2-(2-hydroxyphenyl)benzothiazole (HBT), a small organic fluorophore known for its classic luminescence mechanism through excited-state intramolecular proton transfer (ESIPT) with the keto form and the enol form. After photocleavage, PHBT released a ratiometric fluorophore HBT, which showed dual emission bands with more than 73-fold fluorescence enhancement at 512 nm in buffer and more than 69-fold enhancement at 452 nm in bovine serum. The probe displayed a high ratiometric imaging resolution and is believed to have a wide application in biological imaging.

show abstract

Fluorogenic, Two-Photon-Triggered Photoclick Chemistry in Live Mammalian Cells

Cited by 155 publications

References 24 publications

Photo-Triggered Click Chemistry for Biological Applications

Photo-Triggered Click Chemistry for Biological Applications

Photo-Triggered Click Chemistry for Biological Applications

ESIPT-Based Photoactivatable Fluorescent Probe for Ratiometric Spatiotemporal Bioimaging

Contact Info

Product

Resources

About