3-Benzoylquinoxalinone as a photoaffinity labelling derivative with fluorogenic properties allowing reaction monitoring under “no-wash” conditions

Cauwel, Madeleine; Guillou, C. Le; Renault, Kévin; Schapman, Damien; Bénard, Magalie; Galas, Ludovic; Cosette, Pascal; Renard, Pierre; Sabot, Cyrille

doi:10.1039/d1cc01072g

Cited by 10 publications

(5 citation statements)

References 23 publications

(24 reference statements)

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“…For instance, Murale et al reported the synthesis and application of a BODIPY bearing a modified benzophenone motif for protein functionalization . Recent reports have also explored the use of photochemistry to produce radioactive mAbs for positron emission tomography (PET) imaging − and photoactivatable fluorophores for protein labeling and live cell tracking. − …”

Section: Introductionmentioning

confidence: 99%

Photoactivatable Fluorescent Tags for Dual-Modality Positron Emission Tomography Optical Imaging

et al. 2022

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Fluorescent protein conjugates are vital tools in a wide range of scientific disciplines from basic biochemical research to applications in clinical pathology and intraoperative surgery. We report the synthesis and characterization of photoactivatable fluorophores (PhotoTags) based on the functionalization of coumarin, fluorescein, BODIPY, rhodamine B, and cyanine dyes with a photochemically active aryl azide group. Photochemical labeling experiments using human serum albumin produced fluorescent proteins in high yields under irradiation with ultraviolet light for <15 min. We also synthesized DFO-RhodB-PEG 3 -ArN 3  a photoactivatable compound that can be radiolabeled with 89 Zr for applications in optical imaging and positron emission tomography. One-pot 89 Zr-radiolabeling and light-induced protein conjugation produced [ 89 Zr]ZrDFO-RhodB-PEG 3 -azepin-trastuzumab. Proofof-concept studies in vitro and in vivo confirmed that [ 89 Zr]ZrDFO-RhodB-PEG 3 -azepin-trastuzumab is a potential dual-modality agent for detecting human epidermal growth factor receptor 2 (HER2/neu) expression. Overall, the PhotoTag technology represents a rapid, synthetically versatile, and user-friendly approach for generating novel protein conjugates.

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Section: Introductionmentioning

confidence: 99%

Photoactivatable Fluorescent Tags for Dual-Modality Positron Emission Tomography Optical Imaging

et al. 2022

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“…We continue to investigate the speculation that multiple proteins tagged with arylchloro-pcBD may be involved in cellular GSH transport mechanisms. Sabot et al designed similar benzophenone-mimetic fluorogenic probes (Figure A) . They presented 3-benzoylquinoxalinone probes that labeled proteins via the Norrish Type I diradical generation mechanism using visible blue LED irradiation instead of UV excitation limited to in vitro conditions.…”

Section: Multifunctional Photo-cross-linkermentioning

confidence: 99%

“…Sabot et al designed similar benzophenone-mimetic fluorogenic probes (Figure 5A). 46 They presented 3-benzoylquinoxalinone probes that labeled proteins via the Norrish Type I diradical generation mechanism using visible blue LED irradiation instead of UV excitation limited to in vitro conditions.…”

Section: Fluorogenic Photo-cross-linkers For Bioimagingmentioning

confidence: 99%

Multifunctional Photo-Cross-Linking Probes: From Target Protein Searching to Imaging Applications

et al. 2022

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“…Fluorogenic 3‐benzoylquinoxalin‐2(1 H )‐ones 169 were recently employed by our team as photoreactive moieties in the design of photoaffinity probes (Scheme 24). [67] Photoaffinity labelling generally relies on the use of photoreactive functions including benzophenones, diazirines or phenylazides, which generate highly reactive species able to covalently bind protein target in response to light activation. As previously mentioned, (c.f.…”

Section: Applicationsmentioning

confidence: 99%

Quinoxalin‐2(1H)‐ones: Chemical Synthesis, Fluorescence Properties and Applications

2022

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Photophysical properties of quinoxalin-2(1H)-ones have long been neglected, in particular compared with those of coumarins, their oxygenated counterparts, despite their complementarity in terms of absorbance and fluorescence windows. This review provides first an overview of the synthesis of quinoxalin-2(1H)-ones, focusing on the most recent contributions. Fluorescence properties of quinoxalin-2(1H)-ones and of their π-extended derivatives are tackled through the description of a series of examples and applications, including chemosensing and biosensing. www.eurjoc.org

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3-Benzoylquinoxalinone as a photoaffinity labelling derivative with fluorogenic properties allowing reaction monitoring under “no-wash” conditions

Abstract: Described herein is a compact benzophenone-quinoxalinone photoaffintiy labelling hybrid system with caged fluorescence properties. Upon visible blue LED irradiation (λmax 450 nm), this photo-crosslinker is able to covalently capture proteins...

Cited by 10 publications

References 23 publications

Photoactivatable Fluorescent Tags for Dual-Modality Positron Emission Tomography Optical Imaging

Photoactivatable Fluorescent Tags for Dual-Modality Positron Emission Tomography Optical Imaging

Multifunctional Photo-Cross-Linking Probes: From Target Protein Searching to Imaging Applications

Quinoxalin‐2(1H)‐ones: Chemical Synthesis, Fluorescence Properties and Applications

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