Development and Leading-Edge Application of Innovative Photoaffinity Labeling

Hatanaka, Y.

doi:10.1248/cpb.c14-00645

Cited by 50 publications

(30 citation statements)

References 83 publications

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“…Benzophenones, aryl azides, and diazirines are the most commonly used probes in photoaffinity labeling studies . We therefore designed and prepared two new photoaffinity‐labeled analogs, azide‐TRAP ( 1 ) and diazirine‐TRAP ( 2 ) of CrAsH‐EDT 2 , which are shown in Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT₂ Photoaffinity Probes

Syeda

Rice

Hook

et al. 2016

Archiv der Pharmazie

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Two photo‐crosslinking biarsenical (CrAsH‐EDT2)‐modified probes were synthesized that are expected to be useful tools for tetracysteine‐labeled proteins to facilitate the co‐affinity purification of their DNA binding sequences and interacting proteins. In addition, improvements for the synthesis of CrAsH‐EDT2 and N 1‐(4‐azido‐2‐nitrophenyl)hexane‐1,6‐diamine are reported. Both photoprobes effectively entered HeLa cells (and the nucleus) and were dependent on the tetracysteine motif in recombinant DMRT1 (doublesex and Mab3‐related transcription factor) to induce fluorescence, suggesting that their crosslinking abilities can be exploited for the identification of nucleic acids and proteins associated with a protein of interest.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT₂ Photoaffinity Probes

Syeda

Rice

Hook

et al. 2016

Archiv der Pharmazie

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“…These double-input systems 27 share conceptual similarities with photoaffinity labels. 28 Na + binding in the benzocrown causes further suppression of PET 3 but the reduced hydrophobicity shifts the PET pair to a position of higher polarity 13 which accelerates PET. 9 The nett effect on fluorescence depends on the nature of the protein (Fig.…”

Section: It Is Clear Frommentioning

confidence: 99%

Lighting-up protein–ligand interactions with fluorescent PET (photoinduced electron transfer) sensor designs

et al. 2018

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“…Photoaffinity labeling [ 7 , 8 , 9 , 10 ] is a useful biochemical method for the analysis of biological interactions between low-molecular-weight bioactive compounds and biomolecules. The methodology may afford other information near the binding sites which cannot be obtained from structure–activity relationship studies.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

et al. 2020

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Lactisole, which has a 2-phenoxy propionic acid skeleton, is well-known as an inhibitor of sweet taste receptors. We recently revealed some of the structure–activity relationships of the aromatic ring and chiral center of lactisole. Photoaffinity labeling is one of the common chemical biology methods to elucidate the interaction between bioactive compounds and biomolecules. In this paper, the novel asymmetric synthesis of lactisole derivatives with common photophores (benzophenone, azide and trifluoromethyldiazirine) for photoaffinity labeling is described. The synthetic compounds are subjected to cell-based sweet taste receptors, and the substitution with trifluoromethyldiazirinyl photophore shows the highest affinity to the receptor of the synthesized compounds.

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Development and Leading-Edge Application of Innovative Photoaffinity Labeling

Cited by 50 publications

References 83 publications

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT₂ Photoaffinity Probes

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT₂ Photoaffinity Probes

Lighting-up protein–ligand interactions with fluorescent PET (photoinduced electron transfer) sensor designs

Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

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Development and Leading-Edge Application of Innovative Photoaffinity Labeling

Cited by 50 publications

References 83 publications

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT2 Photoaffinity Probes

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT2 Photoaffinity Probes

Lighting-up protein–ligand interactions with fluorescent PET (photoinduced electron transfer) sensor designs

Asymmetric Synthesis of Photophore-Containing Lactisole Derivatives to Elucidate Sweet Taste Receptors

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Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT₂ Photoaffinity Probes

Synthesis of Arylazide‐ and Diazirine‐Containing CrAsH‐EDT₂ Photoaffinity Probes