Cross‐linking chemistry and biology: development of multifunctional photoaffinity probes

Tomohiro, Takenori; Hashimoto, Makoto; Hatanaka, Y.

doi:10.1002/tcr.20058

Cited by 85 publications

(39 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently, bifunctional photoaffinity probes having ligand moiety and biotin-tag were used for cross-linking studies of ligand/receptor complex (31). However, the introduction of a highly polar and sterically congested biotin-anchored tag to an affinity compound often resulted in marked impairment of intrinsic biological activity in the crucial probe design step.…”

Section: Resultsmentioning

confidence: 99%

Selective and direct inhibition of TRPC3 channels underlies biological activities of a pyrazole compound

Kiyonaka

Kato

Nishida

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

342

318

View full text Add to dashboard Cite

Canonical transient receptor potential (TRPC) channels control influxes of Ca 2؉ and other cations that induce diverse cellular processes upon stimulation of plasma membrane receptors coupled to phospholipase C (PLC). Invention of subtype-specific inhibitors for TRPCs is crucial for distinction of respective TRPC channels that play particular physiological roles in native systems. Here, we identify a pyrazole compound (Pyr3), which selectively inhibits TRPC3 channels. Structure-function relationship studies of pyrazole compounds showed that the trichloroacrylic amide group is important for the TRPC3 selectivity of Pyr3. Electrophysiological and photoaffinity labeling experiments reveal a direct action of Pyr3 on the TRPC3 protein. In DT40 B lymphocytes, Pyr3 potently eliminated the Ca 2؉ influx-dependent PLC translocation to the plasma membrane and late oscillatory phase of B cell receptorinduced Ca 2؉ response. Moreover, Pyr3 attenuated activation of nuclear factor of activated T cells, a Ca 2؉ -dependent transcription factor, and hypertrophic growth in rat neonatal cardiomyocytes, and in vivo pressure overload-induced cardiac hypertrophy in mice. These findings on important roles of native TRPC3 channels are strikingly consistent with previous genetic studies. Thus, the TRPC3-selective inhibitor Pyr3 is a powerful tool to study in vivo function of TRPC3, suggesting a pharmaceutical potential of Pyr3 in treatments of TRPC3-related diseases such as cardiac hypertrophy.Ca 2ϩ signaling ͉ pyrazole compounds ͉ TRPC channels ͉ TRPC3

show abstract

Section: Resultsmentioning

confidence: 99%

Selective and direct inhibition of TRPC3 channels underlies biological activities of a pyrazole compound

Kiyonaka

Kato

Nishida

et al. 2009

Proc. Natl. Acad. Sci. U.S.A.

342

318

View full text Add to dashboard Cite

show abstract

“…These approaches are based on the affinity between the ligand and the target protein (Figure 1). Several reviews are published for the recent applications of photoaffinity labeling (Tomohiro et al, 2005;Hashimoto & Hatanaka, 2008).…”

Section: Photoaffinity Labelingmentioning

confidence: 99%

Selective Hydrogenation and Transfer Hydrogenation for Post-Functional Synthesis of Trifluoromethylphenyl Diazirine Derivatives for Photoaffinity Labeling

Hashimoto¹,

Murai²,

Holman³

et al. 2012

Hydrogenation

Self Cite

View full text Add to dashboard Cite

Elucidation of protein functions on the basis of structure–activity relationships can reveal the mechanisms of homeostasis functions in life and is one of the greatest interests of scientists. In the human body, many proteins are activated and/or inactivated by ligands to maintain homeostasis. Understanding the mechanism of molecular interactions between small bioactive ligands and proteins is an important step in rational drug design and discovery. ! Photoaffinity labeling, which is one of the most familiar approaches for chemical biology analysis, was initiated using diazocarbonyl derivatives in 1962 (Singh et al., 1962). Many researchers have subsequently tried to establish alternative approaches for the direct identification of target proteins for the bioactive small ligands. These approaches are based on the affinity between the ligand and the target protein (Figure 1). Several reviews are published for the recent applications of photoaffinity labeling (Tomohiro et al., 2005; Hashimoto & Hatanaka, 2008). To archive photoaffinity labeling, researchers have to prepare photoaffinity labeling ligands. The native ligands must be modified by photoreactive compounds (photophores) by organic synthesi

show abstract

“…The use of the (3-trifluoromethyl)phenyldiazirinyl (TPD) group as a photoreactive group in photoaffinity labeling confers selectivity for probe activation without damaging the peptides and proteins under radiation of 350 nm wavelength [48,52,53]. The strategy for the synthesis of homophenylalanine or bis-homophenylalanine containing TPD moiety starts with the introduction of a TPD moiety in anisole 71 into an aspartic acid analogue 66a [48] or a glutamic acid analogue 66b [46] (Scheme 6b).…”

Section: Forced Conditionsmentioning

confidence: 99%

Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions

et al. 2017

Self Cite

View full text Add to dashboard Cite

Trifluoromethanesulfonic acid (TfOH) is one of the superior catalysts for acylation. The catalytic activity of TfOH in C-and/or O-acylation has broadened the use of various substrates under mild and neat or forced conditions. In this review, the salient catalytic features of TfOH are summarized, and the unique controllability of its catalytic activity in the tendency of C-acylation and/or O-acylation is discussed.

show abstract

Cross‐linking chemistry and biology: development of multifunctional photoaffinity probes

Cited by 85 publications

References 39 publications

Selective and direct inhibition of TRPC3 channels underlies biological activities of a pyrazole compound

Selective and direct inhibition of TRPC3 channels underlies biological activities of a pyrazole compound

Selective Hydrogenation and Transfer Hydrogenation for Post-Functional Synthesis of Trifluoromethylphenyl Diazirine Derivatives for Photoaffinity Labeling

Trifluoromethanesulfonic Acid as Acylation Catalyst: Special Feature for C- and/or O-Acylation Reactions

Contact Info

Product

Resources

About