Photoaffinity labeling studies of the carbohydrate-binding proteins with different affinities

Sakurai, Kaori; Ozawa, Shutaro; Yamaguchi, Tamayo

doi:10.1016/j.bmc.2015.07.065

Cited by 7 publications

(4 citation statements)

References 23 publications

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“…Longer reaction times yielded less product. The results are consistent with our previous studies that showed that PAL reactions with alkyl diazirine are apparently complete after ten minutes –. On the other hand, the lower yields of 1 for reaction times of over ten minutes suggested that the alkyne group of the probe‐crosslinked BSA may be either destroyed by the prolonged UV irradiation or by reactive intermediates derived from the diazirine group.…”

Section: Methodssupporting

confidence: 92%

Two‐Step Synthesis of a Clickable Photoaffinity Probe from an Anticancer Saponin OSW‐1 and its Photochemical Reactivity

et al. 2016

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OSW-1 is ah ighly potent anticancer saponin with an unknown mechanism of action that is distinct from the currently used chemotherapeutic agents. To ward investigation of its binding proteins, we designed and synthesized ac lickable photoaffinity probe from OSW-1 and characterized its photochemical reactivity.Amild, twostep procedure involving aM e 2 SnCl 2 -mediated acylation reaction was developed to site-selectively derivatize OSW-1w ith al inker that bears ap hotoreactive group and an alkyne tag. The OSW-1-basedp hotoaffinity probe retained potent anticancer activity similar to that of the parent natural product, thereby providing ac ell-permeable analogue of OSW-1. Photoaffinity labeling studies demonstrated that the probe enabled crosslinking of am odel sterolbinding protein in an affinity-dependent fashion,w hich could be efficiently detected by conjugating afluorophore or biotin by click chemistry.

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Section: Methodssupporting

confidence: 92%

Two‐Step Synthesis of a Clickable Photoaffinity Probe from an Anticancer Saponin OSW‐1 and its Photochemical Reactivity

et al. 2016

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“…Photoaffinity labeling (PAL) is a complementary chemical proteomics technique, it provides a new idea for exploring the targets of already marketed drugs acting on COVID‐19 (Pala et al, 2020; Smith & Collins, 2015). By irradiating light at a specific wavelength, the photoreactive group immediately forms a reaction intermediate and covalently crosslinks to the target protein, and the target protein is explored to react to form reactive intermediates and covalently cross‐link with the target protein by this analysis method (Figure 2) (Das, 2019; Fallon et al, 2021; Sakurai et al, 2015). Photoaffinity groups in photoaffinity probes include diaziridine, tetrazole, benzophenone, and the like.…”

Section: Introductionmentioning

confidence: 99%

Identification of potential targets against SARS‐CoV‐2 of antiviral drugs based on photoaffinity probes

Wang

Pan

et al. 2023

Drug Development Research

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Facing the sudden outbreak of coronavirus disease 2019 (COVID‐19), it is extremely urgent to develop effective antiviral drugs against severe acute respiratory syndrome coronavirus 2 (SARS‐CoV‐2). Drug repurposing is a promising strategy for the treatment of COVID‐19. To identify the precise target protein of marketed medicines, we initiate a chemical biological program to identify precise target of potential antivirus drugs. In this study, two types of recombinant human coronavirus SARS‐CoV‐2 RdRp protein capturing probes with various photoaffinity labeling units were designed and synthesized based on the structure of FDA‐approved drugs stavudine, remdesivir, acyclovir, and aladenosine. Fortunately, it was found that one novel photoaffinity probe, RD‐1, could diaplayed good affinity with SARS‐CoV‐2 RdRp around the residue ARG_553. In addition, RD‐1 probe also exhibited potent inhibitory activity against 3CLpro protease. Taken together, our findings will elucidate the structural basis for the efficacy of marketed drugs, and explore a rapid and efficient strategy of drug repurposing based on the identification of new targets. Moreover, these results could also provide a scientific basis for the clinical application of marketed drugs.

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“…19,20 Photoaffinity labeling is able to capture transient and low affinity interactions, and has been previously combined with metabolic oligosaccharide engineering to profile interactions with glycoconjugates. [21][22][23][24][25] To enable identification of potential HMObinding proteins, we chose to utilize a 'fully-functionalized' enrichment tag composed of a photoactivatable diazirine group for UV light-induced capture of HMO bound protein targets and an alkyne handle for conjugation to azide-bearing reporter tags via copper-mediated azide-alkyne (CuAAC) ''click'' chemistry. 26,27 We synthesized four probes composed of the most abundant HMOs in human breast milk (lactose or Lac, 2'fucosyl lactose or 2FL, 3'sialyl lactose or 3SL, and 6'sialyl lactose or 6SL), and first cross-evaluated their engagement with purified glycan-binding lectins in vitro, followed by profiling their interactions with live murine macrophages.…”

Section: Introductionmentioning

confidence: 99%

Chemoproteomic mapping of human milk oligosaccharide (HMO) interactions in cells

et al. 2022

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Photoaffinity labeling studies of the carbohydrate-binding proteins with different affinities

Cited by 7 publications

References 23 publications

Two‐Step Synthesis of a Clickable Photoaffinity Probe from an Anticancer Saponin OSW‐1 and its Photochemical Reactivity

Two‐Step Synthesis of a Clickable Photoaffinity Probe from an Anticancer Saponin OSW‐1 and its Photochemical Reactivity

Identification of potential targets against SARS‐CoV‐2 of antiviral drugs based on photoaffinity probes

Chemoproteomic mapping of human milk oligosaccharide (HMO) interactions in cells

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