New photocleavable linker: α-Thioacetophenone-type linker

Yonezawa, Hirotaka; Nishiyama, Yoshitake; Iwatsubo, Takeshi; Tomita, Taisuke; Yokoshima, Satoshi; Fukuyama, Tohru

doi:10.1016/j.bmcl.2014.04.104

Cited by 7 publications

(7 citation statements)

References 26 publications

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“…Azobenzene, 87 disulfide, 86 photocleavable nitrophenyl 86 and α-thioacetophenone, 88 vicinal diol 89 and acid cleavable dialkoxydiphenylsilane-90 tags have been successfully employed for this purpose. This has been particularly useful in studying posttranslational modifications (PMTs) by fatty acids, such as S-palmitoylation on cysteine residues that are critical for function and targeting of membrane proteins.…”

Section: Cleavable Ms-based Pull-down Probesmentioning

confidence: 99%

Chemical Methods for Probing Virus–Host Proteomic Interactions

et al. 2016

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Interactions between host and pathogen proteins constitute an important aspect of both infectivity and the host immune response. Different viruses have evolved complex mechanisms to hijack host-cell machinery and metabolic pathways to redirect resources and energy flow toward viral propagation. These interactions are often critical to the virus, and thus understanding these interactions at a molecular level gives rise to opportunities to develop novel antiviral strategies for therapeutic intervention. This review summarizes current advances in chemoproteomic methods for studying these molecular altercations between different viruses and their hosts.

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Section: Cleavable Ms-based Pull-down Probesmentioning

confidence: 99%

Chemical Methods for Probing Virus–Host Proteomic Interactions

et al. 2016

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“…The aqueous layer was then extracted with DCM (3 × 15 ml). The combined organic layer was dried over Na 2 SO 4 , filtered and concentrated to provide pure title compounds 17 .…”

Section: General Procedures 2: Preparation Of Thiols 19a–cmentioning

confidence: 99%

Design, synthesis, and biological evaluation of novel derivatives of dithiodiglycolic acid prepared via oxidative coupling of thiols

Bakulina

Bannykh

Jovanović

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

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Human thioredoxin reductase 1 (TrxR1) is a selenocysteine-containing enzyme which plays a crucial role in regulating numerous redox signalling pathways within the cell. While its functioning is important in all cells, levels of TrxR1 expression are higher in cancer cells, possibly as an adaptation to much higher levels of reactive oxygen species and the need for more extensive DNA synthesis. This makes TrxR1 an attractive target for cancer therapy development. Inspired by the structure of disulphide compounds which have advanced through various stages of clinical development, we designed a series of dithiodiglycolic acid derivatives. These were prepared from respective thiol synthons using an iodine- or benzotriazolyl chloride-promoted oxidative disulphide bond formation. Inhibition of TrxR present in cell lysates from human neuroblastoma cells (SH-SY5Y) and rat liver cells indicated several compounds with a potential for TrxR inhibition. Some of these compounds were also tested for growth inhibition against two human cancer cell lines and normal human keratinocytes.

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“…Spin ultrafilters (vivaspin 500) were purchased from GE Healthcare. 1 H and 13 C NMR spectra were recorded on Bruker instruments (400 or 500 MHz for 1 H and 100 or 125 MHz for 13 C). MS data were collected with AQUITY UPLC from Waters.…”

Section: Generalmentioning

confidence: 99%

“…1 H NMR (500 MHz, CD 3 OD) δ = 7.81 (d, J = 8.4 Hz, 2H), 7.51 (d, J = 8.1 Hz, 2H), 5.43 (s, 1H), 3.32 (s, 6H). 13…”

Section: Acetal 1 30mentioning

confidence: 99%

“…Long-wave UV light can be used to release photocleavable linkers, but in some conditions, illumination of the sample is limited. [11][12][13] There is also an acid labile linker from Pierce ( proprietary structure) that is cleaved in 95% TFA. Another alternative is a dialkoxydiphenylsilane linker invented by Szychowski et al that is reported to be efficiently cleaved upon treatment with 10% formic acid for 0.5 h. 14 Other types of cleavable linkers 15,16 have been developed such as an enzymatically (TEV) cleaved linker, 17 diazobenzene-derived linkers that are cleaved with Na 2 S 2 O 4 , [18][19][20] vicinal diol linkers cleaved with NaIO 4 21 and linkers that are released upon reactions with nucleophiles including levulinoyl ester 22 and nitrobenzenesulfonamide.…”

Section: Introductionmentioning

confidence: 99%

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Cyclic acetals as cleavable linkers for affinity capture

et al. 2015

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Labeling proteins with biotin is a widely used method to identify target proteins due to biotin’s strong binding affinity for streptavidin. Combined with alkyne-azide cycloaddition, which enables the coupling of probes to targeted proteins, biotin tags linked to an alkyne or azide have become a powerful tool for purification and analysis of proteins in proteomics. However, biotin requires harsh elution conditions to release the captured protein from the bead matrix. Use of these conditions reduces signal to noise and complicates the analysis. To improve affinity capture, cleavable linkers have been introduced. Here, we demonstrate the use of a cyclic acetal biotin probe that is prepared easily from commercially available starting materials, is stable to cell lysates, yet is cleaved under mildly acidic conditions, and which provides an aldehyde for further elaboration of the protein, if desired.

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New photocleavable linker: α-Thioacetophenone-type linker

Cited by 7 publications

References 26 publications

Chemical Methods for Probing Virus–Host Proteomic Interactions

Chemical Methods for Probing Virus–Host Proteomic Interactions

Design, synthesis, and biological evaluation of novel derivatives of dithiodiglycolic acid prepared via oxidative coupling of thiols

Cyclic acetals as cleavable linkers for affinity capture

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