2015
DOI: 10.1021/bc500559e
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Third Generation Photo-Cross-Linked Small-Molecule Affinity Matrix: A Photoactivatable and Photocleavable System Enabling Quantitative Analysis of the Photo-Cross-Linked Small Molecules and Their Target Purification

Abstract: The third generation of photoactivatable beads designed to capture bioactive small molecules in a chemo- and site-nonselective manner upon irradiation at 365 nm of UV light and release them as coumarin conjugates after exposure to UV light of 302 nm is described. These photoactivatable and photocleavable beads enable quantification of the amount and distribution of immobilized small molecules prior to the pull-down experiments to identify target protein(s) for the immobilized small molecules. The newly develop… Show more

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Cited by 23 publications
(24 citation statements)
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“…As shown in Figure and Figure S1, after the completion of the reaction, unreacted volatile linkers 6 and/or by‐products of linker 6 were readily removed under vacuum as indicated by 1 H NMR analysis. Consistent with the carbene chemistry, at a concentration as high as 5 equiv relative to 1‐(2,4‐dihydroxyphenyl)ethan‐1‐one, linker 6 did not touch the azide functional group (Table S2). Trace amounts of remaining linker 6 were shown to have no interference with the subsequent DNA conjugation by CuAAC‐based click chemistry and enzymatic DNA ligation.…”
Section: Resultssupporting
confidence: 54%
See 1 more Smart Citation
“…As shown in Figure and Figure S1, after the completion of the reaction, unreacted volatile linkers 6 and/or by‐products of linker 6 were readily removed under vacuum as indicated by 1 H NMR analysis. Consistent with the carbene chemistry, at a concentration as high as 5 equiv relative to 1‐(2,4‐dihydroxyphenyl)ethan‐1‐one, linker 6 did not touch the azide functional group (Table S2). Trace amounts of remaining linker 6 were shown to have no interference with the subsequent DNA conjugation by CuAAC‐based click chemistry and enzymatic DNA ligation.…”
Section: Resultssupporting
confidence: 54%
“…Carbenes, nitrenes, and radicals are highly reactive chemical species that could chemo‐ and site‐nonselectively insert into any organic compound . Diazirines are widely used carbene generators, as three‐membered unsaturated heterocycles featuring an azo group and an sp 3 ‐hybridized carbon atom .…”
Section: Introductionmentioning
confidence: 99%
“…Silicon and silicon nitride surfaces can be similarly functionalized. 31 TPD groups have also been used on surfaces to capture small molecule reaction products 4 and drug molecules, 32 and have been incorporated into polymer crosslinkers that can be used to strengthen woven polyethylene fabric 5 or provide adhesion between polypropylene or polyethylene surfaces ( Fig. 1e ).…”
Section: Introductionmentioning
confidence: 99%
“…Exciting developments should also settle or find their way in the epigenetics field, expanding the proteomics toolbox to study drug action and protein complex composition. For instance, the possibility to photo-cross-link inhibitors to beads without the need to synthesize linkable analogues is a promising approach [ 121 ] which could render pulldowns a routine characterization tool after any phenotypic screen. Another expansion of the toolbox is an approach based on the successful combination of cellular thermal shift assays (CETSA) and bottom-up proteomics [ 122 , 123 ].…”
Section: Discussionmentioning
confidence: 99%