DNA-Compatible Photoredox Atom Transfer Radical Addition to Alkynes with Thiosulfonates

Open AccessCCS ChemistryRESEARCH ARTICLES23 Aug 2024DNA-Compatible Photoredox Atom Transfer Radical Addition to Alkynes with Thiosulfonates Cong Wang, Yinghui Lu, Zhiyuan Peng, Chi Zhang, Qingchao Liu, Xue-Qiang Wang and Tiezheng Jia Cong Wang , Yinghui Lu , Zhiyuan Peng , Chi Zhang , Qingchao Liu , Xue-Qiang Wang and Tiezheng Jia Cite this: CCS Chemistry. 2024;0:1–28https://doi.org/10.31635/ccschem.024.202404703 SectionsSupplemental MaterialAboutPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail With the blossom of DNA encoded library (DEL) and nucleic acid aptamers techniques, DNA-compatible reactions draw increasingly attention in both pharmaceutical industry and academia. In this regard, incorporation of organosulfur scaffolds on DNA via Csp2-S bond exhibits advantages but remains underrepresented. Herein, we report a mild and efficient photoredox atom transfer radical addition (ATRA) to terminal and internal alkynes with thiosulfonates catalyzed by organic photocatalyst, furnishing a wide array of E-β-arylthiol-vinyl sulfones with excellent regio- and stereoselectivity. Mechanistic investigations demonstrate that sulfonyl radical likely serves as the key intermediate in this transformation. Leveraging the broad functional group tolerance and the mild and bio-friendly conditions, this protocol could be adapted to simultaneously install sulfones and sulfides on DNA. More importantly, a redox responsive fluorescent probe (10-ethyl-2-sulfonate-acridone, ESAC) could be conveniently introduced on two commonly used aptamers (AS1411 and Sgc8c), allowing their subsequent imaging studies across a series of human tumor cell lines. Remarkably, the process of ESAC-aptamers entering the cells was captured by both the confocal microscopy and flow cytometry techniques, when most of the ESAC-aptamers exhibits green fluorescence after their cell uptake, but with a small portion stayed outside of the membrane emitting blue fluorescence. Download figure Download PowerPoint Previous articleNext article FiguresReferencesRelatedDetails Issue AssignmentNot Yet AssignedSupporting Information Copyright & Permissions© 2024 Chinese Chemical Society Downloaded 0 times PDF downloadLoading ...