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S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds

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Chinese Chemical Letters 2024年第5期35卷 151-154页

作者： Ze-Yuan Ma Mei Xiao Cheng-Kun Li Adedamola Shoberu Jian-Ping Zou Key Laboratory of Organic Synthesis of Jiangsu Province College of Chemistry and Chemical EngineeringSoochow UniversitySuzhou 215123China

An efficient synthesis of the electrophilic reagent,S-(1,3-dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate(SDDP)is ***,the synthetic applications of SDDP wherein the transfer of the SP(O)(OEt)_(2) moiety occurs were *** this manner,SDDP underwent facile SP(O)(OEt)_(2) transfer with electron-rich substrates such as ketones,indoles,and thiols to formα-phosphorothiolated ketones,3-phosphorothiolated indoles and S-phosphorothiolated thioethers,respectively.

关键词： Electrophilic reagent phosphorothiolation Electrophilic substitution

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Regulating the properties of XQ-2d for targeted delivery of therapeutic agents to pancreatic cancers

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National Science Review 2023年第8期10卷 166-172页

作者： Qiuxia Yang Yongbo Peng Zhengyu Deng Dailiang Zhang Cheng-Yu Long Guo-Rong Zhang Juan Li Xue-Qiang Wang Weihong Tan Zhejiang Cancer Hospital Hangzhou Institute of Medicine(HIM) Chinese Academy of Sciences Molecular Science and Biomedicine Laboratory(MBL) State Key Laboratory of Chemo/Biosensing and ChemometricsCollege of Chemistry and Chemical Engineering College of Biology Aptamer Engineering Center of Hunan ProvinceHunan University Institute of Molecular Medicine(IMM) Renji HospitalSchool of MedicineCollege of Chemistry and Chemical Engineering Shanghai Jiao Tong University

Enhanced recognition ability, cell uptake capacity, and biostability are characteristics attributed to aptamer-based targeted anticancer agents, and are possibly associated with increased accumulation at the tumor site, improved therapeutic efficacy and reduced negative side effects. Herein, a phosphorothioate backbone modification strategy was applied to regulate the biomedical properties of pancreatic cancer cell–targeting aptamer for efficient in vivo drug delivery. Specifically, the CD71-targeting aptamer XQ-2d was modified into a fully thio-substituted aptamer S-XQ-2d, improving the plasma stability of S-XQ-2d and mitomycin C(MMC)-functionalized S-XQ-2d(MFSX), thus considerably prolonging their half-life in mice. Moreover, the binding and uptake capacities of S-XQ-2d were significantly enhanced. MFSX showed the same level of cytotoxicity as that of MMC against targeted cancer cells, but lower toxicity to non-targeted cells, highlighting its specificity and biosafety. Brief mechanistic studies demonstrated that XQ-2d and S-XQ-2d had different interaction modes and internalization pathways with the targeted cells.

关键词： phosphorothiolation MMC-functionalized aptamer targeted pancreatic cancer therapy

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