Shamis Marina, Shabat Doron
Department of Organic Chemistry, School of Chemistry, Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel.
Chemistry. 2007;13(16):4523-8. doi: 10.1002/chem.200700142.
Self-immolative dendrimers are a unique class of molecules that are able to disassemble upon undergoing a specific triggering reaction through domino-like fragmentations. We have designed and synthesized a novel AB(6) self-immolative dendritic adaptor that amplifies a single cleavage event into the release of six reporter units. The disassembly mechanism is based on a specifically triggered cleavage event followed by elimination of a cyclic urea derivative and six consecutive quinone methide eliminations. The system was disassembled under both organic and aqueous conditions by either chemical or enzymatic triggering. Various reporter molecules and triggering groups were introduced onto the dendritic adaptor to obtaining sensor molecules with enhanced properties for diagnostics and imaging.
自裂解树枝状大分子是一类独特的分子，它们能够通过类似多米诺骨牌式的碎片化反应在经历特定触发反应时发生拆解。我们设计并合成了一种新型的AB(6)自裂解树枝状适配体，它能将单次裂解事件放大为六个报告单元的释放。拆解机制基于特定触发的裂解事件，随后消除环状脲衍生物以及连续六次消除醌甲基化物。该体系在有机和水性条件下均可通过化学或酶促触发进行拆解。将各种报告分子和触发基团引入树枝状适配体上，以获得具有增强诊断和成像性能的传感器分子。
