School of Materials Science and Engineering, Central South University, Changsha, Hunan, 410083, China.
School of Chemistry, University of Birmingham, Edgbaston, Birmingham, B15 2TT, UK.
Angew Chem Int Ed Engl. 2020 Feb 3;59(6):2284-2288. doi: 10.1002/anie.201912555. Epub 2019 Dec 27.
Photochemical ligation is important in biomaterials engineering for spatiotemporal control of biochemical processes. Such reactions however generally require activation by high energy UV or short wavelength blue light, which can limit their use as a consequence of the potential of these high energy light sources to damage living cells. Herein, we present an additive-free, biocompatible, chemical ligation triggered by mild visible light. BODIPY dyes with a pendant thioether attached at the meso-position undergo photolysis of the [C-S] bond under green light (λ=530 nm) excitation, producing an ion pair intermediate that can react specifically with a propiolate group. The utility of this photochemical ligation in materials science is demonstrated by the fabrication of hydrogels with specific architectures, photo-immobilization of biomacromolecules, and live cell encapsulation within a hydrogel scaffold.
光化学连接在生物材料工程中对于时空控制生化过程非常重要。然而,这些反应通常需要高能 UV 或短波长蓝光激活,由于这些高能光源有可能损害活细胞,因此限制了它们的使用。在此,我们提出了一种无添加剂、生物相容的、由温和可见光引发的化学连接。带有侧基硫醚的 BODIPY 染料在绿光(λ=530nm)激发下发生[C-S]键的光解,生成可以与丙炔酸酯基团特异性反应的离子对中间体。这种光化学连接在材料科学中的应用通过具有特定结构的水凝胶的制备、生物大分子的光固定以及水凝胶支架内活细胞的包封得到了证明。