Cyclic Thiosulfinates as a Novel Class of Disulfide Cleavable Cross-Linkers for Rapid Hydrogel Synthesis,Bioconjugate Chemistry

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Cyclic Thiosulfinates as a Novel Class of Disulfide Cleavable Cross-Linkers for Rapid Hydrogel Synthesis
Bioconjugate Chemistry ( IF 4.0 ) Pub Date : 2021-02-19 , DOI: 10.1021/acs.bioconjchem.1c00049
Krishna C Aluri _{1,

2} , Md Amin Hossain _{1,

2} , Ninad Kanetkar ₃ , Brandon C Miller ₁ , Matthew G Dowgiallo ₁ , Durgalakshmi Sivasankar _{1,

2} , Matthew R Sullivan ₄ , Roman Manetsch _{1,

4} , Tania Konry ₄ , Adam Ekenseair ₃ , Jeffrey N Agar _{1,

2,

4}

Affiliation

We recently reported that cyclic thiosulfinates are cysteine selective cross-linkers that avoid the “dead-end” modifications that contribute to other cross-linkers’ toxicity. In this study, we generalize the chemistry of cyclic thiosulfinates to that of thiol selective cross-linking and apply them to the synthesis of hydrogels. Thiol-functionalized four-arm poly(ethylene glycol) and hyaluronic acid monomers were cross-linked with 1,2-dithiane-1-oxide to form disulfide cross-linked hydrogels within seconds. The synthesized hydrogel could be reduced with physiological concentrations of glutathione, which modulated hydrogel mechanical properties and degradation kinetics. Bovine serum albumin protein was successfully encapsulated in hydrogel, and diffusion-mediated release was demonstrated in vitro. Hep G2 cells grew in the presence of preformed hydrogel and during hydrogel synthesis, demonstrating acceptable cytotoxicity. We encapsulated cells within a hydrogel and demonstrated cell growth and recovery up to 10 days, with and without cell adhesion peptides. In summary, we report cyclic thiosulfinates as a novel class of cross-linkers for the facile synthesis of biodegradable hydrogels.

中文翻译：

环状硫代亚磺酸盐作为用于快速水凝胶合成的新型二硫化物可裂解交联剂

我们最近报道，环状硫代亚磺酸盐是半胱氨酸选择性交联剂，可避免导致其他交联剂毒性的“死胡同”修饰。在这项研究中，我们将环状硫代亚磺酸盐的化学概括为硫醇选择性交联的化学，并将它们应用于水凝胶的合成。硫醇官能化的四臂聚（乙二醇）和透明质酸单体与 1,2-二噻烷-1-氧化物交联，在几秒钟内形成二硫化物交联水凝胶。合成的水凝胶可以通过生理浓度的谷胱甘肽还原，从而调节水凝胶的机械性能和降解动力学。牛血清白蛋白成功地封装在水凝胶中，并在体外证明了扩散介导的释放。Hep G2 细胞在预制水凝胶存在下和在水凝胶合成过程中生长，显示出可接受的细胞毒性。我们将细胞封装在水凝胶中，并证明了细胞生长和恢复长达 10 天，无论有无细胞粘附肽。总之，我们报告了环状硫代亚磺酸盐作为一类新型交联剂，可用于轻松合成可生物降解的水凝胶。

更新日期：2021-03-17

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