Department of Medicinal Chemistry, College of Pharmacy, University of Florida, Gainesville, Florida 32610, United States.
UF Health Cancer Center, University of Florida, Gainesville, Florida 32610, United States.
J Am Chem Soc. 2020 Sep 9;142(36):15575-15584. doi: 10.1021/jacs.0c07594. Epub 2020 Aug 31.
"Smart" biomaterials that are responsive to physiological or biochemical stimuli have found many biomedical applications for tissue engineering, therapeutics, and molecular imaging. In this work, we describe polymerization of activatable biorthogonal small molecules in response to a reducing environment change . We designed a carbohydrate linker- and cyanobenzothiazole-cysteine condensation reaction-based small molecule scaffold that can undergo rapid condensation reaction upon physiochemical changes (such as a reducing environment) to form polymers (pseudopolysaccharide). The fluorescent and photoacoustic properties of a fluorophore-tagged condensation scaffold before and after the transformation have been examined with a dual-modality optical imaging method. These results confirmed the polymerization of this probe after both local and systemic administration in living mice.
“智能”生物材料对生理或生化刺激有响应,已在组织工程、治疗和分子成像等多个医学领域得到广泛应用。在这项工作中,我们描述了在还原环境变化下可响应的活化双正交小分子的聚合反应。我们设计了一种基于碳水化合物连接子和氰基苯并噻唑-半胱氨酸缩合反应的小分子支架,该支架可在物理化学变化(如还原环境)下快速发生缩合反应,形成聚合物(假多糖)。我们使用双模态光学成像方法检查了荧光标记缩合支架在转化前后的荧光和光声性质。这些结果证实了该探针在活体小鼠局部和全身给药后的聚合反应。