d-type peptides based fluorescent probes for "turn on" sensing of heparin

In this study, seven TPE-1 derived fluorescent probes were rationally designed, efficiently synthesized and evaluated. The stability and water solubility were systematically estimated. Especially, to achieve real-time monitoring of proteolytic stability, the novel Abz/Dnp-based "turn on" probes that employ the internally quenched fluorescent (IQF) mechanism were designed and synthesized. Moreover, the detection ability of synthetic fluorescent probes for heparin were systematically evaluated. Importantly, the performance of d-type peptide fluorescent probe XH-6 indicated that d-type amino acid substitutions could significantly improve the proteolytic stability without compromising its ability of heparin sensing, and attaching solubilizing tag 2-(2-aminoethoxy) ethoxy) acid (AEEA) could greatly enhance the solubility. Collectively, this study not only established practical strategies to improve both the water solubility and proteolytic stability of "turn on" fluorescent probes for heparin sensing, but also provided valuable references for the subsequent development of enzymatic hydrolysis-resistant d-type peptides based fluorescent probes.PMID:38604021 | DOI:10.1016/j.bioorg.2024.107356

Source: Bioorganic Chemistry - April 11, 2024 Category: Chemistry Authors: Huan Xu Xing-Yan Fu Yong-Xin Bao Shu-Ya Zhu Zi Xu Min Song Yun-Kun Qi Zhibo Li Shan-Shan Du Source Type: research