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The therapeutic landscape is transitioning from small-molecule drugs to biologics-based therapeutics including peptides, proteins, antibodies, and nucleic acids, due to their greater target specificity and lower toxicity. However, the delivery of these biologics remains a significant challenge. They are vulnerable to degradation, must overcome biological barriers, and require targeted delivery to specific cells/tissues. Our research program will devise new chemical strategies to confront these issues at the intersection of basic science and translational research. Specifically, we will develop chemical tools with modular scaffolds to address three independent yet interconnected projects: (i) reversible protein modification for in vivo protein-based drug delivery, (ii) fluorogenic nanoparticles to investigate the cellular uptake mechanism of biologics, and (iii) trifunctional activity-based probes for in vivo molecular imaging and new target discovery. Combining tunable chemical tools and high-throughput techniques, our group envisions a ‘bottom-up’ approach to solving fundamental challenges in biomedicine.