Polymeric amphiphiles and their assemblies have been widely explored for applications ranging from nanocarriers for controlled drug delivery to nano-containers for green chemistry. Building upon accelerated synthetic approaches for the synthesis of dendritic amphiphiles, over the past few years, we used highly modular synthetic methodology to study how small changes in the hydrophobic dendron can affect the enzymatic responsiveness of micellar nanocarriers. To allow tracking of these enzyme-responsive nanocarriers, we have functionalized them with labeling dyes that allow the micellar nanocarriers to spectral report their enzymatic activation and disassembly inside complex biological media. In this talk, we will share our key findings as well as preliminary data on how the hydrophobicity of such micelles affects their function as micellar catalysts.