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Boronic acids (BA) are able to reversibly interact with the diol groups, a commonly found motif in biomolecules including sugars, ribose and catechols. In some aspects, they optimally enhance the environmental stability of ribose, supporting a rationale for the "RNA world hypothesis," one of the theories of the origin of life. For their carbohydrate-binding properties, they can be regarded as a synthetic mimic of lectins, often termed “borono-lectins”. Remarkably, the borono-lectins platform can be chemically tailored to manifest a broad profile of binding strength and specificity. Besides the structural versatility, a pronounced change in water solubility accompanies some molecular-recognition events, enabling the "borono-lectins" to enjoy their complex and hierarchical functionalities. This feature, when combined with amphiphilic polymeric backbones, translates into many creative principles for fine-tuning or switching the hydration and more complex molecular assemblies in a way interactive with biology. I will provide a brief overview of our recent efforts on the related applications with focuses on smart insulin delivery systems^1-4 and sialic acid detections relevant to cancer diagnosis and treatment^5-7 among others.