Polyampholytes hydrogels have shown promise as functional biomaterial platforms with resistance to nonspecific protein adsorption (non-biofouling). However, there are very few zwitterionic cross-linkers to complement these materials. Integral to the understanding and development of such materials is the ability to reliably synthesize and modify the structural parameters of zwitterionic cross-linkers. The adaptability and variety of amino acids commercially available gives a great level of possible diversity in the construction of polypeptides with an imbedded zwitterionic component. Methacrylate functionalized serine-serine dipeptide cross-linkers gave enhanced non-fouling characteristics when compared to a poly(ethylene glycol) (PEG)-based cross-linker of similar chain length in a typical TMM:CAA hydrogel. Further expansion of our synthetic strategy has produced dimethacrylamides and mixed methacrylamide/methacrylates. Key to these routes is the selective protection of both N and C termini. In this presentation, the molecular-level control of our synthetic strategy extends to a variety of amine-terminated amino acids: DAP (diaminopropionic acid); DAB (diaminobutyric acid); and ornithine, as to highlight our addition/removal of carbon-chain spacers to provide directed cross-linker length.  Zwitterionic charge spacing, charge density, and additions of pendant sidechains are also adaptable to these syntheses and will be discussed.

Design of methacrylamide based zwitterionic cross-linkers for polyampholyte hydrogels

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