ost-synthesis modification of thermo-responsive hydrogels: Hydrazonecrosslinking ofα-oxoaldehyde obtained from NIPAm-based polymers

ROMERO, MARCELO R.; WOLFEL, ALEXIS; ALVAREZ IGARZABAL C

EUROPEAN POLYMER JOURNAL

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2019 vol. 112 p. 389 - 399

0014-3057

Currently, the chemistry of alpha-oxoaldehydes (α-oxo-ALD) is a versatile and useful tool in thefield of bio-conjugation of peptides and proteins. The combination of smart materials with biomolecules also represents animportant opportunity for the development of smart functional materials in a wide range of applications.However, the development of thermosensitive polymeric materials withα-oxo-ALD has not yet been reported.For this reason, the incorporation of these highly reactive functional groups in a thermo-responsive polymer by asuccessful protocol is reported in this work. Poly-N-isopropylacrylamide (p-NIPAm) functionalized withα-oxo-ALD (p-NIPAm-α-oxo-ALD) was obtained from precursor hydrogels (HGs) based on NIPAm crosslinked with(+)-N,N′-diallyltartramide (DAT). This crosslinker presents vicinal hydroxyl groups which can be cleaved withperiodate to yield nanoparticles (10?100 nm range) with pendantα-oxo-ALD groups. Furthermore, the p-NIPAm-α-oxo-ALD product obtained was used to synthesize novel thermo-responsive hydrogels by its reaction withadipic acid dihydrazide (AADH). Then, the formation of hydrazone bonds at different pHs and the effect ofthermal transition of p-NIPAm on the gelation were studied. The developed protocol may be fully investigated asa platform to obtain materials for specific applications.