Hydrazone-based hydrogel hydrolytically degradable in acidic environment

We describe the synthesis of new crosslinker N′-{3-[2-(4-{2-[3-(methacryloylamino)propanoyl]hydrazono}cyclohexyliden)hydrazino]-3-oxopropyl}-2-methylacrylamide, which is stable at physiological pH, but is hydrolytically cleaved in acidic pH. Study of acid hydrolysis showed that the crosslinker is hydrolyzed into two N′-(3-hydrazino-3-oxopropyl)-2-methylacrylamide molecules and one 1,4-cyclohexanedione molecule. Hydrogels based on poly[N-(2-hydroxypropyl)methacrylamide] crosslinked with this crosslinker were prepared and their degradation rate was studied as a function of pH (in the range of pH 1.5-7.4). The hydrogel is cleaved within 8-27 days at pH between 1.5 and 6 and is stable at pH 7.4 making it promising for the construction of oesophageal stents.