Hydrazone-based hydrogel hydrolytically degradable in acidic environment

0359454 - ÚMCH 2012 RIV NL eng J - Článek v odborném periodiku
Vetrík, Miroslav - Přádný, Martin - Hrubý, Martin - Michálek, Jiří
Hydrazone-based hydrogel hydrolytically degradable in acidic environment.
Polymer Degradation and Stability. Roč. 96, č. 5 (2011), s. 756-759. ISSN 0141-3910. E-ISSN 1873-2321
Grant CEP: GA ČR GAP108/10/1560; GA ČR GPP207/10/P054; GA MŠMT 1M0538
Výzkumný záměr: CEZ:AV0Z40500505
Klíčová slova: polymer * hydrogel * hydrazone bond
Kód oboru RIV: CD - Makromolekulární chemie
Impakt faktor: 2.769, rok: 2011

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.
Trvalý link: http://hdl.handle.net/11104/0197240