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Bisphosphonate‐functionalized poly(β‐amino ester) network polymers
Author(s) -
Guven Melek Naz,
Seckin Altuncu Merve,
Demir Duman Fatma,
Eren Tugce Nur,
Yagci Acar Havva,
Avci Duygu
Publication year - 2017
Publication title -
journal of biomedical materials research part a
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.849
H-Index - 150
eISSN - 1552-4965
pISSN - 1549-3296
DOI - 10.1002/jbm.a.36026
Subject(s) - materials science , methacrylate , ethylene glycol , polymer , self healing hydrogels , degradation (telecommunications) , bisphosphonate , polymer chemistry , biodegradation , amine gas treating , organic chemistry , copolymer , chemistry , composite material , medicine , telecommunications , osteoporosis , computer science , endocrinology
Three novel bisphosphonate‐functionalized secondary diamines are synthesized and incorporated into poly(β‐amino ester)s (PBAEs) to investigate the effects of bisphosphonates on biodegradation and toxicity of PBAE polymer networks. These three novel amines, BPA1, BPA2, and BPA3, were prepared from the reactions of 1,4‐butanediamine, 1,6‐hexanediamine, or 4,9‐dioxa‐1,12‐dodecanediamine with tetraethyl vinylidene bisphosphonate, respectively. The PBAE macromers were obtained from the aza‐Michael addition reaction of these amines to 1,6‐hexane diol diacrylate (HDDA) and poly(ethylene glycol) diacrylate (PEGDA, M n = 575) and photopolymerized to produce biodegradable gels. These gels with different chemistries exhibited similar degradation behavior with mass loss of 53–73% within 24 h, indicating that degradation is mostly governed by the bisphosphonate group. Based on the in vitro cytotoxicity evaluation against NIH 3T3 mouse embryonic fibroblast cells, the degradation products do not exhibit significant toxicity in most cases. It was also shown that PBAE macromers can be used as cross‐linkers for the synthesis of 2‐hydroxyethyl methacrylate hydrogels, conferring small and customizable degradation rates upon them. The materials reported have potential to be used as nontoxic degradable biomaterials. © 2017 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 105A: 1412–1421, 2017.