Bisphosphonate-functionalized poly(β-amino ester) network polymers.
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, Mn= 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.
Department of Chemistry, Bogazici University, 34342 Bebek, Istanbul, Turkey.
Melek Naz
MN
Guven
Department of Chemistry, Bogazici University, 34342 Bebek, Istanbul, Turkey.
Merve
M
Seckin Altuncu
Graduate School of Materials Science and Engineering, Koc University, Sariyer, Istanbul, 34450, Turkey.
Fatma
F
Demir Duman
Department of Chemistry, Bogazici University, 34342 Bebek, Istanbul, Turkey.
Tugce Nur
TN
Eren
Graduate School of Materials Science and Engineering, Koc University, Sariyer, Istanbul, 34450, Turkey.|Department of Chemistry, Koc University, Sariyer, Istanbul, 34450, Turkey.
Havva
H
Yagci Acar
Department of Chemistry, Bogazici University, 34342 Bebek, Istanbul, Turkey.
Duygu
D
Avci
D000818:Animals; D063566:Biodegradable Plastics / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D004164:Diphosphonates / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D005347:Fibroblasts / Q000166:cytology / Q000378:metabolism*; D008422:Materials Testing; D051379:Mice; D041681:NIH 3T3 Cells; D011108:Polymers / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology
D063566:Biodegradable Plastics; D004164:Diphosphonates; D011108:Polymers; C507253:poly(beta-amino ester)
biocompatibility; biodegradable polymer; cross-linked polymers; cytotoxicity; poly(β-aminoester)