Synthesis and evaluations of bisphosphonate‐containing monomers for dental materials

Akgun, Burcin; Avcı, Duygu

doi:10.1002/pola.26305

Cited by 16 publications

(17 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The polymer–drug conjugates with bisphosphonic acid groups are expected to both improve efficiency of drugs and reduce side effects by increasing the solubility of drugs and its blood‐circulation time. Examples of bisphosphonates in biomedical uses include bisphosphonate‐modified polyurethanes to resist calcification around implants, hyaluronic acid/BP hydrogels, and self‐etching dental adhesives containing bisphosphonates …”

Section: Introductionmentioning

confidence: 99%

Bisphosphonate‐functionalized poly(β‐amino ester) network polymers

Guven

Altuncu

Duman

et al. 2017

J Biomedical Materials Res

Self Cite

View full text Add to dashboard Cite

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 = 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.

show abstract

Section: Introductionmentioning

confidence: 99%

Bisphosphonate‐functionalized poly(β‐amino ester) network polymers

Guven

Altuncu

Duman

et al. 2017

J Biomedical Materials Res

Self Cite

View full text Add to dashboard Cite

show abstract

“…As mentioned, most of the published works in this field relate to phosphates or phosphonate groups while research on bisphosphonic monomers or polymers is very rare. Recently, Avci et al described the design and synthesis of a bisphosphonic moiety based on methacrylamide or bismethacrylamide monomers and its copolymerization with 2‐hydroxyethyl methacrylate 14…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of hydroxy‐bisphosphonate micrometer‐sized particles by dispersion polymerization of a new styrylbisphosphonate monomer

Chen

Goldshtein

Margel

2013

J. Polym. Sci. A Polym. Chem.

View full text Add to dashboard Cite

Bisphosphonates (BPs) are nonhydrolyzable pyrophosphate (P‐O‐P) analogs possessing two phosphonate groups linked to a single carbon (P‐C‐P). The hydroxy‐bisphosphonates (hydroxyBPs) are obtained when the hydroxy group is also linked to this bridging carbon. Their ability to form bidentate or tridentate chelates with calcium ions results in a high affinity to hydroxyapatite (HAP) in dentin, enamel and bones. In this study, we designed and prepared crosslinked poly(styrylbisphosphonate) (PStBP) micrometer‐sized particles by dispersion polymerization of the styrylbisphosphonate (StBP) and ethylene glycol dimethacrylate (EDMA) monomers. The new StBP monomer was synthesized in an efficient one‐pot synthesis using tris(trimethylsilyl)phosphite as the phosphorus source followed by methanolysis. The StBP monomer was successfully isolated and characterized as tri‐sodium salt. Polymerization of the StBP monomer was carried out in two steps: in situ conversion of the tri‐sodium StBP monomer back to its acid form, followed by radical dispersion polymerization in the presence of the crosslinker EDMA monomer. The resulting crosslinked PStBP micrometer‐sized particles retained the unique high affinity of the hydroxy‐bisphosphonate side groups to calcium ions and exhibited good adhesive properties to HAP. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

show abstract

“…23, and they were shown to be viable materials for tissue regeneration and other biomedical applications. [41][42][43][44][45][46][47][48] Mineralization of polymeric hydrogel scaffolds, with the aim of mimicking bone structure for tissue engineering applications, is another interesting field in which phosphorus containing moieties can be used. 24,25 Electrospun fibrous scaffolds 26,27 and thermosets based on a dual curing process 28 are reported.…”

Section: Introductionmentioning

confidence: 99%

Phosphonate‐functionalized poly(β‐amino ester) macromers as potential biomaterials

Akyol

Tatliyuz

Duman

et al. 2018

J Biomedical Materials Res

Self Cite

View full text Add to dashboard Cite

Biodegradability, hemocompatibility, resistance to protein adsorption, and strong interactions with hydroxyapatite (HAP)-based tissues such as dentin, enamel, and bone are important properties of phosphorus-containing biomaterials. Here, novel phosphonate-functionalized poly(β-amino ester) (PBAE) macromers are synthesized through aza-Michael addition of various diacrylates [1,6-hexanediol diacrylate (HDDA), poly(ethylene glycol) diacrylate (PEGDA, M = 575), 1,4-butanediol diacrylate (BDDA), 1,6-hexanediol ethoxylate diacrylate (HDEDA) and triethylene glycol diacrylate (TEGDA)] and a phosphonate-containing primary amine (diethyl 2-aminoethylphosphonate, A1) efficiently without any catalyst; where replacement of A1 with propyl amine (PA) served as control. The macromers, whose molecular weight is ca. 1000-4000 Da as confirmed by both GPC and H-NMR spectroscopy, are photopolymerized to give biodegradable gels. The degradation behavior and cell interaction of these gels are studied. The degradation rates of the gels can be varied by choice of starting acrylates and the acrylate:amine ratio. Furthermore, the gels showed slightly higher degradability than PA-based analogs (controls). Except TEGDA and PEGDA-based ones, all phosphonate-functionalized PBAE gels supported the attachment of larger number of SaOS-2 cells than nonphosphonated ones and the best film was found to be the one based on HDEDA-A1 with balanced hydrophilicity. Degradation products of these films have no significant cytotoxicity except HDDA-PA. © 2018 Wiley Periodicals, Inc. J Biomed Mater Res Part A: 106A: 1390-1399, 2018.

show abstract

Synthesis and evaluations of bisphosphonate‐containing monomers for dental materials

Cited by 16 publications

References 28 publications

Bisphosphonate‐functionalized poly(β‐amino ester) network polymers

Bisphosphonate‐functionalized poly(β‐amino ester) network polymers

Synthesis and characterization of hydroxy‐bisphosphonate micrometer‐sized particles by dispersion polymerization of a new styrylbisphosphonate monomer

Phosphonate‐functionalized poly(β‐amino ester) macromers as potential biomaterials

Contact Info

Product

Resources

About