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Synthesis and evaluation of new phosphonic acid-functionalized acrylamides with potential biomedical applications

Bingol, H. Betul; Altin, Ayse; Bal, Tugba; Agopcan-Cinar, Sesil; Kizilel, Seda; Avci, Duygu


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        "affiliation": "Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey", 
        "name": "Bingol, H. Betul"
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      {
        "affiliation": "Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey", 
        "name": "Altin, Ayse"
      }, 
      {
        "affiliation": "Koc Univ, Dept Chem & Biol Engn, TR-34450 Istanbul, Turkey", 
        "name": "Bal, Tugba"
      }, 
      {
        "affiliation": "Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey", 
        "name": "Agopcan-Cinar, Sesil"
      }, 
      {
        "affiliation": "Koc Univ, Dept Chem & Biol Engn, TR-34450 Istanbul, Turkey", 
        "name": "Kizilel, Seda"
      }, 
      {
        "affiliation": "Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey", 
        "name": "Avci, Duygu"
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    "description": "Phosphorus-containing acidic monomers are able to interact with the inorganic phase of mineralized tissues such as enamel, dentin, and bone. From this perspective, three phosphonic acid-containing acrylamide monomers with different lengths of alkyl chains were synthesized to be used for both self-etching dental adhesives and mineralized hydrogel scaffolds. Monomers were synthesized by the reaction of -aminophosphonates (diethyl aminomethylphosphonate, diethyl 2-aminobutan-2-ylphosphonate, and diethyl 2-aminooctan-2-ylphosphonate) with acryloyl chloride followed by the hydrolysis of phosphonate groups by using trimethylsilyl bromide. The properties such as pH in the range of mild self-etching adhesives, hydrolytic stability, high rate of copolymerizations with 2-hydroxyethyl methacrylate (HEMA) and HEMA/glycerol dimethacrylate, giving high-molecular-weight polymers on thermal polymerization, and strong decalcification ability of hydroxyapatite make these monomers good candidates for self-etching adhesives, although no appreciable effect of the number and size of the -substituents was observed. Hydrogel scaffolds containing phosphonic acid groups were fabricated, characterized, and mineralized. Altogether, the results suggest that these phosphonic acid-containing monomers have suitable properties to be used in fabrication of biomaterials for both dental and bone tissue engineering applications. (c) 2015 Wiley Periodicals, Inc.", 
    "doi": "10.1002/pola.27746", 
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      "issue": "23", 
      "pages": "2755-2767", 
      "title": "JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY", 
      "volume": "53"
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    "publication_date": "2015-01-01", 
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    "title": "Synthesis and evaluation of new phosphonic acid-functionalized acrylamides with potential biomedical applications"
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