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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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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/78891</identifier>
  <creators>
    <creator>
      <creatorName>Bingol, H. Betul</creatorName>
      <givenName>H. Betul</givenName>
      <familyName>Bingol</familyName>
      <affiliation>Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Altin, Ayse</creatorName>
      <givenName>Ayse</givenName>
      <familyName>Altin</familyName>
      <affiliation>Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Bal, Tugba</creatorName>
      <givenName>Tugba</givenName>
      <familyName>Bal</familyName>
      <affiliation>Koc Univ, Dept Chem &amp; Biol Engn, TR-34450 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Agopcan-Cinar, Sesil</creatorName>
      <givenName>Sesil</givenName>
      <familyName>Agopcan-Cinar</familyName>
      <affiliation>Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Kizilel, Seda</creatorName>
      <givenName>Seda</givenName>
      <familyName>Kizilel</familyName>
      <affiliation>Koc Univ, Dept Chem &amp; Biol Engn, TR-34450 Istanbul, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Avci, Duygu</creatorName>
      <givenName>Duygu</givenName>
      <familyName>Avci</familyName>
      <affiliation>Bogazici Univ, Dept Chem, TR-34342 Istanbul, Turkey</affiliation>
    </creator>
  </creators>
  <titles>
    <title>Synthesis And Evaluation Of New Phosphonic Acid-Functionalized Acrylamides With Potential Biomedical Applications</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2015</publicationYear>
  <dates>
    <date dateType="Issued">2015-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/78891</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1002/pola.27746</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">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.</description>
  </descriptions>
</resource>
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