Display options
Cite
Bowen RL, Carey CM, Flynn KM, et al. Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations. J Res Natl Inst Stand Technol. 2009;114(1):1-9doi: 10.6028/jres.114.001.
Bowen, R. L., Carey, C. M., Flynn, K. M., & Guttman, C. M. (2009). Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations. Journal of research of the National Institute of Standards and Technology, 114(1), 1-9. https://doi.org/10.6028/jres.114.001
Bowen, Rafael L, et al. "Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations." Journal of research of the National Institute of Standards and Technology vol. 114,1 (2009): 1-9. doi: https://doi.org/10.6028/jres.114.001
Bowen RL, Carey CM, Flynn KM, Guttman CM. Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations. J Res Natl Inst Stand Technol. 2009 Feb 01;114(1):1-9. doi: 10.6028/jres.114.001. Print 2009. PMID: 27504209; PMCID: PMC4651609.
Copy Download .nbib Format: NLM
Share it on

J Res Natl Inst Stand Technol. 2009 Feb 01;114(1):1-9. doi: 10.6028/jres.114.001. Print 2009.

Synthesis of Polymerizable Cyclodextrin Derivatives for Use in Adhesion-Promoting Monomer Formulations.

Journal of research of the National Institute of Standards and Technology

Rafael L Bowen, Clifton M Carey, Kathleen M Flynn, Charles M Guttman

Affiliations

  1. Paffenbarger Research Center, American Dental Association Foundation, Gaithersburg, MD 20899-8546.
  2. National Institute of Standards and Technology, Gaithersburg, MD 20899-0001.

PMID: 27504209 PMCID: PMC4651609 DOI: 10.6028/jres.114.001

Abstract

The synthesis of the cyclodextrin derivatives reported herein was assisted by extensive literature research together with structure-property relationships derived from three-dimensional molecular modeling. These studies led to the hypothesis that many of the 21 hydroxyl groups on beta-cyclodextrin molecules could be derivatized to form a closely related family of analogous chemical compounds containing both polymerizable groups and hydrophilic ionizable ligand (substrate-binding) groups, each attached via hydrolytically-stable ether-linkages. The vinylbenzylether polymerizable groups should readily homopolymerize and also copolymerize with methacrylates. This could be highly useful for dental applications because substantially all contemporary dental resins and composites are based on methacrylate monomers. Due to hydrophilic ligands and residual hydroxyl groups, these cyclodextrin derivatives should penetrate hydrated layers of dentin and enamel to interact with collagen and tooth mineral. Analyses indicated that the diverse reaction products resulting from the method of synthesis reported herein should comprise a family of copolymerizable molecules that collectively contain about 30 different combinations of vinylbenzyl and hexanoate groups on the various molecules, with up to approximately seven of such groups combined on some of the molecules. Although the hypothesis was supported, and adhesive bonding to dentin is expected to be significantly improved by the use of these polymerizable cyclodextrin derivatives, other efforts are planned for improved synthetic methods to ensure that each of the reaction-product molecules will contain at least one copolymerizable moiety. The long-term objective is to enable stronger and more durable attachments of densely cross-linked polymers to hydrated hydrophilic substrates. Capabilities for bonding of hydrolytically stable polymers to dental and perhaps other hydrous biological tissues could provide widespread benefits.

Keywords: MALDI-TOF-MS; beta-cyclodextrin; dental materials; monomer synthesis; polymerizable cyclodextrin derivatives

References

  1. J Dent Res. 1993 Mar;72 (3):582-6 - PubMed
  2. Dent Mater. 2005 Mar;21(3):210-6 - PubMed
  3. J Dent Res. 2000 Apr;79(4):905-11 - PubMed
  4. Structure. 1995 Sep 15;3(9):893-906 - PubMed
  5. J Dent Res. 2004 Jan;83(1):22-6 - PubMed
  6. Dent Mater. 2004 Jul;20(6):513-21 - PubMed
  7. J Esthet Dent. 1992 Jul-Aug;4(4):105-9 - PubMed
  8. Chem Rev. 1998 Jul 30;98(5):1743-1754 - PubMed
  9. J Am Chem Soc. 1974 Dec 25;96(26):8081-7 - PubMed
  10. Nat Rev Drug Discov. 2004 Dec;3(12):1023-35 - PubMed
  11. Biomaterials. 2005 Jun;26(18):3973-9 - PubMed
  12. J Res Natl Inst Stand Technol. 2009 Feb 01;114(1):11-20 - PubMed

Publication Types

Grant support