title: Joining Two Natural Motifs: Catechol-Containing Poly(phosphoester)s.
abstract: Numerous catechol-containing polymers, including biodegradable polymers, are currently heavily discussed for modern biomaterials. However, there is no report combining poly(phosphoester)s (PPEs) with catechols. Adhesive PPEs have been prepared via acyclic diene metathesis polymerization. A novel acetal-protected catechol phosphate monomer was homo- and copolymerized with phosphoester comonomers with molecular weights up to 42000 g/mol. Quantitative release of the catechols was achieved by careful hydrolysis of the acetal groups without backbone degradation. Degradation of the PPEs under basic conditions revealed complete and statistical degradation of the phosphotri- to phosphodiesters. In addition, a phosphodiester monomer with an adhesive P-OH group and no protective group chemistry was used to compare the binding to metal oxides with the multicatechol-PPEs. All PPEs can stabilize magnetite particles (NPs) in polar solvents, for example, methanol, due to the binding of the phosphoester groups in the backbone to the particles. ITC measurements reveal that multicatechol PPEs exhibit a higher binding affinity to magnetite NPs compared to PPEs bearing phosphodi- or phosphotriesters as repeating units. In addition, the catechol-containing PPEs were used to generate organo- and hydrogels by oxidative cross-linking, due to cohesive properties of catechol groups. This unique combination of two natural adhesive motives, catechols and phosphates, will allow the design of novel future gels for tissue engineering applications or novel degradable adhesives.
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.|Graduate School Materials Science in Mainz, Staudinger Weg 9, 55128 Mainz, Germany.
authors.forename: Greta
authors.initials: G
authors.lastname: Becker
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
authors.forename: Lisa-Maria
authors.initials: LM
authors.lastname: Ackermann
authors.affiliation: Johannes Gutenberg-University Mainz , Institute of Inorganic Chemistry and Analytical Chemistry, Duesbergweg 10-14, 55128 Mainz, Germany.|Graduate School Materials Science in Mainz, Staudinger Weg 9, 55128 Mainz, Germany.
authors.forename: Eugen
authors.initials: E
authors.lastname: Schechtel
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Klapper
authors.affiliation: Johannes Gutenberg-University Mainz , Institute of Inorganic Chemistry and Analytical Chemistry, Duesbergweg 10-14, 55128 Mainz, Germany.
authors.forename: Wolfgang
authors.identifier: 0000-0002-4536-994X
authors.initials: W
authors.lastname: Tremel
authors.affiliation: Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.
authors.forename: Frederik R
authors.identifier: 0000-0002-6955-8489
authors.initials: FR
authors.lastname: Wurm
mesh_terms: D001672:Biocompatible Materials / Q000737:chemistry; D002396:Catechols / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry; D005782:Gels / Q000737:chemistry; D006868:Hydrolysis; D053758:Nanoparticles / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry*; D058105:Polymerization; D011108:Polymers / Q000737:chemistry*; D023822:Tissue Engineering
chemical_list: D001672:Biocompatible Materials; D002396:Catechols; D004952:Esters; D005290:Ferric Compounds; D005782:Gels; D010710:Phosphates; D011108:Polymers; C000499:ferric oxide