Polymers from functional macrolactones as potential biomaterials: enzymatic ring opening polymerization, biodegradation, and biocompatibility.
We systematically investigated a series of polymers derived from macrolactones, namely, pentadecalactone, hexadecalactone, and their unsaturated analogues ambrettolide and globalide as potential biomaterials. By enzymatic ring-opening polymerization these monomers can conveniently be polymerized to high molecular weight. The polymers are highly crystalline with melting points around 95 degrees C for the saturated polymers and lower melting points for the unsaturated polymers (46-55 degrees C). All polymers are nontoxic as measured by an MTT assay for metabolic cell activity of a 3T3 mouse fibroblast cell line. Degradation studies showed no hydrolytic or enzymatic degradability of the polymers, which was ascribed to the high crystallinity and hydrophobicity of the materials. The unsaturated polymers were cross-linked in the melt, yielding fully amorphous transparent materials with a gel content of 97%.
van der Meulen
Inge
I
Laboratory of Polymer Chemistry, Eindhoven University of Technology, Den Dolech 2, Post Office Box 513, 5600 MB Eindhoven, The Netherlands.
de Geus
Matthijs
M
Antheunis
Harro
H
Deumens
Ronald
R
Joosten
Elbert A J
EA
Koning
Cor E
CE
Heise
Andreas
A
D016475:3T3 Cells; D000818:Animals; D001672:Biocompatible Materials / Q000009:adverse effects / Q000138:chemical synthesis* / Q000737:chemistry; D002470:Cell Survival / Q000187:drug effects; D004800:Enzymes, Immobilized; D005347:Fibroblasts / Q000187:drug effects / Q000378:metabolism; D005656:Fungal Proteins; D007783:Lactones / Q000737:chemistry*; D008049:Lipase / Q000737:chemistry*; D008422:Materials Testing; D051379:Mice; D015394:Molecular Structure; D008970:Molecular Weight; D011108:Polymers / Q000009:adverse effects / Q000138:chemical synthesis* / Q000737:chemistry; D044366:Transition Temperature
D001672:Biocompatible Materials; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D007783:Lactones; D011108:Polymers; C093667:Novozyme 435; D008049:Lipase