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Synthesis of biomedical, fluorescence‐labelled polyesterurethanes for the investigation of their degradation

1997; Wiley; Volume: 198; Issue: 9 Linguagem: Inglês

10.1002/macp.1997.021980903

1521-3935

Gianluca Ciardelli, Kazushige Kojima, Andreas Lendlein, Peter Neuenschwander, Ulrich W. Suter,

biodegradable polymer synthesis and properties

Abstract The synthesis and characterization of fluorescence‐labelled, phase segregating block polyesterurethanes based on the known biocompatible and degradable materials poly[( R )‐3‐hydroxybutyric acid] (PHB), poly(ϵ‐caprolactone) (PCL), and poly[(ϵ‐caprolactone)‐ co ‐glycolide] (PCL/PGA) is described. To introduce fluorescence labels in the amorphous domains of the polymers, phenacyl 10,11‐dihydroxyundecanoate (PDUA) was synthesized and copolymerized with a PHB diol, a PCL diol, and aliphatic diisocyanates. After cleavage of the protecting group (without degradation of the polymer backbone), the carboxyl group was reacted with a fluorescent amine (dansylcadaverine) in the presence of 4,6‐diphenylthieno[3,4‐ d ]‐1,3‐dioxol‐2‐one 5,5‐dioxide (Steglich reagent). Also a polymer containing 13 C‐labelled carboxy groups was synthesized and the labelling reaction monitored by 13 C NMR spectroscopy. To introduce fluorescence labels in the hard segment of the polymers, a new low‐molecular‐weight diol based on poly[( R )‐hydroxybutyric acid] and containing protected carboxy groups was synthesized. After the deprotection, the carboxy groups were reacted with a fluorescent amine (dansylcadaverine) in the presence of an activating system based on dicyclohexylcarbodiimide. The labelled PHB diol was then copolymerized with a poly[(ϵ‐caprolactone)‐ co ‐glycolide] diol and an aliphatic diisocyanate. The so obtained fluorescence‐labelled block polyesterurethanes are promissing materials for the investigation of the biocompatibility and degradation of the corresponding, non‐labelled materials (DegraPol®) by means of fluorescence‐aided microscopic and spectroscopic techniques.