Tricarbonyl-rhenium complexes of a thiol-functionalized amphoteric poly(amidoamine)

Daniela Donghi, Daniela Maggioni, Giuseppe D'Alfonso, Federica Amigoni, Elisabetta Ranucci, Paolo Ferruti, Amedea Manfredi, Fabio Fenili, Agnese Bisazza, Roberta Cavalli

Research output: Contribution to journalArticle

Abstract

An amphoteric thiol-functionalized poly(amidoamine) nicknamed ISA23SH10% was synthesized. Rhenium complexes 1 and 2, containing 0.5 and 0.8 equiv of rhenium, respectively, were easily obtained by reacting ISA23SH10% with [Re(CO)3(H2O)3](CF3SO 3) in aqueous solution at pH 5.5. Both ISA23SH10%, and its rhenium complexes were soluble in water under physiological conditions. The resultant solutions were stable, even in the presence of cysteine. Rhenium chelation occurred through the S and N atoms of the cysteamine moiety, as demonstrated by 1H, 13C, and 15N NMR spectroscopy. The diffusion coefficients and the hydrodynamic radii of ISA23SH10% and complex 1 were determined by pulsed gradient spin echo (PGSE) NMR experiments. The radius of the rhenium complexes 1 and 2 was always slightly larger than that of the parent polymer. TEM analysis showed that both complexes form spherical nanoparticles with narrow size distributions. Consistent results were obtained by dynamic light scattering. The observed sizes were in good agreement with those evaluated by PGSE. Preliminary in vitro and in vivo biological studies have been performed on complexes 1 and 2 as well as on the parent ISA23SH10%. Neither hemolytic activity of the two rhenium complexes and the parent polymer, up to a concentration of 5 mg/mL, nor cytotoxic effects were observed on Hela cell after 48 h at a concentration of 100 ng/mL. In vivo toxicological tests showed that ISA23SH10% is highly biocompatible, with a maximum tolerated dose (MTD) of 500 mg/kg. No toxic side effects were apparent after the intravenous injection in mice of the two rhenium complexes in doses up to 20 mg/kg.

Original languageEnglish
Pages (from-to)3273-3282
Number of pages10
JournalBiomacromolecules
Volume10
Issue number12
DOIs
Publication statusPublished - Dec 14 2009

ASJC Scopus subject areas

  • Bioengineering
  • Materials Chemistry
  • Polymers and Plastics
  • Biomaterials

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    Donghi, D., Maggioni, D., D'Alfonso, G., Amigoni, F., Ranucci, E., Ferruti, P., Manfredi, A., Fenili, F., Bisazza, A., & Cavalli, R. (2009). Tricarbonyl-rhenium complexes of a thiol-functionalized amphoteric poly(amidoamine). Biomacromolecules, 10(12), 3273-3282. https://doi.org/10.1021/bm9008638