Oligosaccharide‐Modified Poly(propyleneimine) Dendrimers: Synthesis, Structure Determination, and Cu^II Complexation

Abstract

The multiple application of reductive amination on primary amino groups of first and second generation poly(propyleneimine) dendrimers is used as a one-pot approach to introduce twice the amount of the oligosaccharide units as surface groups, compared to initially present amino groups in the first and second generation dendrimers. This was proven by (1)H NMR, MALDI-TOF-MS, and LILBID-MS analysis. The size of these dendrimers was determined by the hydrodynamic radius using pulsed field gradient NMR and dynamic light scattering. Molecular modeling confirmed the presence of dense-shell dendrimers. These dendrimers exhibit a generation dependent Cu(II)/dendrimer ratio in an aqueous environment, highlighting these materials as possible metal-carrier systems with a well-defined oligosaccharide protection shell for application in a biological environment.

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

“…Long alkyl spacer to give flexibility (Han, et al, 2007b) Poly-(propyleneimine) Maltose and maltotriose TOF (DHB) Synthesis, Structure determination and Cu(II) complexation (Appelhans, et al, 2007) Porphyrin Glucose TOF…”

Dense-shell glycodendrimers: UV/Vis and electron paramagnetic resonance study of metal ion complexation

“…We used UV/Vis titration and EPR experiments to intensively study the Cu(II) complexation behaviour of a series of PPI dendrimers ranging up to the fifth generation that had either a dense maltose (Klajnert et al 2008) or maltotriose shell (first and second generations in Appelhans et al (2007). All glycodendrimers are characterized by an extended dendritic tertiary amino group scaffold surrounded by a dense oligosaccharide shell for metal ion complexation.…”

“…Maltotriose-modified second-generation PPI (5) was synthesized according to the literature (Appelhans et al 2007). …”

“…Kodama & Fujisawa 2008). Owing to their well-defined oligosaccharide protection, dense-shell dendrimers may fulfil these criteria for use as metal ion carriers for biological applications (Appelhans et al 2007).…”

Design of Artificial Selenoenzymes Based on Macromolecular Scaffolds

“…The three‐dimensional topology structures of dendrimer and hyperbranched polymers are attracting great interest for their applications in chemistry and biology 61–63. Recently, by taking advantage of the microenviroment provided by the dendrimers and also by introducing catalytic groups (selenium/tellurium) into the core of dendrimers, some GPx mimics with high GPx activity have been successfully achieved.…”