Synthesis of Sugar-Polysiloxane Hybrids Having Rigid Main-Chains and Formation of their Nano Aggregates

Abstract

ABSTRACT:We synthesized sugar-polysiloxane hybrids having rigid main-chains by reaction of sugar-lactones with amine-functionalized polysiloxane (1). Reaction of gluconolactone (2) with 1 was performed to obtain polysiloxane (3) having polyol moieties derived from glucose. This material has the regularly controlled higher-ordered structure in solid state such as the hexagonal phase. A hydrophilic sugar-polysiloxane hybrid (5) was prepared by reaction of lactobionolactone (4) with 1. Furthermore, an amphiphilic sugar-polysiloxane hybrid (8) was synthesized by introduction of stearoyl groups in addition to sugar groups on the surface of 1. The SEM image of the amphiphilic material 8 exhibited formation of nano aggregates having the particle diameters of ca. 50 nm in water.[doi:10.1295/polymj.PJ2006268] KEY WORDS Glycopolymer / Sugar-lactone / Polysiloxane / Amphiphilic / Hybrid / Nano Aggregate / There has been a growing interest in sugar portions of the glycoproteins because of exhibiting to bind to carbohydrate-recognition proteins, toxins, viruses, and cells. It has been known that a molecular assembly formed from the sugar-residues in the living system expresses stronger recognition ability than that of a single sugar molecule. This, so-called multivalent or cluster effect, has become a principle in the design of artificial glycoconjugate ligands. Therefore, polymeric materials having such functional sugar-residues, i.e., 'glycopolymer', have widely been investigated because these materials efficiently show the multivalent effect.

Nitric Oxide Release in Human Aortic Endothelial Cells Mediated by Delivery of Amphiphilic Polysiloxane Nanoparticles to Caveolae

“…Amphiphilic polysiloxane (Am-PAPS) was prepared by the method described in our previous report. 15 Am-PAPS was labeled with fluorescein thioisocyanate and was named Flu-Am-PAPS. Rabbit anti-caveolin-1 IgG was purchased from Sigma (St. Louis, MI).…”

Direct Synthesis of Peptide‐Containing Silicones: A New Way to Bioactive Materials

“…Moreover, the highly hydrophobic surface of PDMS leads to unselective adsorption and subsequent denaturation of proteins . Simple chemical modifications (e.g., alkyl chains, cationic and anionic groups) of the hydrophobic native PDMS surface have been used to improve its biocompatibility, and more complex molecules such as sugars, poly( l ‐lactic acid), as well as peptides and proteins have been immobilized on PDMS to impart chosen bioactivities to the material. These modifications were performed by multistep grafting chemistry, in which a functional group is attached to the PDMS surface and then reacts with the molecule to be immobilized.…”

Turning peptides in comb silicone polymers

“…Despite their outstanding properties such as resistance to temperature and chemicals, high flexibility and elasticity, there is still a need for functional silicones whose properties can be adjusted by the addition of a bioorganic moiety. Sugar‐silicon or poly( l ‐lactic acid)‐silicon hybrids have been reported for cell recognition and bone tissue regeneration . The association of silicone and peptides has also been proposed for improved cell–material interactions or detection purposes, but it has been mostly limited to functionalize silicone surface with short peptides .…”