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Towards potential nanoparticle contrast agents: Synthesis of new functionalized PEG bisphosphonates

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ABSTRACT

The use of nanotechnologies for biomedical applications took a real development during these last years. To allow an effective targeting for biomedical imaging applications, the adsorption of plasmatic proteins on the surface of nanoparticles must be prevented to reduce the hepatic capture and increase the plasmatic time life. In biologic media, metal oxide nanoparticles are not stable and must be coated by biocompatible organic ligands. The use of phosphonate ligands to modify the nanoparticle surface drew a lot of attention in the last years for the design of highly functional hybrid materials. Here, we report a methodology to synthesize bisphosphonates having functionalized PEG side chains with different lengths. The key step is a procedure developed in our laboratory to introduce the bisphosphonate from acyl chloride and tris(trimethylsilyl)phosphite in one step.

No MeSH data available.


Synthesis of PEG-HMBPs 1 and 1’.
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C3: Synthesis of PEG-HMBPs 1 and 1’.

Mentions: Starting materials, the free alcohol PEG and monomethyl ether PEGs (compounds 3a,b) with various chain lengths (n = 4, 7 and 12) were commercially available. Firstly, the free alcohol PEG was selectively monoprotected with a benzyl group (Scheme 3).


Towards potential nanoparticle contrast agents: Synthesis of new functionalized PEG bisphosphonates
Synthesis of PEG-HMBPs 1 and 1’.
© Copyright Policy - Beilstein
Related In: Results  -  Collection

License 1 - License 2
Show All Figures
getmorefigures.php?uid=PMC4979661&req=5

C3: Synthesis of PEG-HMBPs 1 and 1’.
Mentions: Starting materials, the free alcohol PEG and monomethyl ether PEGs (compounds 3a,b) with various chain lengths (n = 4, 7 and 12) were commercially available. Firstly, the free alcohol PEG was selectively monoprotected with a benzyl group (Scheme 3).

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The use of nanotechnologies for biomedical applications took a real development during these last years. To allow an effective targeting for biomedical imaging applications, the adsorption of plasmatic proteins on the surface of nanoparticles must be prevented to reduce the hepatic capture and increase the plasmatic time life. In biologic media, metal oxide nanoparticles are not stable and must be coated by biocompatible organic ligands. The use of phosphonate ligands to modify the nanoparticle surface drew a lot of attention in the last years for the design of highly functional hybrid materials. Here, we report a methodology to synthesize bisphosphonates having functionalized PEG side chains with different lengths. The key step is a procedure developed in our laboratory to introduce the bisphosphonate from acyl chloride and tris(trimethylsilyl)phosphite in one step.

No MeSH data available.