Optimisation of alendronate conjugation to polyethylene glycol for functionalisation of biopolymers and nanoparticles
| Autor: | Asim Mushtaq, A. Anitha, Hamish Poli, Craig A. Bell, Ross P. McGeary, Lisbeth Grøndahl |
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| Rok vydání: | 2021 |
| Předmět: |
Polymers and Plastics
Organic Chemistry technology industry and agriculture General Physics and Astronomy macromolecular substances Polyethylene glycol engineering.material Combinatorial chemistry Chitosan chemistry.chemical_compound chemistry Reagent PEG ratio Materials Chemistry Michael reaction engineering Amine gas treating Biopolymer Maleimide |
| Zdroj: | European Polymer Journal. 155:110571 |
| ISSN: | 0014-3057 |
| Popis: | The coupling of alendronate (ALN) to heterobifunctional polyethylene glycol (PEG) requires an orthogonal synthetic route. This can be achieved using thiolation of alendronate with 2-iminothiolane and subsequent Michael addition to maleimide functionalised PEG. This paper evaluates the chemical reactions between 2-iminothiolane and alendronate and demonstrates how reaction conditions previously reported for thiolation of amines are not ideal in reactions where the amine has a high pKa value, such as for amine-containing bisphosphonates. Furthermore, the optimised method for thiolation of alendronate is applied to the synthesis of alendronate functionalized PEGs, ALN-PEG-NH2 and ALN-PEG-COOH, with isolation and full characterization of these two products. Further conjugation of the latter onto the biopolymer chitosan is demonstrated, including evaluating reagent ratios on the degree of substitution. |
| Databáze: | OpenAIRE |
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