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Published on: October 15, 2019
Designer amphiphiles based on para-acyl-calix[8]arenes
Saïd Jebors1, Fabienne Fache, Sylvain Balme
1Institut de Biologie et Chimie des Protéines, 7 passage du Vercors, Lyon, F-69367, France.
New calix[8]arene derivatives with octanoyl or hexadecanoyl groups were synthesized. Certain anionic derivatives show anticoagulant properties without hemolytic toxicity, indicating potential therapeutic applications.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Medicinal Chemistry
Background:
- Calix[8]arenes are macrocyclic compounds with a unique structure.
- O-derivatization allows for tuning of calixarene properties.
- Para-acyl calix[8]arenes offer a platform for functionalization.
Purpose of the Study:
- To synthesize novel O-derivatised para-acyl-calix[8]arene compounds.
- To investigate the interfacial properties of these new derivatives.
- To evaluate the biological activity, specifically anticoagulant and hemolytic properties, of selected derivatives.
Main Methods:
- Multi-step organic synthesis for O-derivatisation.
- Interfacial property analysis using air-water interface techniques.
- Dynamic light scattering for studying protein interactions.
- Assessment of anticoagulant activity and hemolytic toxicity.
Main Results:
- Successful synthesis of fully O-derivatised para-octanoyl and para-hexadecanoyl calix[8]arenes in high yields.
- Formation of stable monolayers at the air-water interface for specific derivatives.
- Observed specific adsorption of O-4-sulfonatobutoxy-para-octanoylcalix[8]arene onto serum albumins.
- Anionic derivatives demonstrated anticoagulant properties with no observed hemolytic toxicity.
Conclusions:
- The synthesized calix[8]arene derivatives exhibit tunable interfacial properties.
- Anionic derivatives show promise as anticoagulants with a favorable safety profile.
- Further research into these compounds could lead to novel therapeutic agents.
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