Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 31, Pages 12684-12688Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202001355
Keywords
antioxidants; air-water interface; calixarenes; host-guest complexes; mass spectrometry
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Funding
- National Key R&D Program of China [2018YFE0115000]
- NSF of Tianjin City [19JCYBJC19600]
- Beckman Institute at Caltech
- NSF [CHE-1508825]
- NSFC [51873090, 21672112]
- Fundamental Research Funds for the Central Universities
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The oxidation of antioxidants by oxidizers imposes great challenges to both living organisms and the food industry. Here we show that the host-guest complexation of the carefully designed, positively charged, amphiphilic guanidinocalix[5]arene pentadodecyl ether (GC5A-12C) and negatively charged oleic acid (OA), a well-known cell membrane antioxidant, prevents the oxidation of the complex monolayers at the air-water interface from two potent oxidizers hydroxyl radicals (OH) and singlet delta oxygen (SDO). OH is generated from the gas phase and attacks from the top of the monolayer, while SDO is generated inside the monolayer and attacks amphiphiles from a lateral direction. Field-induced droplet ionization mass spectrometry results have demonstrated that the host-guest complexation achieves steric shielding and prevents both types of oxidation as a result of the tight and sleeved in physical arrangement, rather than the chemical reactivity, of the complexes.
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