Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts.
N-hydroxyphthalimide (NHPI) is an organocatalyst for free-radical processes able to promote the aerobic oxidation of a wide range of organic substrates. In particular, NHPI can catalyze the hydroperoxidation of polyunsaturated fatty acids (PUFA). This property could be of interest for biological applications. This work reports the synthesis of two β-cyclodextrin derivatives (CD5 and CD6) having a different degree of methylation and bearing a NHPI moiety. These compounds, having different solubility in water, have been successfully tested for the hydroperoxidation of methyl linoleate, chosen as the PUFA model molecule.
Department of Chemistry, Materials, and Chemical Engineering "G. Natta"-Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, Italy. lucio.melone@polimi.it.|INSTM, National Consortium of Materials Science and Technology, Local Unit Politecnico di Milano, Milano 20133, Italy. lucio.melone@polimi.it.|Università Telematica e-Campus, Via Isimbardi 10, Novedrate 22060, Italy. lucio.melone@polimi.it.
Lucio
L
Melone
Department of Chemistry, Materials, and Chemical Engineering "G. Natta"-Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, Italy. manuel.petroselli@polimi.it.|INSTM, National Consortium of Materials Science and Technology, Local Unit Politecnico di Milano, Milano 20133, Italy. manuel.petroselli@polimi.it.
Manuel
M
Petroselli
Department of Chemistry, Materials, and Chemical Engineering "G. Natta"-Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, Italy. nadia.pastori@polimi.it.|INSTM, National Consortium of Materials Science and Technology, Local Unit Politecnico di Milano, Milano 20133, Italy. nadia.pastori@polimi.it.
Nadia
N
Pastori
Department of Chemistry, Materials, and Chemical Engineering "G. Natta"-Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, Italy. carlo.punta@polimi.it.|INSTM, National Consortium of Materials Science and Technology, Local Unit Politecnico di Milano, Milano 20133, Italy. carlo.punta@polimi.it.
Carlo
C
Punta
D003505:Cyclodextrins / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D015227:Lipid Peroxidation; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D010797:Phthalimides / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000737:chemistry
D003505:Cyclodextrins; D005231:Fatty Acids, Unsaturated; D010797:Phthalimides; D017382:Reactive Oxygen Species; C037437:N-hydroxyphthalimide
N-hydroxyphthalimide; cancer; cyclodextrin; lipid peroxidation; oxidative stress; polyunsaturated fatty acids; reactive oxygen species