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 app...

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Main Authors:	Lucio Melone, Manuel Petroselli, Nadia Pastori, Carlo Punta
Format:	Article
Language:	English
Published:	MDPI AG 2015-08-01
Series:	Molecules
Subjects:	N-hydroxyphthalimide cyclodextrin polyunsaturated fatty acids lipid peroxidation reactive oxygen species oxidative stress cancer
Online Access:	http://www.mdpi.com/1420-3049/20/9/15881

id	doaj-efcaef90a1854386960080748a4e07c2
record_format	Article
spelling	doaj-efcaef90a1854386960080748a4e07c22020-11-24T23:15:34ZengMDPI AGMolecules1420-30492015-08-01209158811589210.3390/molecules200915881molecules200915881Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant OrganocatalystsLucio Melone0Manuel Petroselli1Nadia Pastori2Carlo Punta3Department of Chemistry, Materials, and Chemical Engineering "G. Natta"—Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, ItalyDepartment of Chemistry, Materials, and Chemical Engineering "G. Natta"—Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, ItalyDepartment of Chemistry, Materials, and Chemical Engineering "G. Natta"—Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, ItalyDepartment of Chemistry, Materials, and Chemical Engineering "G. Natta"—Politecnico di Milano, Piazza Leonardo da Vinci 32, Milano I-20133, ItalyN-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.http://www.mdpi.com/1420-3049/20/9/15881N-hydroxyphthalimidecyclodextrinpolyunsaturated fatty acidslipid peroxidationreactive oxygen speciesoxidative stresscancer
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Lucio Melone Manuel Petroselli Nadia Pastori Carlo Punta
spellingShingle	Lucio Melone Manuel Petroselli Nadia Pastori Carlo Punta Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts Molecules N-hydroxyphthalimide cyclodextrin polyunsaturated fatty acids lipid peroxidation reactive oxygen species oxidative stress cancer
author_facet	Lucio Melone Manuel Petroselli Nadia Pastori Carlo Punta
author_sort	Lucio Melone
title	Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts
title_short	Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts
title_full	Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts
title_fullStr	Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts
title_full_unstemmed	Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts
title_sort	functionalization of cyclodextrins with n-hydroxyphthalimide moiety: a new class of supramolecular pro-oxidant organocatalysts
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2015-08-01
description	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.
topic	N-hydroxyphthalimide cyclodextrin polyunsaturated fatty acids lipid peroxidation reactive oxygen species oxidative stress cancer
url	http://www.mdpi.com/1420-3049/20/9/15881
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Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts

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