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Chemistry. 2017 Jul 18;23(40):9462-9466. doi: 10.1002/chem.201700782. Epub 2017 Jun 29.

Secondary-Rim γ-Cyclodextrin Functionalization to Conjugate with C60 : Improved Efficacy as a Photosensitizer.

Author information

1
Sorbonne Universités, UPMC Univ Paris 06, CNRS, Insititut Parisien de Chimie Moléculaire (UMR 8232), 4 Place Jussieu, 75005, Paris, France.
2
CEA Saclay, Service de Bioénergétique Biologie Structurale et Mécanismes, 91191, Gif-sur-Yvette, France.
3
Muséum National d'Histoire Naturelle, CNRS, Molécules de Communication et Adaptation des Microorganismes (UMR 7245), 63 Rue Buffon, 75005, Paris, France.
4
Jianghan University, Institute for Interdisciplinary Research, 430056, Wuhan, P. R. China.

Abstract

DIBAL-H-mediated demethylation provides a novel method to access secondary-rim functionalized γ-cyclodextrin. 2A ,3B -Dihydroxyl-per-O-methylated-γ-cyclodextrin has been obtained, whose conjugation with C60 allows access to the most water-soluble C60 conjugate described so far. The water solubility of 0.12 m (550 mg mL-1 ) is 150 times higher than that of the native γ-CD/C60 complex. Its singlet oxygen (1 O2 ) quantum yield is 0.39, an increase of one to two orders of magnitude compared to that of α(β)CD-C60 conjugates.

KEYWORDS:

C60; aggregation; gamma-CD; photosensitizer; secondary rim

PMID:
28548683
DOI:
10.1002/chem.201700782

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