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

Xiaolei Zhu; Annamaria Quaranta; René V Bensasson; Matthieu Sollogoub; Yongmin Zhang

doi:10.1002/chem.201700782

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

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

Authors

Xiaolei Zhu¹, Annamaria Quaranta², René V Bensasson³, Matthieu Sollogoub¹, Yongmin Zhang^{1

4}

Affiliations

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.

PMID: 28548683
DOI: 10.1002/chem.201700782

Abstract

DIBAL-H-mediated demethylation provides a novel method to access secondary-rim functionalized γ-cyclodextrin. 2^A ,3^B -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.