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

Xiaolei Zhu (1) , Annamaria Quaranta (2) , René Bensasson (3) , Matthieu Sollogoub (4) , Yongmin Zhang (4)

1 IPCM - Institut Parisien de Chimie Moléculaire
2 CEA Saclay, Département de Biologie Cellulaire et Moléculaire, Section de Bioénergétique
3 MCAM - Molécules de Communication et Adaptation des Micro-organismes
4 GOBS - Glycochimie Organique Biologique et Supramoléculaire

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

Mots clés: gamma-CD * secondary rim * C60 * aggregation * photosensitizer; GOBS; POLE 3

Domaines: Chimie

Xiaolei Zhu, Annamaria Quaranta, René Bensasson, Matthieu Sollogoub, Yongmin Zhang. Secondary-Rim γ-Cyclodextrin Functionalization to Conjugate with C60: Improved Efficacy as Photosensitizer. Chemistry - A European Journal, 2017, pp.n/a-n/a. ⟨10.1002/chem.201700782⟩. ⟨hal-02891086⟩