Starting from purpurin-18, a stable purpurin-18 imide derivative with intensive absorption in the near infrared has been synthesized. The opening of the exocycle anhydride by a primary alkylamine bearing an adamantyl group, allows after cyclization the formation of an imide function. This reaction l...

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Main Authors: Ndzimbou, Luce Janice, Chkair, Rayan, Ndong Ntoutoume, Gautier Mark Arthur, Diab-Assaf, Mona, Chemin, Guillaume, Liagre, Bertrand, Brégier, Frédérique, Sol, Vincent
Format: Article
Language:English
Published: Académie des sciences 2025-03-01
Series:Comptes Rendus. Chimie
Subjects:
Purpurinimide
Photosensitizers
Cellulose nanocrystals
Photodynamic therapy (PDT)
Colorectal cancer
Online Access:https://comptes-rendus.academie-sciences.fr/chimie/articles/10.5802/crchim.383/
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Summary:Starting from purpurin-18, a stable purpurin-18 imide derivative with intensive absorption in the near infrared has been synthesized. The opening of the exocycle anhydride by a primary alkylamine bearing an adamantyl group, allows after cyclization the formation of an imide function. This reaction led to the purpurinimide adamantane derivative (PIA) which enables the inclusion of a photosensitizer in the cavity of cationic cyclodextrin coupled to cellulose nanocrystals (CNCs/β-CD+). Preliminary in vitro results showed that CNCs/β-CD+ complexes improved internalization of photosensitizers into HCT116 and HT-29 colorectal cancer cell lines. Moreover, MTT (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide) assay of CNCs/β-CD+/PIA complexes showed significant dose-dependent phototoxicity after illumination with red light, with IC50 values of 2.5 and 8.7 nM, for HT 116 and HT-29, respectively, and very low dark toxicity. The current results suggest that these nanoparticle/photosensitizer complexes are promising and useful tools for photodynamic therapy (PDT).
ISSN:1878-1543

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