Graphene Oxide/Cholesterol-Substituted Zinc Phthalocyanine Composites with Enhanced Photodynamic Therapy Properties

In the present work, cholesterol (Chol)-substituted zinc phthalocyanine (Chol-ZnPc) and its composite with graphene oxide (GO) were prepared for photodynamic therapy (PDT) applications. Briefly, Chol-substituted phthalonitrile (Chol-phthalonitrile) was synthesized first through the substitution of C...

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Bibliographic Details
Published in:Materials 2023-11, Vol.16 (22), p.7060
Main Author: Erden, Fuat
Format: Article
Language:English
Subjects:
Active oxygen
Antioxidants
Cancer
Cancer therapies
Care and treatment
Chemical analysis
Cholesterol
Chromatography
Graphene
Graphite
Lipoproteins
Low density lipoprotein receptors
NMR
Nuclear magnetic resonance
Photodynamic therapy
Phthalocyanins
Potash
Potassium
Singlet oxygen
Spectrum analysis
Substitution reactions
Toxicity
Zinc chloride
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Summary:In the present work, cholesterol (Chol)-substituted zinc phthalocyanine (Chol-ZnPc) and its composite with graphene oxide (GO) were prepared for photodynamic therapy (PDT) applications. Briefly, Chol-substituted phthalonitrile (Chol-phthalonitrile) was synthesized first through the substitution of Chol to the phthalonitrile group over the oxygen bridge. Then, Chol-ZnPc was synthesized by a tetramerization reaction of Chol-phthalonitrile with ZnCl2 in a basic medium. Following this, GO was introduced to Chol-ZnPc, and the successful preparation of the samples was verified through FT-IR, UV–Vis, 1H-NMR, MALDI-TOF MS, SEM, and elemental analysis. Regarding PDT properties, we report that Chol-ZnPc exhibited a singlet oxygen quantum yield (Φ∆) of 0.54, which is slightly lower than unsubstituted ZnPc. Upon introduction of GO, the GO/Chol-ZnPc composite exhibited a higher Φ∆, about 0.78, than that of unsubstituted ZnPc. Moreover, this enhancement was realized with a simultaneous improvement in fluorescence quantum yield (ΦF) to 0.36. In addition, DPPH results suggest low antioxidant activity in the composite despite the presence of GO. Overall, GO/Chol-ZnPc might provide combined benefits for PDT, particularly in terms of image guidance and singlet oxygen generation.
ISSN:1996-1944
1996-1944
DOI:10.3390/ma16227060