Biological Performance of Hexadeca-Substituted Metal Phthalocyanine/Reduced Graphene Oxide Nanobioagents

This study presents a tetra-substituted phthalonitrile derivative, namely, diethyl 2-(3,4-dicyano-2,5-bis­(hexyloxy)-6-(4-(trifluoromethoxy)­phenoxy)­phenyl)­malonate (a), cyclotetramerizing in the presence of some metal salts. The resultant hexadeca-substituted metal phthalocyanines [M= Co, Zn, InC...

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Bibliographic Details
Published in:ACS applied bio materials 2024-05, Vol.7 (5), p.3215-3226
Main Authors: Farajzadeh Öztürk, Nazlı, Özdemir, Sadin, Yalçın, Mustafa Serkan, Tollu, Gülşah, Altuntaş Bayır, Zehra, Koçak, Makbule Burkut
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antioxidants - chemical synthesis
Antioxidants - chemistry
Antioxidants - pharmacology
Biocompatible Materials - chemical synthesis
Biocompatible Materials - chemistry
Biocompatible Materials - pharmacology
Biofilms - drug effects
Cell Survival - drug effects
Escherichia coli - drug effects
Graphite - chemistry
Graphite - pharmacology
Humans
Indoles - chemistry
Indoles - pharmacology
Isoindoles
Materials Testing
Microbial Sensitivity Tests
Molecular Structure
Oxides - chemistry
Oxides - pharmacology
Particle Size
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Summary:This study presents a tetra-substituted phthalonitrile derivative, namely, diethyl 2-(3,4-dicyano-2,5-bis­(hexyloxy)-6-(4-(trifluoromethoxy)­phenoxy)­phenyl)­malonate (a), cyclotetramerizing in the presence of some metal salts. The resultant hexadeca-substituted metal phthalocyanines [M= Co, Zn, InCl)] (b–d) were used for the modification of reduced graphene oxide for the first time. The effect of the phthalonitrile/metal phthalocyanines on biological features of reduced graphene oxide (rGO) was extensively examined by the investigation of antioxidant, antimicrobial, DNA cleavage, cell viability, and antibiofilm activities of nanobioagents (1–4). The results were compared with those of unmodified rGO (nanobioagent 5), as well. Modification of reduced graphene oxide with the synthesized compounds improved its antioxidant activity. The antioxidant activities of all the tested nanobioagents also enhanced as the concentration increased. The antibacterial activities of all the nanobioagents improved by applying the photodynamic therapeutic (PDT) method. All the phthalonitrile/phthalocyanine-based nanobioagents (especially phthalocyanine-based nanocomposites) exhibited DNA cleavage activities, and complete DNA fragmentation was observed for nanobioagents (1–4) at 200 mg/L. They can be used as potent antimicrobial and antimicrobial photodynamic therapy agents as well as Escherichia coli microbial cell inhibitors. As a result, the prepared nanocomposites can be considered promising candidates for biomedicine.
ISSN:2576-6422
2576-6422
DOI:10.1021/acsabm.4c00215