Phthalocyanine functionalized poly(vinyl alcohol)s via CuAAC click chemistry and their antibacterial properties

Gürol, İlke; Altınkök, Çağatay; Agel, Esra; Taşaltın, Cihat; Durmuş, Mahmut; Açık, Gökhan

doi:10.1007/s11998-020-00363-y

Cited by 13 publications

(7 citation statements)

References 54 publications

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“…In addition to this, the solvents used for click chemistry should be biorenewable and biodegradable and capable of dissolving a wide range of compounds. The classic examples of organic solvents employed in click chemistry are t -butanol, , tetrahydrofuran, toluene, dichloromethane, acetonitrile, dimethylformamide, dimethyl sulfoxide, and ethanol . Alternatively, green solvents have been used in click reactions to replace the traditional organic solvents, as they are nontoxic, biorenewable, and environmentally friendly. , Green solvents like water, glycerol, γ-valerolactone, 2-methyl-THF, and lactic acid have received wide attention from the synthetic chemists for use in click conjugation reactions.…”

Section: Huisgen 13-dipolar Cycloaddition Reactionmentioning

confidence: 99%

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

2021

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Cu(I)-catalyzed azide−alkyne cycloaddition (CuAAC) is a modular and bioorthogonal approach that is being adopted for the efficient synthesis of organic and bioorganic compounds. It leads to the selective formation of 1,4-disubstituted 1,2,3-triazole units connecting readily accessible building blocks via a stable and biocompatible linkage. The vast array of the bioconjugation applications of click chemistry has been attributed to its fast reaction kinetics, quantitative yields, minimal byproducts, and high chemospecificity and regioselectivity. These combined advantages make click reactions quite suitable for the lead identification and the development of pharmaceutical agents in the fields of medicinal chemistry and drug discovery. In this review, we have outlined the key aspects, the mechanistic details and merits and demerits of the click reaction. In addition, we have also discussed the recent pharmaceutical applications of click chemistry, ranging from the development of anticancer, antibacterial, and antiviral agents to that of biomedical imaging agents and clinical therapeutics.

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Section: Huisgen 13-dipolar Cycloaddition Reactionmentioning

confidence: 99%

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

2021

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“…They exhibited high antibacterial activities against both Gram-negative bacteria (Escherichia coli and Salmonella typhimurium) and Gram-positive bacteria (Staphylococcus aureus and Listeria monocytogenes). 32 Besides, antimicrobial photodynamic therapy (APDT) is well known as a treatment technique not leading to microorganism resistance. This method includes three main components (light, photosensitizer, and oxygen).…”

Section: ■ Introductionmentioning

confidence: 99%

“…Gurol et al synthesized a series of zinc(II) phthalocyanine (ZnPc)-based poly(vinyl alcohol)s (PVA-Pcs) and examined their antibacterial properties. They exhibited high antibacterial activities against both Gram-negative bacteria (Escherichia coli and Salmonella typhimurium) and Gram-positive bacteria (Staphylococcus aureus and Listeria monocytogenes) . Besides, antimicrobial photodynamic therapy (APDT) is well known as a treatment technique not leading to microorganism resistance.…”

Section: Introductionmentioning

confidence: 99%

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

Farajzadeh Öztürk,

Özdemir,

Yalçın

et al. 2024

ACS Appl. Bio Mater.

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This study presents a tetra-substituted phthalonitrile derivative, namely, diethyl 2-(3,4dicyano-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.

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“…PVA–Pc complex revealed a higher inhibitory effect on bacteria compared to pure PVA and many antibiotics. 18 Nickel (Ni)-coordinated Pcs (NiPc) were introduced as a photodynamic antibacterial agent. Accordingly, the achiral NiPc showed excellent Fenton-like activity under light illumination and also exhibited superior antibacterial effects on E. coli and S. aureus .…”

Section: Introductionmentioning

confidence: 99%

Superior photo-induced antibacterial/antibiofilm activities of ZnPcs/TiO₂ and computational simulation studies

Özcan,

Çekceoğlu,

Al-Khafaji

et al. 2023

J. Mater. Chem. B

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Phthalocyanine functionalized poly(vinyl alcohol)s via CuAAC click chemistry and their antibacterial properties

Cited by 13 publications

References 54 publications

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

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

Superior photo-induced antibacterial/antibiofilm activities of ZnPcs/TiO₂ and computational simulation studies

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Phthalocyanine functionalized poly(vinyl alcohol)s via CuAAC click chemistry and their antibacterial properties

Cited by 13 publications

References 54 publications

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

An Overview of Recent Advances in Biomedical Applications of Click Chemistry

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

Superior photo-induced antibacterial/antibiofilm activities of ZnPcs/TiO2 and computational simulation studies

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Superior photo-induced antibacterial/antibiofilm activities of ZnPcs/TiO₂ and computational simulation studies