3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy groups substituted phthalocyanines: Synthesis, characterization and their biological properties

Başak Sezgi Bilen; Mukaddes Özçeşmeci; Mustafa Akın; Büşra Çakır; Karrar Ali Mohammed Hasan Alsakini; Ayşe Nalbantsoy; Neslihan Şaki; Esin Hamuryudan

doi:10.1016/j.dyepig.2023.111814

3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy groups substituted phthalocyanines: Synthesis, characterization and their biological properties

Başak Sezgi Bilen, Mukaddes Özçeşmeci, Mustafa Akın, Büşra Çakır, Karrar Ali Mohammed Hasan Alsakini, Ayşe Nalbantsoy, Neslihan Şaki, Esin Hamuryudan^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

In this study, 3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy group substituted metal-free and metallo-phthalocyanines have been synthesized. The new compounds have been characterized by a combination of several spectroscopic techniques. Using 1,1-diphenyl-2-picrylhydrazine (DPPH), OH radical scavenging, and reducing power tests, the antioxidant properties of these phthalocyanines were assessed. CoPc showed the highest antioxidant activity for DPPH assay, ZnPc and MnPc exhibited the highest and smilar antioxidant activity at reducing power assay, ZnPc demonstrated the highest antioxidant activity at OH scavenging activity. By using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, cytotoxicity of phthalocyanines was evaluated, and iNOS mediated nitric oxide (NO) generation was carried out.

Original language	English
Article number	111814
Journal	Dyes and Pigments
Volume	221
DOIs	https://doi.org/10.1016/j.dyepig.2023.111814
Publication status	Published - Jan 2024

Bibliographical note

Publisher Copyright:
© 2023 Elsevier Ltd

Funding

This work was supported by Research Fund of the Istanbul Technical University and Research Fund of the Kocaeli University (Project No: BAP-2022/2807 ).

Funders	Funder number
Kocaeli Üniversitesi	BAP-2022/2807
Istanbul Teknik Üniversitesi

Keywords

Antioxidant
Cytotoxicity
NO production
Phthalocyanine
Synthesis

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10.1016/j.dyepig.2023.111814

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Bilen, B. S., Özçeşmeci, M., Akın, M., Çakır, B., Alsakini, K. A. M. H., Nalbantsoy, A., Şaki, N., & Hamuryudan, E. (2024). 3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy groups substituted phthalocyanines: Synthesis, characterization and their biological properties. Dyes and Pigments, 221, Article 111814. https://doi.org/10.1016/j.dyepig.2023.111814

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abstract = "In this study, 3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy group substituted metal-free and metallo-phthalocyanines have been synthesized. The new compounds have been characterized by a combination of several spectroscopic techniques. Using 1,1-diphenyl-2-picrylhydrazine (DPPH), OH radical scavenging, and reducing power tests, the antioxidant properties of these phthalocyanines were assessed. CoPc showed the highest antioxidant activity for DPPH assay, ZnPc and MnPc exhibited the highest and smilar antioxidant activity at reducing power assay, ZnPc demonstrated the highest antioxidant activity at OH scavenging activity. By using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, cytotoxicity of phthalocyanines was evaluated, and iNOS mediated nitric oxide (NO) generation was carried out.",

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year = "2024",

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doi = "10.1016/j.dyepig.2023.111814",

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AU - Bilen, Başak Sezgi

AU - Özçeşmeci, Mukaddes

AU - Akın, Mustafa

AU - Çakır, Büşra

AU - Alsakini, Karrar Ali Mohammed Hasan

AU - Nalbantsoy, Ayşe

AU - Şaki, Neslihan

AU - Hamuryudan, Esin

PY - 2024/1

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N2 - In this study, 3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy group substituted metal-free and metallo-phthalocyanines have been synthesized. The new compounds have been characterized by a combination of several spectroscopic techniques. Using 1,1-diphenyl-2-picrylhydrazine (DPPH), OH radical scavenging, and reducing power tests, the antioxidant properties of these phthalocyanines were assessed. CoPc showed the highest antioxidant activity for DPPH assay, ZnPc and MnPc exhibited the highest and smilar antioxidant activity at reducing power assay, ZnPc demonstrated the highest antioxidant activity at OH scavenging activity. By using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, cytotoxicity of phthalocyanines was evaluated, and iNOS mediated nitric oxide (NO) generation was carried out.

AB - In this study, 3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy group substituted metal-free and metallo-phthalocyanines have been synthesized. The new compounds have been characterized by a combination of several spectroscopic techniques. Using 1,1-diphenyl-2-picrylhydrazine (DPPH), OH radical scavenging, and reducing power tests, the antioxidant properties of these phthalocyanines were assessed. CoPc showed the highest antioxidant activity for DPPH assay, ZnPc and MnPc exhibited the highest and smilar antioxidant activity at reducing power assay, ZnPc demonstrated the highest antioxidant activity at OH scavenging activity. By using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, cytotoxicity of phthalocyanines was evaluated, and iNOS mediated nitric oxide (NO) generation was carried out.

KW - Antioxidant

KW - Cytotoxicity

KW - NO production

KW - Phthalocyanine

KW - Synthesis

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M3 - Article

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ER -

3′,3′,4′,4′,5′,5′,6′,6′,6′-nonafluoro-hexyloxy groups substituted phthalocyanines: Synthesis, characterization and their biological properties

Abstract

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Keywords

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