Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine

Emre Güzel; Armaǧan Atsay; Sevgi Nalbantoglu; Neslihan Şaki; A. Lale Dogan; Ahmet Gül; Makbule Burkut Koçak

doi:10.1016/j.dyepig.2012.12.027

Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine

Emre Güzel, Armaǧan Atsay, Sevgi Nalbantoglu, Neslihan Şaki, A. Lale Dogan, Ahmet Gül, Makbule Burkut Koçak^*

^*Corresponding author for this work

Department of Chemistry

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

99 Citations (Scopus)

Abstract

A new phthalonitrile derivative bearing hexyloxy groups in the 3,6- positions and p-sulfonylphenoxy- and chloro groups in the 4 and 5- positions was synthesized. The new hexadeca-substituted zinc phthalocyanine was obtained by cyclotetramerisation of this phthalonitrile derivative in the presence of anhydrous zinc acetate under microwave heating. The aggregation behavior of the amphiphilic zinc phthalocyanine was studied in methanol and water. All novel compounds have been characterized by using elemental analysis, UV-Vis, FT-IR, ¹H NMR and MS spectroscopic data. The photosensitizing activity of this phthalocyanine dye was evaluated by application of 1,3- diphenylisobenzofuran as a singlet oxygen chemical quencher. In cell culture media the phthalocyanine showed a cytotoxic effect on HepG2 cells; a feature which encourages future in vivo studies.

Original language	English
Pages (from-to)	238-243
Number of pages	6
Journal	Dyes and Pigments
Volume	97
Issue number	1
DOIs	https://doi.org/10.1016/j.dyepig.2012.12.027
Publication status	Published - Apr 2013

Keywords

Amphiphilic
Hexadeca-substituted
In-vitro
Microwave irradiation
Photosensitizing activity
Phthalocyanine

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10.1016/j.dyepig.2012.12.027

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title = "Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine",

abstract = "A new phthalonitrile derivative bearing hexyloxy groups in the 3,6- positions and p-sulfonylphenoxy- and chloro groups in the 4 and 5- positions was synthesized. The new hexadeca-substituted zinc phthalocyanine was obtained by cyclotetramerisation of this phthalonitrile derivative in the presence of anhydrous zinc acetate under microwave heating. The aggregation behavior of the amphiphilic zinc phthalocyanine was studied in methanol and water. All novel compounds have been characterized by using elemental analysis, UV-Vis, FT-IR, 1H NMR and MS spectroscopic data. The photosensitizing activity of this phthalocyanine dye was evaluated by application of 1,3- diphenylisobenzofuran as a singlet oxygen chemical quencher. In cell culture media the phthalocyanine showed a cytotoxic effect on HepG2 cells; a feature which encourages future in vivo studies.",

keywords = "Amphiphilic, Hexadeca-substituted, In-vitro, Microwave irradiation, Photosensitizing activity, Phthalocyanine",

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AU - Güzel, Emre

AU - Atsay, Armaǧan

AU - Nalbantoglu, Sevgi

AU - Şaki, Neslihan

AU - Dogan, A. Lale

AU - Gül, Ahmet

AU - Koçak, Makbule Burkut

PY - 2013/4

Y1 - 2013/4

N2 - A new phthalonitrile derivative bearing hexyloxy groups in the 3,6- positions and p-sulfonylphenoxy- and chloro groups in the 4 and 5- positions was synthesized. The new hexadeca-substituted zinc phthalocyanine was obtained by cyclotetramerisation of this phthalonitrile derivative in the presence of anhydrous zinc acetate under microwave heating. The aggregation behavior of the amphiphilic zinc phthalocyanine was studied in methanol and water. All novel compounds have been characterized by using elemental analysis, UV-Vis, FT-IR, 1H NMR and MS spectroscopic data. The photosensitizing activity of this phthalocyanine dye was evaluated by application of 1,3- diphenylisobenzofuran as a singlet oxygen chemical quencher. In cell culture media the phthalocyanine showed a cytotoxic effect on HepG2 cells; a feature which encourages future in vivo studies.

AB - A new phthalonitrile derivative bearing hexyloxy groups in the 3,6- positions and p-sulfonylphenoxy- and chloro groups in the 4 and 5- positions was synthesized. The new hexadeca-substituted zinc phthalocyanine was obtained by cyclotetramerisation of this phthalonitrile derivative in the presence of anhydrous zinc acetate under microwave heating. The aggregation behavior of the amphiphilic zinc phthalocyanine was studied in methanol and water. All novel compounds have been characterized by using elemental analysis, UV-Vis, FT-IR, 1H NMR and MS spectroscopic data. The photosensitizing activity of this phthalocyanine dye was evaluated by application of 1,3- diphenylisobenzofuran as a singlet oxygen chemical quencher. In cell culture media the phthalocyanine showed a cytotoxic effect on HepG2 cells; a feature which encourages future in vivo studies.

KW - Amphiphilic

KW - Hexadeca-substituted

KW - In-vitro

KW - Microwave irradiation

KW - Photosensitizing activity

KW - Phthalocyanine

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M3 - Article

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SN - 0143-7208

VL - 97

SP - 238

EP - 243

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 1

ER -

Synthesis, characterization and photodynamic activity of a new amphiphilic zinc phthalocyanine

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Keywords

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