Synthesis and photophysicochemical properties of novel thiadiazole-substituted zinc (II), gallium (III) and silicon (IV) phthalocyanines for photodynamic therapy

Güzel, Emre; Günsel, Armağan; Bilgiçli, Ahmet T.; Atmaca, Göknur Yaşa; Erdoğmuş, Alı; Yaraşir, M. Nilüfer

doi:10.1016/j.ica.2017.07.058

Cited by 51 publications

(26 citation statements)

References 40 publications

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“…The solubility in common organic solvents and water can be enhanced by the introduction of bulky or long chain groups, e.g., alkyl, sulfonate, carboxy, or alkoxy on the peripheral positions and nonperipheral positions of the Pc macrocycle, and this causes the formation of additional solvation centers. Water-soluble Pcs are of great scientific and technological importance, such as in PDT and medical applications [14][15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Antioxidant properties of water-soluble phthalocyanines containing quinoline5-sulfonic acid groups

Günsel¹,

Alıcı²,

Bilgiçli³

et al. 2019

Turk J Chem

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In the present study, the antioxidant properties of peripherally and nonperipherally water-soluble tetra (quinoline 5-sulfonic acid) substituted metal-free (1, 2), Zn(II) (3, 4), Co(II) (5, 6), and Mn(III)Cl (7, 8) phthalocyanine (Pc) derivatives were reported. In order to determine the antioxidant properties of the Pc compounds, three different commonly known antioxidant methods were used: DPPH (α , α-diphenylβ-picrylhydrazyl) radical scavenging, ferrous ion chelating, and reducing power assays. Compound 6 showed the best DPPH activity among the other tested compounds except for the standards. The ferrous ion chelating IC 50 value of compound 7 was nearly as good as that of the EDTA standard. The reducing power activity results indicated that the tested Pc compounds were as sensitive as standard reducing agents such as butylated hydroxytoluene and ascorbic acid. Overall, all tested compounds showed good antioxidant properties and it may be suggested that they could be used as new positive controls for reducing power assays in the future works.

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Section: Introductionmentioning

confidence: 99%

Antioxidant properties of water-soluble phthalocyanines containing quinoline5-sulfonic acid groups

Günsel¹,

Alıcı²,

Bilgiçli³

et al. 2019

Turk J Chem

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“…Phthalocyanines (Pcs), which are an important family of the macrocyclic compounds class, have many uses, e.g., as gas sensors, catalysts, solar cells, electrochromic devices, Langmuir Blodgett films, liquid crystals, and photosensitizers, in photodynamic cancer therapy (PDT). Photodynamic cancer therapy from these areas of use is very important in their studies of elimination of the tumor tissues without the need for surgical intervention.…”

Section: Introductionmentioning

confidence: 99%

Aminopyrazole‐substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties

Güzel

Koçyiğit

Arslan

et al. 2019

Archiv der Pharmazie

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The synthesis, characterization, aggregation behavior, theoretical studies, and investigation of antimicrobial, antidiabetic, and anticholinergic properties of 4-(2-(5amino-4-(4-bromophenyl)-3-methyl-1H-pyrazol-1-yl)ethoxy)phthalonitrile (2) and its soluble aminopyrazole-substituted peripheral metallo (Mn, Co, and Ni)-phthalocyanine complexes (3-5) are reported for the first time. The synthesized compounds and phthalocyanine complexes were characterized spectroscopically. The new phthalonitrile derivative (2) and its peripheral metallophthalocyanine complexes (3-5) were found to be effective inhibitors of α-glycosidase, acetylcholinesterase (AChE), human carbonic anhydrase I and II isoforms (hCA I and II), and butyrylcholinesterase (BChE) with K i values in the range of 1.55 ± 0.47 to 10.85 ± 3.43 nM for α-glycosidase,8.44 ± 0.32 to 21.31 ± 7.91 nM for hCA I, 11.73 ± 2.82 to 31.03 ± 4.81 nM for hCA II, 101.62 ± 26.58 to 326.54 ± 89.67 nM for AChE, and 68.68 ± 11.15 to 109.53 ± 19.55 nM for BChE. This is the first study of peripherally substituted phthalocyanines containing an aminopyrazole group as potential carbonic anhydrase enzyme inhibitor. Also, the antimicrobial activities of the synthesized compounds were evaluated against six microorganisms (four bacteria and two Candida species) using the broth microdilution method. The gram-positive bacteria were detected to be more sensitive than gram-negative bacteria and yeasts in the synthesized compounds. K E Y W O R D S acetylcholinesterase, anticholinergic, antidiabetic, antimicrobial, aminopyrazole, carbonic anhydrase, phthalocyanine

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“…It is known that the metal atom coordinating to the phthalocyanine ring can significantly change the physical and chemical properties of the complex . Particularly zinc metal coordinated phthalocyanine complexes have been preferred in the photodynamic therapy of cancer due to the closed shell, diamagnetic ion (Zn 2+ ) give both high triplet quantum yields and long lifetimes . Up to this time, many photosensitizers have been tested in vitro and in vivo in PDT experiments, but few of them have shown ideal properties.…”

Section: Introductionmentioning

confidence: 99%

“…[15][16][17] Particularly zinc metal coordinated phthalocyanine complexes have been preferred in the photodynamic therapy of cancer due to the closed shell, diamagnetic ion (Zn 2 + ) give both high triplet quantum yields and long lifetimes. [18] Up to this time, many photosensitizers have been tested in vitro and in vivo in PDT experiments, but few of them have shown ideal properties. This has led to a focus on the development of new photosensitizer and the enhancement of their effectiveness.…”

Section: Introductionmentioning

confidence: 99%

High Photosensitized Singlet Oxygen Generating Zinc and Chloroindium Phthalocyanines Bearing (4‐isopropylbenzyl)oxy Groups as Potential Agents for Photophysicochemical Applications

et al. 2019

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In this study, novel phthalonitrile derivatives (1 and 2) and their peripherally and non‐peripherally tetra (4‐isopropylbenzyl)oxy‐substituted zinc and chloroindium phthalocyanine complexes (3‐6) have been prepared for the first time. The synthesized phthalonitrile derivatives and phthalocyanine complexes were characterized spectroscopically. Not only the chloroindium phthalocyanines but also zinc phthalocyanines are essentially free from aggregation in THF at the studied micromolar concentration. The purpose is to compare the effects of two types of substitution on the phthalocyanines to be used as sensitizers in photodynamic therapy (PDT). Photophysical and photochemical properties of all phthalocyanines are investigated and the results showed that the peripheral phthalocyanines more effectively photooxidize DPBF through singlet oxygen. The photochemical results showed that both ZnPc (3 and 5) and InPc (4 and 6) can be used as sensitizers in PDT because of their very high singlet oxygen quantum yields (range from 0.80 to 0.97).

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Synthesis and photophysicochemical properties of novel thiadiazole-substituted zinc (II), gallium (III) and silicon (IV) phthalocyanines for photodynamic therapy

Cited by 51 publications

References 40 publications

Antioxidant properties of water-soluble phthalocyanines containing quinoline5-sulfonic acid groups

Antioxidant properties of water-soluble phthalocyanines containing quinoline5-sulfonic acid groups

Aminopyrazole‐substituted metallophthalocyanines: Preparation, aggregation behavior, and investigation of metabolic enzymes inhibition properties

High Photosensitized Singlet Oxygen Generating Zinc and Chloroindium Phthalocyanines Bearing (4‐isopropylbenzyl)oxy Groups as Potential Agents for Photophysicochemical Applications

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