Antimicrobial and antioxidant properties of novel octa-substituted phthalocyanines bearing (trifluoromethoxy) phenoxy groups on peripheral positions

Farajzadeh, Nazli; Karaoğlu, Hande Pekbelgin; Akın, Mustafa; Şaki, Neslihan

doi:10.1142/s1088424619500068

Cited by 28 publications

(20 citation statements)

References 53 publications

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“…In another study, Farajzadeh et al determined the antioxidant activity of novel octasubstituted Pcs bearing (trifluoromethoxy) phenoxy groups in the peripheral positions. When the results were compared, all tested water-soluble Pcs containing quinoline 5-sulfonic acid groups exhibited much better reducing power activity at much lower concentration levels [29].…”

Section: Determination Of Reducing Power Capacitymentioning

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: Determination Of Reducing Power Capacitymentioning

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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“…The respective Q‐bands of compounds 3 and 4 were observed at 687 and 676 nm, whereas, the B‐bands appeared at 355 and 325 nm, respectively. As shown in Figure , The Q‐bands of the synthesized Pcs are in 3 > 4 depending on the central metal ion . The Log ϵ values of the macrocyclic molecules 3 and 4 are given in Table .…”

Section: Resultsmentioning

confidence: 95%

“…Compound 3 obeyed Lambert‐Beer law in various concentrations of DCM at from 4×10 −6 to 14×10 −6 M (Figure ). As the concentration of the substance increases, the density of the Q band causes an increase parallel to this increase and no new band is observed due to aggregation . In addition, the electronic absorption spectra of 3 in various organic solvents including acetone, EtAc, THF, DCM, DMF and CHCl 3 were investigated (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Investigation of Time‐Kill Evaluation and Antioxidant Activities of New Tetra‐Substituted Metallophthalocyanines Bearing 4‐(Trifluoromethoxy)thiophenyl Groups

et al. 2020

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In the present work, a new phthalonitrile derivative bearing 4‐(trifluoromethoxy)‐thiophenyl group at the 4‐position (2) has been synthesized. Cyclotetramerization of 4‐[4‐(trifluoromethoxy)‐thiophenyl] phthalonitrile (2) in appropriate high‐boiling solvents gave the desired peripherally tetra‐substituted zinc ({2(3),9(10),16(17),23(24)‐tetrakis‐[4‐(trifluoromethoxy)‐thiophenyl]‐phthalocyaninato} zinc(II) (3)) and cobalt phthalocyanines ({2(3),9(10),16(17),23(24)‐tetrakis‐[4‐(trifluoromethoxy)‐ thiophenyl]‐phthalocyaninato} cobalt(II) (4)). The resulting phthalonitrile and phthalocyanine derivatives were characterized by the 1H NMR, 13C NMR, 19F NMR, elemental analysis, UV‐Vis, FT‐IR and mass spectrometric methods. Aggregation properties of macrocycle 3 were investigated in the different concentrations and various solvents. The biological activities of the newly synthesized compounds were investigated by using well diffusion and growth curve kinetic assay. In both methods, the molecules exhibited inhibition effect only on gram negative bacteria. According to the results; molecule 4 showed the highest inhibition activity at both tested concentrations. Antioxidant activities were also evaluated by using 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) and reducing power assays and the molecules performed moderate antioxidant activity.

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“…Since compound 1a obeys the Lambert–Beer law, aggregation does not rely on concentration at the studied range of concentration (Fig. 5) (29–34,41,42).…”

Section: Resultsmentioning

confidence: 99%

Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

Sağlam

Farajzadeh

Atmaca

et al. 2020

Photochem & Photobiology

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This study presents the preparation of a new phthalonitrile derivative namely 3‐(4‐(trifluoromethoxy)thiophenoxy)phthalonitrile (1) and a series of its metallated phthalocyanines (M = Zn (II) (1a) and In(III) (1b)). In addition, the peripheral analog of the indium phthalocyanine chloride (2b) was newly synthesized. Characterization of the resulting compounds was carried out by utilizing various spectroscopic methods such as FT‐IR, 1H NMR and UV‐Vis spectroscopy. The influence of concentration on aggregation properties of compound 1a was investigated at different concentrations of DMSO. The effect of solvent type on aggregation properties of compound 1a was studied, as well. According to the referred procedures, the macrocyclic molecules (2a, 3a‐b and 4a‐b) were prepared. The effect of some parameters including metal ion, the position of the substituent and the connected atom (oxo or thio) on photochemical and photophysical features of compounds (1a‐b, 2a‐b, 3a‐b, and 4a‐b) was studied for evaluation of their potential as a photosensitizer in PDT, comparatively. The highest singlet oxygen quantum yields (ΦΔ = 0.71 for 1a and 0.80 for 2b) were obtained for complexes 1a and 1b in DMSO. The photophysical and photochemical features of the studied macromolecules are therefore suitable for photodynamic therapy applications.

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Antimicrobial and antioxidant properties of novel octa-substituted phthalocyanines bearing (trifluoromethoxy) phenoxy groups on peripheral positions

Cited by 28 publications

References 53 publications

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

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

Investigation of Time‐Kill Evaluation and Antioxidant Activities of New Tetra‐Substituted Metallophthalocyanines Bearing 4‐(Trifluoromethoxy)thiophenyl Groups

Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

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