Browsing by Author "Agirtas, M. Salih"

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2, 10, 16, 24-tetrakis 4- (2-fenoksi-l, 3-diokso-2,3-dihidro-lh-inden-2-iloksi) Ftalonitril İçeren Kobalt (Ii) Bileşiğinin Dna Bağlanmasının Spektroskopik Yöntemler ile Araştırılması
(2017) Agirtas, M. Salih; Arslantaş, Ali
2,10, 16, 24-tetrakis 4- (2-fenoksi-1,3-diokso-2,3-dihidro-lH-inden-2-iloksi) ftalonitril içeren önceden sentezlenmiş kobalt (II) bileşiğinin (PcCo) CT-DNA ile bağlanma özellikleri UV/Vis absorpsiyon, floresan titrasyonu yöntemleri kullanılarak bağlanma özelliklerini belirlemek için araştırıldı. DMF çözücü ortamında ve DNA'nın yokluğunda, PcCo'nun absorpsiyon titrasyon spektrumu, Q-band için yaklaşık 670 nm'de pik ve B -bandı için 340 nm de pik verir. Calf thymus-DNA, PcCo varlığında PcCo'nun emisyon yoğunluğu yaklaşık 545 nm'de emisyona neden olur. Termal denatürasyon profili çalışması UV-Vis spektroskopik tekniği ile sistematik olarak incelenmiş ve Co (II) ftalosiyanin bileşiği için erime noktası sıcaklık değeri 7.87 oC civarında bulunmuştur. CTDNA yokluğunda ve varlığında PcCo'in redüksiyon oksidasyon davranışı, dönüşümlü voltametri (CV) ile incelendi. PcCo için katodik pik ve anodik pik potansiyelleri, EPc için 0.84, -0.36 V ve 0.88 V, 0.15 V ve EPa için -0.69 V olarak kaydedildi. Dönüşümlü (cyclic) voltametri sonuçlar, bir yarı-tersinir redaksiyon oksidasyon dalgasını göstermektedir. Epc ve Epa potansiyelindeki değişim, PcCo'in CT-DNA'yla güçlü etkileşim gösterdiğini önermektedir. PcCo'in CT-DNA ile olan etkileşimi ayrıca jel elektroforez yöntemi kullanılarak araştırılmıştır. Jel elektroforezi sonuçları, CT-DNA bantlarının yoğunluğunda azalma olduğunu gösterdi. Tüm bulgular, PcCo ile CT-DNA molekülü arasındaki etkileşimin interkalatif bağlanma türü olduğunu göstermektedir.
Design of Novel Binuclear Phthalocyanines Formed by Dioxyphenyl Bridges: Synthesis and Investigation of Thermal and Antioxidant Properties
(Wiley-v C H verlag Gmbh, 2012) Agirtas, M. Salih; Gumus, Ilkay; Okumus, Veysi; Dundar, Abdurrahman
4, 4'-(1, 4-Phenylenebis(oxy)diphthalonitrile was synthesized by reaction of hydroquinone with 4-nitrophthalonitrile. Binuclear metallophthalocyanines 24 were obtained by the reaction between 4, 4'-(1, 4-phenylenebis(oxy)diphthalonitrile and 4-(benzo [d] 1,3 dioxol-5-ylmethoxy)phthalonitrile in the presence of metal salts. These new compounds were characterized by using elemental analysis, FTIR, 1H-NMR and UV/Vis spectroscopic data. Thermal properties of phthalocyanines 2-4 were investigated by TG and DTA. In addition, antioxidant properties of compounds II, 3 and 4 were investigated. Their radical-scavenging capacity and chelating effects was fully studied. The maximum 1, 1-diphenyl-2-picrylhydrazyl radicals (DPPH) were obtained from compound 3. Chelating effects on ferrous ions were 91.6?% at concentration of 100 mg?L1 with compound II.
Designing of New Thermo Stabile Phthalocyanines: Synthesis, Characterization, and Thermal Studies
(Taylor & Francis inc, 2012) Agirtas, M. Salih; Gumus, Ilkay; Izgi, M. Sait
In this study, new phthalonitrile and phthalocyanines were synthesized and characterized. Starting material compound 3 was obtained by reaction of ninhydrin with 4-nitrophthalonitrile. Phthalocyanines 4-8 were prepared by reaction 4-(2-phenoxy-1, 3-dioxo-2, 3-dihydro-1H-inden-2-yloxy) phthalonitrile with corresponding metal salts. Compound 9 was obtained by reaction of phthaocyanine 4 with NaOH. This compound is soluble in water as sodium salts. Thermal properties of compounds 3-8 were investigated by TG and DTA. Thermal stabilities of compounds 4-8 are also reported. The novel compounds were characterized by elemental analysis, FTIR, H-1-NMR, and UV-VIS spectral data.
Dna Cleavage Properties and Synthesis of Metallophthalocyanines With 5-Methyl Triazolo [1, 5-A] Pyrimidin-7 Substituents
(Taylor & Francis inc, 2017) Agirtas, M. Salih; Ondes, M. Yusuf; Ozdemir, Sadin; Okumus, Veysi
The aim of the present study is to perform synthesis of novel metallophthalocyanines (pcs) with high solubility. The synthesis and characterization of 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-yloxy-substituted zinc, magnesium, and cobalt pcs are reported. These compounds have been characterized using electronic absorption, nuclear magnetic resonance spectroscopy, infrared, elemental analysis and mass spectra. The aggregation investigations carried out in different concentrations indicate that 5-methyl-[1, 2, 4] triazolo [1, 5-a] pyrimidin-7-yloxy-substituted pc complexes do not have any aggregation behavior for the concentration range of 1 x 10(-5) -1 x 10(-6) M in THF. DPPH radical scavenging activity, metal chelating activity, and reducing power of the compounds were evaluated. The DNA gel electrophoresis studies revealed that new phthalonitrile and its metallophthalocyanine compounds cleavaged plasmid DNA (pBR322). Additionally, the ground-state geometries of the complexes were optimized using density functional theory methods at B3LYP/6-31G (d, p) level in order to obtain information about the 3D geometries and electronic structure.
Metallo and Metal Free Phthalocyanines Bearing (4-(1(4 Substituents: Synthesis, Characterization, Aggregation Behavior, Electronic, Antioxidant and Antibacterial Properties
(Elsevier Science Sa, 2014) Agirtas, M. Salih; Guven, M. Emin; Gumus, Selcuk; Ozdemir, Sadin; Dundar, Abdurrahman
As starting material the phthalonitrile derivative bearing (4-(1(4-phenoxyphenyl)-1-phenylethyl)phenol substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile derivative in the presence of corresponding metal salts gave the new metallophthalocyanines. Metal free phthalocyanine was obtained from the reaction of 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalonitrile units. The novel compounds have been characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that 4-(4-(1-(4-hydroxyyphenyl)-1-phenylethyl)phenoxy)phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-5) M in tetrahydrofuran. The antioxidant activities of novel compounds were analyzed through radical scavenging ability of 1,1-dipheny1-2-picrylhydrazyl, chelating ability to ferrous ions and reducing power. In addition to these, the antibacterial activities of compounds were investigated. Moreover, the ground-state geometries of the complexes were optimized using B3LYP/6-31G(d,p) level of density functional theory in order to predict the three-dimensional geometries and electronic structure. (C) 2014 Elsevier B.V. All rights reserved.
Metallo Phthalocyanines Bearing (2-((2 (p-Tolyl)amino)ethoxy) and (2-((2 (p-Tolyl)amino)ethoxy)phthalonitrile Substituents: Synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity
(Elsevier Science Sa, 2014) Celebi, Metin; Agirtas, M. Salih; Okumus, Veysi; Ozdemir, Sadin
The novel phthalonitrile derivatives bearing (2-((2-hydroxyethyl)(p-tolyl)amino)ethoxy) and (2-((2-phenoxyethyl)(p-tolyl)amino)ethoxy)phthalonitrile substituents at peripheral position were prepared by a nucleophilic displacement reaction. Cyclotetramerization of these phthalonitrile derivatives in the presence of corresponding metal salts gave the new metallophthalocyanines. The novel compounds were characterized by using various spectroscopic data. The aggregation investigations carried out in different concentrations indicate that phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-6) M in tetrahydrofuran. In vitro three antioxidant test methods, namely diphenylpicrylhydrazyl radical scavenging activity, metal chelating activity and reducing power were used to determine the antioxidant activity of compounds. Compounds were analyzed for their antibacterial activity against some bacteria by using the disk-diffusion method. (C) 2014 Elsevier B.V. All rights reserved.
Metallo Phthalocyanines Bearing 2-Isopropyl Substituents: Synthesis, Characterization, Aggregation Behavior, Antioxidant and Antibacterial Activity, and Electronic Properties
(Wiley-v C H verlag Gmbh, 2014) Agirtas, M. Salih; Dede, Emrah; Gumus, Selcuk; Dundar, Abdurrahman; Okumus, Veysi
A novel phthalonitrile derivative bearing 2-isopropyl-6-methylpyrimidin-4-yloxy substituents at peripheral positions was synthesized by a nucleophilic substitution reaction. Metallophthalocyanines were obtained from the reaction of the novel phthalonitrile with metal Zn, Cu, Co, and Ni salts. The characterization of the compounds was performed using elemental analysis as well as UV/Vis, FT-IR, and H-1-NMR spectroscopy. The aggregation behaviors of phthalocyanine complexes were also investigated. These metallophthalocyanines do not show any aggregation behavior between 10 (4)-10 (6) M concentration range in THF. The antioxidant activities of the synthesized compounds were evaluated using three different tests: 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, metal chelating activity, and reducing power assays. All the compounds exhibited various antioxidant activities. In addition, antimicrobial activity of the compounds was tested over four gram positive and two gram negative bacteria. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D arrangements and electronic structure.
New Water Soluble Phenoxy Phenyl Diazenyl Benzoic Acid Substituted Phthalocyanine Derivatives: Synthesis, Antioxidant Activities, Atypical Aggregation Behavior and Electronic Properties
(Elsevier Sci Ltd, 2013) Agirtas, M. Salih; Celebi, Metin; Gumus, Selcuk; Ozdemir, Sadin; Okumus, Veysi
Novel substituted phthalonitrile derivatives were obtained by the reaction of 2-(4-hydroxyphenylazo) benzoic acid and 4,5-dichloro-1,2-dicyanobenzene, or 4-nitrophthalonitrile. Peripherally phenoxy phenyl diazenyl benzoic acid substituted zinc (II) phthalocyanine complexes, and their sodium salts were synthesized and characterized for the first time. The newly synthesized phthalocyanine complexes show excellent solubility in water. The aggregation investigations carried out in different concentrations indicate that phenoxy phenyl diazenyl benzoic acid-substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 7.00 x 10(-5)-4.38 x 10(-6) M in DMF. The antioxidant activities of DMF solution of compounds were analyzed through radical scavenging, and chelating ability to Fe2+ cation. Additionally, new compounds did not show any antibacterial activity against some selected bacteria cultures. Moreover, the ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G(d,p) level in order to obtain information about the 3D geometries and electronic structure. (C) 2013 Elsevier Ltd. All rights reserved.
Novel Cobalt(Ii), Zinc(Ii) Phthalocyanines Bearing Discrete Substituents: Synthesis, Characterization, Aggregation Behavior, Electrochemical Properties, and Antioxidant Activity
(Taylor & Francis inc, 2014) Agirtas, M. Salih; Cabir, Beyza; Dundar, Abdurrahman; Okumus, Veysi; Ceyhan, Gokhan
A new phthalonitrile derivative bearing 3,4,5-trimethoxy- benzyloxy and chloro-substituents at peripheral position was prepared by a nucleophilic displacement reaction. Cyclotetramerization of phthalonitrile derivative in dimethylsulfoxide (DMSO) gave the metallophthalocyanines. Novel Co(II), Zn(II) phthalocyanines (Pcs) were obtained from the reaction 4-[(3,4,5-trimethoxybenzyloxy]-5-chlorophthalonitrile and metal salts. The novel compounds have been characterized by using elemental analysis, UV-Vis, FTIR, H-1-NMR spectral data. The aggregation behaviors of Co(II), Zn(II) Pcs were also investigated. These metallophthalocyanines do not show any aggregation behavior between 1.2 x 10(-5) and 4.0 x 10(-6) M concentration range in DMF. The antioxidant activities of Pcs were investigated antioxidant assays such as free radical scavenging ability of 1,1-diphenyl-2-picryl-hydrazyl (DPPH) and ferrous ion chelating ability. Furthermore, the redox properties of the Pcs complexes were investigated by using cyclic voltammetry.
Novel Metal (Ii) Phthalocyanines With 3,4,5-Trimethoxybenzyloxy Synthesis, Characterization, Aggregation Behaviour and Antioxidant Activity
(Elsevier Sci Ltd, 2013) Agirtas, M. Salih; Cabir, Beyza; Ozdemir, Sadin
A new substituted phthalonitrile derivative was prepared by a nucleophilic displacement reaction of 3,4,5-trimethoxybenzyl alcohol with 4-nitrophthalonitrile. Novel metallophthalocyanines IM: Zn (II), Co (II), Ni (II)1 with four peripheral 3,4,5-trimethoxybenzyloxy groups were synthesized by cyclotetramerization of phthalonitrile derivative. These compounds were purified by crystallization and column chromatography. They were characterized by elemental analysis, FTIR, H-1 NMR, C-13 NMR and UV-VIS spectral data. The aggregation investigations carried out in different concentrations indicate that 3,4,5-trimethoxybenzyloxy-substituted phthalocyanine compounds do not have any aggregation behaviour in concentration range of 10(-2)-10(-8) M. The antioxidant activities of phthalocyanines were investigated by in vitro antioxidant assays such as free radical scavenging ability of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and ferrous ion chelating ability. The highest DPPH activity and ferrous ion chelating activity were obtained from Tetrakis [(3,4,5-trimethoxybenzyloxy) phthalocyaninato] cobalt and 4-(3,4,5-trimethoxybenzyloxy) phthalonitrile, respectively. 4-(3,4,5-trimethoxybenzyloxy) phthalonitrile was shown to have a fairly ferrous ion chelating activity. (C) 2012 Elsevier Ltd. All rights reserved.
Study on Dna Binding Properties of Nickle (Ii) Phthalocyanine Compound With 2-Isopropyl Methylphenoxy Substituents
(2017) Arslantaş, Ali; Agirtas, M. Salih
I n this study, previously synthesized Ni (II) phthalocyanine compound bearing 2,10,16,24-tetrakis(2-isopropyl-5-methylphenoxy group was chosen for its interaction with calf thymus-DNA. Calf thymus-DNA was used to determine DNA binding properties of Ni (II) phthalocyanine compound. The DNA binding activities of Ni (II) phthalocyanine compound bearing 2-isopropyl-5-methylphenoxy substituent was investigated by using absorption titration, fluorescence emission, cyclic voltammetry, gel elctrophoresis in Tris-HCl buffer at pH 7.0. In addition to above methods, melting point and viscosity experiment were performed to determine the DNA intercation of the compound in Tris-HCl buffer solution. The results showed that Ni (II) phthalocyanine compound binds strongly to calf thymus-DNA via intercalation binding
Synthesis of Some Metallophthalocyanines Bearing 9-Phenyl Oxy Functional Groups and Investigation of Their Photophysical Properties
(Elsevier Science Bv, 2017) Cabir, Beyza; Agirtas, M. Salih; Duygulu, Ercan; Yuksel, Fatma
As starting material, 4-((9-phenyl-9H-fluoren-9-yl) oxy) phthalonitrile (3) was synthesized and characterized. Cobalt (4), zinc(5), and magnesium(6) phthalocyanines were obtained by reaction of starting material with corresponding metal salt. The new synthesized phthalonitrile derivative (3) was characterized by X-ray crystallography in addition to with other spectroscopic methods. Phthalocyanine complexes were characterized by using electronic absorption, nuclear magnetic resonance spectroscopy, infrared and mass spectra. Furthermore, spectroscopic and photophysical properties such as absorption, excitation, and emission spectra of zinc and magnesium phthalocyanines were investigated in tetrahydrofuran solutions. Of compounds were determined the fluorescence lifetimes and the fluorescence quantum yields. The aggregation behavior for phthalocyanine complexes were carried out in tetrahydrofuran. (C) 2017 Elsevier B.V. All rights reserved.
Synthesis of Some Metallophthalocyanines With Dimethyl 5-(phenoxy) Substituents and Evaluation of Their Antioxidant-Antibacterial Activities
(Pergamon-elsevier Science Ltd, 2015) Agirtas, M. Salih; Karatas, Ceyhun; Ozdemir, Sadin
The synthesis, characterization, spectral, antioxidant and antibacterial properties of dimethyl 5-(phenoxy)-isophthalate substituted Zinc, Cobalt, Copper, and Nickel phthalocyanines are reported. The novel compounds have been characterized by using electronic absorption, nuclear magnetic resonance spectroscopy, infrared, elemental analysis and mass spectrometry. The antioxidant and antibacterial activities of newly synthesized phthalocyanines and its starting material are tested. The DPPH free radical scavenging ability of phthalocyanine Co(II) and Zn(II) complexes on DPPH are 44.8% and 40.1% at 100 mg/L concentration, respectively. The phthalocyanine Co(II) and Cu(II) complexes show very strong ferrous ion chelating activity of 91.2% and 89.3% at concentration of 100 mg/L, respectively. Compound 3 displays strong reducing power like alpha-tocopherol. Antibacterial activities of phthalocyanine Co(II) and Amikacin (30 mu g/disk) against Micrococcus luteus (ATCC 9341) are 16 mm in diameter. (C) 2014 Elsevier B.V. All rights reserved.
Synthesis of Some Novel Phthalocyanines With Methyl 2-(oxy) Substituents, Evaluation of Their Antioxidant- Antibacterial Activities and Electronic Properties
(Wiley-v C H verlag Gmbh, 2015) Agirtas, M. Salih; Karatas, Ceyhun; Gumus, Selcuk; Okumus, Veysi
The synthesis, characterization, spectral, antioxidant, and antibacterial properties of methyl 2-(oxy)-2,2-diphenylacetate substituted metallophthalocyanines (4-7) are reported. A novel phthalonitrile, methyl 2-(2,3-dicyanophenoxy)-2,2-diphenylacetate (3) was prepared and characterized. The new compounds were characterized by using electronic absorption spectroscopy, nuclear magnetic resonance spectroscopy, infrared spectroscopy, and elemental analysis. All compounds were tested for their antioxidant activity by using 2,2-diphenyl-1-picrylhydrazyl radical scavenging ability, metal chelating, and reducing power. Furthermore, these compounds were screened for their in vitro growth inhibiting activity by disc diffusion method against four gram positive and two gram negative bacteria. The electronic data of the new compounds were obtained by computational calculations at B3LYP/6-31G(d,p) level of theory.
Synthesis, Aggregation Behavior, and Electronic Properties of Some Metallophthalocyanines With 2-Isopropyl Substituents
(Wiley-v C H verlag Gmbh, 2015) Agirtas, M. Salih; Karatas, Ceyhun; Gumus, Selcuk
The aim of this study was to perform facile synthesis of novel phthalocyanines with high solubility. The synthesis and characterization of 2-isopropyl-5-methylphenoxy substituted copper, zinc, nickel, and cobalt phthalocyanines are reported. The compounds were characterized by using electronic absorption, nuclear magnetic resonance spectroscopy, infrared and elemental analysis. The aggregation investigations carried out in different concentrations indicate that 2-isopropyl-5-methylphenoxy substituted phthalocyanine complexes do not have any aggregation behavior for the concentration range of 1x10(-5) to 1x10(-6) M in THF. Additionally, the ground-state geometries of the complexes were optimized using density functional theory methods at B3LYP/6-31G (d, p) level in order to obtain information about the 3D geometries and electronic structure.
Synthesis, Characterization, Aggregation Behavior, Antioxidant Activity, and Antibacterial Activity of Metallophthalocyanines Carrying Four Phthalonitriles Group
(Editura Acad Romane, 2016) Guven, M. Emin; Agirtas, M. Salih; Ozdemir, Sadin; Dundar, Abdurrahman
A novel phthalonitrile derivative and zinc (II), cobalt (II), and cupper (II) phthalocyanines complexes were synthesis and characterized. The novel compounds have been characterized by using various spectroscopic data FTIR, UV/vis, NMR, elemental analysis etc. The aggregation investigations carried out in different concentrations indicate that 4- (4-(1-(4-phenoxypheny1)-1-phenylethyl)phenoxy)phthalonitrile substituted phthalocyanine compounds do not have any aggregation behavior for the concentration range of 10(-4)-10(-5) M in tetrahydrofuran. The antioxidant properties of the phthalonitrile and its phthalocyanine compounds were evaluated in three series of in vitro tests: DPPH free radical scavenging, ferrous ion chelating activity and reducing power. Antimicrobial activities of compounds were investigated.
Synthesis, Characterization, and Electrochemical and Electrical Properties of Novel Mono and Ball-Type Metallophthalocyanines With Four 9,9-Bis(4
(Royal Soc Chemistry, 2011) Agirtas, M. Salih; Altindal, Ahmet; Salih, Bekir; Saydam, Sinan; Bekaroglu, Ozer
The new mono-nuclear 4-5 and ball-type homo-dinuclear 6 phthalocyanines have been synthesized from the corresponding phthalodinitrile derivative 3. The synthesized compounds have been characterized by elemental analysis, UV-vis, IR, H-1-NMR and MALDI-TOF-mass spectroscopies. The redox behaviours of the complexes were identified by cyclic voltammetry and square wave voltammetry. The temperature dependence of the electronic properties of compounds and adsorption of SO2 on thin film of 6 were investigated by conductivity measurements using an interdigital transducer structure on glass substrate. Dc conductivity, measured between 300-475 K, is thermally activated with the activation energy ranging between 0.67 and 0.90 eV. The ac conductivity is found to vary with frequency, omega, as omega(s) in which the frequency exponent s decreases with temperature suggesting a hopping conduction mechanism for all compounds. The SO2 sensing result showed that the spin coated film of 6 exhibits very good SO2 sensing properties, fast response and recovery rate, high sensitivity and good repeatability.
Synthesis, Characterization, and Theoretical Studies on Some Metallophthalocyanines With Octakis Phenoxyacetamide Substituents
(Taylor & Francis inc, 2013) Agirtas, M. Salih; Gumus, Selcuk
The synthesis of substituted metallophthalocyanines bearing phenoxyacetamide moieties was achieved by cyclotetramerization of 1,2-bis(phenoxyacetamide)-4,5-dicyanobenzene in the presence of metal (Zn (4), Mg (5), Ni (6)) salts. These compounds were purified by several techniques such as crystallization, column chromatography, and wash with different solvents. The new compounds were characterized by elemental analysis, IR, 1H-NMR, and UV-Vis spectral data. The ground-state geometries of the complexes were optimized using density functional theory (DFT) methods at B3LYP/6-31G (d, p) level. The results of thermal analysis of novel phthalocyanines 46 have also been reported herein.