An effect of the substituent position and metal type on the electropolymerization properties of chalcone substituted metallophthalocyanines

Biyiklioglu, Zekeriya/0000-0001-5138-214XWOS: 000365921800013PubMed: 26551392Cobalt(II) and manganese(III) phthalocyanines bearing peripherally and non-peripherally tetra substituted {(2E)-3-[4-(dimethylamino) phenyl]prop-2-enoyl} phenoxy groups were synthesized by cyclotetramerization of the phthalonitrile derivatives and their electrochemical properties were examined using CV and SWV techniques for the first time. The novel compounds were characterized by using IR, H-1-NMR, C-13-NMR, UV-Vis and MS spectral data. Cyclic and square wave voltammetry revealed well-defined metal-based and ligand-based reduction processes within the complexes. Electrochemical measurements exhibit that all complexes oxidatively electropolymerized on the Pt working electrode during repetitive cyclic voltammetry measurements. This study is the first example of electropolymerization of peripherally and non-peripherally tetra chalcone substituted cobalt(II) and manganese(III) phthalocyanines. The types of the metal centers of the complexes and the position of substituents affect the character of the polymerization processes.Research Fund of Karadeniz Technical University, Trabzon, TurkeyKaradeniz Teknik University [9670]This study was supported by the Research Fund of Karadeniz Technical University (Project no. 9670), Trabzon, Turkey

Synthesis and acetylcholinesterase enzyme inhibition properties of axially disubstituted silicon phthalocyanines and their quaternized derivatives

In this paper, axial 1,3-bis[4-(4-acetylpiperazin-1-yl)phenoxy]propanoxy and {2-[4-(4-acetylpiperazin-1-yl)phenoxy]ethoxy}ethoxy groups substituted silicon(IV) phthalocyanines ( PP-D-Si, PP-OH2-Si) and their quaternized derivatives (PP-D-SiQ, PP-OH2-SiQ) were synthesized and characterized. The acetyl -cholinesterase inhibition values of 1,3-bis[4-(4-acetylpiperazin-1-yl)phenoxy]propanoxy and {2-[4-(4-acetylpiperazin-1-yl)phenoxy]ethoxy}ethoxy groups substituted silicon(IV) phthalocyanines ( PP-D-Si, PP-OH2-Si) and their quaternized derivatives (PP-D-SiQ, PP-OH2-SiQ) were measured by IC50 that reduces enzyme activity to 50% refers to the concentration of inhibitor. The synthesis compounds were classified as silicon and their quaternized derivatives and tagged as PP-D-Si, PP-OH2-Si, PP-D-SiQ and PP-OH2-SiQ. Except for the result of PP-D-SiQ was 1.586 & PLUSMN; 0.129 mu M, the results were expressed as mM ranged between 0.553 and 3.626 mM. (c) 2022 Published by Elsevier B.V.Research Fund of Karadeniz Technical University 876

The synthesis and characterization of a porphyrazine bearing aza-15-crown-5 moieties in the peripheral positions and its cobalt(II) complex

Biyiklioglu, Zekeriya/0000-0001-5138-214XWOS: 000253205200007The synthesis of novel metal-free (H-2-Pz) and metalloporphyrazines (MgPz and CoPz), peripherally substituted with eight aza-15-crown-5 moieties, is described. The novel compounds were characterized by elemental analysis, i.r, H-1 and C-13-n.m.r, UV-vis and m.s. spectral data

Design, synthesis and biological evaluation of water soluble and non-aggregated silicon phthalocyanines, naphthalocyanines against A549, SNU-398, SK-MEL128, DU-145, BT-20 and HFC cell lines as potential anticancer agents

Cancer has become an important public problem in worldwide since cancer incidence and mortality are growing rapidly. In this study, water soluble and non-aggregated silicon (IV) phthalocyanines and naphthalocyanines containing (3,5-bis{3-[3-(diethylamino)phenoxy]propoxy}phenyl)methoxy groups have been synthesized and characterized to investigate their anticancer potential. Their DNA binding/nuclease, topoisomerases inhibition were investigated using UV-Vis absorption, thermal denaturation and agarose gel electrophoresis. The in vitro cytotoxic properties of the compounds on human lung (A549), breast (BT-20), liver (SNU-398), prostate (DU-145), melanoma (SK-Mel 128) carcinoma and human fibroblast (HFC) normal cell lines were evaluated by using MTT assay. In order to determine the mechanism of cancer cell growth suppression, cell cycle analysis was carried out using flow cytometer on A549 cell line. The Kb values of SiPc1a and SiNc2a were 6.85 +/- (0.35) x 10(6) and 1.72 +/- (0.16) x 10(4) M-1 and T-m values of ct-DNA were calculated as 82.02 degrees C and 78.07 degrees C, respectively in the presence of both compounds. The Delta(Tm), values of SiPc1a and SiNc2a were calculated as 6.45 and 2.50 degrees C, respectively. The nuclease effects of SiPc1a and SiNc2a with supercoiled plasmid pBR322 DNA demonstrated that both compounds did not trigger any DNA nuclease effects at the lowest concentrations without irradiation whereas both compounds in the presence of activating agent (H2O2) showed significant plasmid DNA nuclease actions under irradiation (22.5 J/cm(2)). SiPc1a and SiNc2a inhibited to topoisomerase I on increasing concentrations whilst they had lower inhibition action toward topoisomerase II that of topoisomerase I. The in vitro cytotoxicity studies displayed that SiPc1a had the highest cytotoxic effects among the tested compounds against A549, SNU-398, SK-MEL128, DU-145, BT-20 and HFC cell lines with CC50 values ranged from 0.49 to 2.99 mu M. Furthermore, SiPc1a inhibited cell proliferation by cell cycle arrest in G(0)/G(1) phase. All of these results suggested that SiPcla is a promising candidate as an anticancer agent

The synthesis and characterization of a new (E,E)-dioxime containing 18-membered dithiadiazadioxamacrocyclic moieties and its mononuclear complexes

Biyiklioglu, Zekeriya/0000-0001-5138-214XWOS: 000253205200003A new (E,E)-dioxime, (21Z,22Z)-6,7,9,10,12,13-hexahydro-16H- benzo[h][1,4,7,16,10,13][1, 4,7,16,10,13]dioxadithiadiazacyclooctadecine-21,22(20H,23H)-dione dioxime (H (2) L) has been synthesized by reacting cyanogen-di-N-oxide (2) with (2-{[2-(2-{2-[(7-aminocyclohepta-1,4,6-trien-1-yl)thio]ethoxy}ethoxy)ethyl]thio}phenyl)amine. Mononuclear complexes of this ligand have been synthesized by reacting the vic-dioxime (H2L) with CuCl2, NiCl2.6H(2)O and CoCl2.6H(2)O respectively. The BF2+ capped Ni(II) and Co(III) complexes of the dioxime have been synthesized from. The new compounds were characterized by a combination of elemental analysis, H-1- and C-13-n.m.r, I.R. and m.s. spectral data

Synthesis of water-soluble BODIPY dyes and investigation of their DNA interaction properties and cytotoxicity/phototoxicity

In this study, water-soluble BODIPY dyes (BDPY-4, BDPY-5) bearing dimethylamino and diethylamino groups were synthesized for the first time. The DNA interaction and nuclease effect of two water-soluble BODIPY dyes were examined using absorption, competitive binding experiments, and agarose gel electrophoresis. Then, cytotoxicity and phototoxicity of the compounds were determined against A549 cells by MTT cell viability assay. The ultraviolet-visible (UV-vis) spectra of BDPY-4 and BDPY-5 displayed hypochromism and absorption maxima shifted to the red region. In addition, K-b values of the compounds were calculated as 2.23 x 10(4) and 4.84 x 10(4) M-1, respectively. An high-performance liquid chromatography (HPLC) instrument without a column was used to conduct competitive binding experiments for the first time. The approach prevented the decrease in the response due to dilution and enabled the analysis to be carried out in a short time. Upon increasing concentrations of the compounds, the emission intensity of EB-DNA significantly decreased. These obtained results suggested that the compounds bound to CT-DNA with intercalative mode. At the same time, the Stern-Volmer constants were determined as 1.80 x 10(6) and 1.79 x 10(6) M-1 for BDPY-4 and BDPY-5, respectively, which is coherent with intercalative binding mode. The compounds did not display noticeable photonuclease actions with light irradiation. BDPY-4 and BDPY-5 showed moderate phototoxic properties on light irradiation

Triazole substituted metal-free, metallo-phthalocyanines and their water soluble derivatives as potential cholinesterases inhibitors: Design, synthesis and in vitro inhibition study

4th Symposium on Biotransformations for Pharmaceutical and Cosmetic Industry -- JUN 25-27, 2018 -- Trzebnica, POLANDKELES, TURGUT/0000-0002-1911-8020; Biyiklioglu, Zekeriya/0000-0001-5138-214XWOS: 000479184600057PubMed: 31288136In this study, 1,2,3-triazole substituted metal-free and metallo phthalocyanines (4, 5, 6) and their water soluble derivatives (4a, 5a, 6a) were designed, synthesized for the first time and tested in vitro on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Most phthalocyanines exhibited good inhibitory activities on these enzymes. Among the six phthalocyanines and starting compounds, 4a showed the most interesting profile as a submicromolar selective inhibitor of AChE (IC50 = 0.040 mu M) and 5a showed the most effective inhibitor of BChE (IC50 = 0.1198 mu M).Scientific and Technological Research Council of Turkey, Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [116R054]This study was supported by The Scientific and Technological Research Council of Turkey, Turkey (TUBITAK, Grant No. 116R054)

Synthesis and in vitro alpha-glucosidase and cholinesterases inhibitory actions of watersoluble metallophthalocyanines bearing ({6-[3-(diethylamino)phenoxy]hexyl}oxy groups

In this paper, we have prepared peripherally tetra-({6-[3-(diethylamino)phenoxy]hexyl}oxy substituted cobalt(II), copper(II), manganese(III) phthalocyanines (3, 4, 5) and their water-soluble derivatives (3a, 4a, 5a). Then, in vitro alpha-glucosidase and cholinesterases inhibitory actions of the water-soluble 3a, 4a, 5a were examined using spectrophotometric methods. 4a had the highest inhibitory effects among the tested compounds against alpha-glucosidase due to IC50 values. 4a and 5a had 40 fold higher inhibitory effects than the positive control. For cholinesterases, the compounds showed significant inhibitory actions that of galantamine which was used as a positive control. According to the SI value, 3a inhibited acetylcholinesterase enzyme selectively. In kinetic studies, 4a was a mixed inhibitor for alpha-glucosidase, 3a was a competitive inhibitor for AChE, and 4a was a mixed inhibitor for BuChE. The therapeutic potential of these compounds has been demonstrated by in vitro studies, but these data should be supported by further studies

Design, synthesis, characterization of peripherally tetra-pyridine-triazole-substituted phthalocyanines and their inhibitory effects on cholinesterases (AChE/BChE) and carbonic anhydrases (hCA I, II and IX)

Biyiklioglu, Zekeriya/0000-0001-5138-214XWOS: 000507637400021PubMed: 31808483In this study, phthalocyanine precursors (5 and 9) and 1,2,3-triazole-substituted metal-free and metallo phthalocyanines (9a-c) were designed and synthesized for the first time and evaluated in vitro for key molecular targets. The structures of the novel compounds were characterized via FT-IR, H-1/C-13 NMR, UV-Vis, and mass spectroscopy. The inhibitory activities of the compounds were tested against human carbonic anhydrase isoforms hCA I, II (cytosolic, ubiquitous isozymes), and IX (transmembrane, cancer-associated isozyme) and cholinesterases (AChE and BChE, which are associated with Alzheimer's disease). Among the three phthalocyanines and starting compounds, 9b showed the most interesting profile as a nanomolar selective inhibitor of hCA I (K-i = 37.2 nM) and 9c showed the most effective inhibitory effect on hCA II, IX, AChE and BChE (K-i = 41.9, 27.4, 5.8 and 45.8 nM, respectively). This study is also the first example of cancer-associated isozyme hCA IX inhibition by phthalocyanines.Scientific and Technological Research Council of Turkey (TUBITAK)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [116R054]This study was supported by The Scientific and Technological Research Council of Turkey (TUBITAK, Grant No. 116R054)

Dye-sensitized solar cells based on zinc(II) phthalocyanines bearing 3-pyridin-3-ylpropoxy anchoring groups

Guzel, Emre/0000-0002-1142-3936WOS: 000582442100001In this study, nonperipherally tetra-substituted (2), peripherally tetra-substituted (3), and peripherally octa-substituted (4) zinc(II) phthalocyanines were synthesized as sensitizers for dye-sensitized solar cells (DSSCs) in which 3-pyridin-3-ylpropoxy substituent acts as anchoring unit to bind TiO2 surface. the optical results indicated that there is an interaction between the dyes and the TiO2 surface. the photovoltaic performances of the DSSCs based on these dyes were found to depend on both the position and number of the substituents. Despite the more red-shifted absorption, the DSSC based on 2 showed the conversion efficiency of 0.68%, which is lower than 1.36% and 0.92% for 3 and 4, respectively, under one sun (AM 1.5G). the vertical orientation of the dye on TiO2 surface could be the main reason for the higher photovoltaic performance of complex 3, which is beneficial for not only injecting the electrons into the conduction band of TiO2 but also reducing the charge recombination. Overall, these results demonstrate that the peripherally tetra-substituted 3-pyridin-3-ylpropoxy zinc(II) phthalocyanine complex (3) as a sensitizer can more efficiently utilize the photons in the red/near-infrared region with respect to the other complexes studied