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    Novel and effective peripheral tetra-substituted phthalocyanines with quinazoline groups for cancer treatment: synthesis, photophysical and photochemical properties, and in-vitro studies
    (Elsevier Science Sa, 2024) Gulec, Ozcan; Bilgicli, Ahmet T.; Hepokur, Ceylan; Gunsel, Armagan; Arslan, Mustafa; Yarasir, M. Nilufer
    Within the scope of this study, starting from 3,4-dihydronaphthalen-1(2H)-one (1), 4-(2-amino-5,6-dihydrobenzo[h]quinazolin-4-yl)phenol (3) was synthesized in two stages according to literature. In the second step, 4-(4-(2-amino-5,6-dihydrobenzo[h]quinazolin-4-yl)phenoxy)phthalonitrile (4) was prepared as the starting ligand compound with the help of this substance for the first time. Then, novel metallophthalocyanine derivatives [2(3), 9(10), 16(17), 23(24)-Tetrakis[4-(2-amino-5,6-dihydrobenzo[h]quinazolin-4-yl)phenol] phthalocyaninato zinc(II) (5), copper (II) (6), cobalt (II) (7)] were synthesized in the presence of suitable metal salts. The structure of synthesized procersur and novel compounds were elucidated by convenient spectroscopic methods. The effect on solubility and aggregation behaviors substitution with 4-(2-amino-5,6-dihydrobenzo[h] quinazolin-4-yl)phenol from the peripheral position was investigated. The newly synthesized tetra -substituted phthalocyanines (5-7) show good solubility in common organic solvents. Also, they have no aggregation tendency between 1 and 10 mu M concentrations. In addition, the photophysical and photochemical properties of substituted phthalocyanines were examined. The ability to produce 1O2 of compound (5) was 0.79 in DMSO and 0.75 in THF media. Finally, the cytotoxicity effects of the synthesized phthalonitrile (4) and its metallophthalocyanines (5-7) on MCF 7, MDA-MB-231, HT -29, C6, AGS and L-929 cells were determined by XTT (2,3bis(2-methoxy-4-nitro-5-sulfophenyl)-5-[(phenylamino)carbonyl] 2H-tetrazolium hydroxide) method. The obtained data were compared with standard cell lines.
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    Peripheral (E)-2-[(4-hydroxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one)]-coordinated phthalocyanines with improved enzyme inhibition properties and photophysicochemical behaviors
    (Wiley-V C H Verlag Gmbh, 2024) Gulec, Ozcan; Bilgicli, Ahmet T.; Tuzun, Burak; Taslimi, Parham; Gunsel, Armagan; Gulcin, Ilhami; Arslan, Mustafa
    In this study, (E)-4-{4-[(1-oxo-3,4-dihydronaphthalen-2(1H)-ylidene)methyl]phenoxy}phthalonitrile (4) and its phthalocyanine derivatives (5-8) were synthesized for the first time. Aggregation behaviors of the novel soluble phthalocyanines in organic solvents were investigated. In addition, the efficiency of O-1(2) production of (5) and ZnPc (6) was investigated. The singlet oxygen quantum yields (Phi(Delta)) for 2HPc (5) and ZnPc (6) were found to be 0.58 and 0.83, respectively. Additionally, novel phthalocyanines (5-8) were investigated for their ability to inhibit enzymes. They exhibited a highly potent inhibition effect on human carbonic anhydrase I and II (hCA I and II) and alpha-glycosidase (alpha-Gly) enzymes. K-i values are in the range of 2.60 +/- 9.87 to 11.53 +/- 6.92 mu M, 3.35 +/- 0.53 to 15.47 +/- 1.20 mu M, and 28.60 +/- 4.82 to 40.58 +/- 7.37 nM, respectively. The calculations of the studied molecule at the B3LYP, HF, and M062X levels in the 6-31G basis sets were made using the Gaussian package program. Afterward, the interactions occurring in the docking calculation against a protein that is the crystal structure of hCA I (PDB ID: 2CAB), the crystal structure of hCA II (PDB ID: 5AML), and the crystal structure of alpha-Gly (PDB ID: 1R47), were examined. Following that, Protein-Ligand Interaction Profiler (PLIP) analysis was used to look at the interactions that occurred during the docking calculation in further detail.