Assessing cytotoxic activities, theoretical and in silico molecular docking calculations of phthalocyanines bearing cinnamyloxy-groups.

Cancer has been recognized as one of the deadliest diseases in the world in recent years. By chemically tailoring specific properties, anticancer agents can be prepared very effectively for the treatment of various cancer types. In this manner, as anticancer agents, a series of soluble metal-free and metallophthalocyanines carrying cinnamyloxy-groups at peripheral ß-positions have been prepared. All synthesized phthalocyanines were characterized by various spectroscopic approaches such as ultraviolet - visible (UV - Vis), Fourier transform infrared (FT-IR), and matrix-assisted laser deionization/ionization time-of-flight mass spectroscopy (MALDI-TOF MS) techniques. These compounds are highly soluble in dimethyl sulfoxide (DMSO) and soluble in common organic solvents. The spectroscopic properties, cytotoxicity, and theoretical calculations of these complexes have been investigated. In cytotoxicity tests, compounds 1, 4, and 7 are the most active against HT-29 cell lines with IC50 values of 36.9 µM, 32.5 µM, and 51.1 µM, respectively. Also, the most and the least cytotoxic compounds against healthy CCD cell line is compounds 5 and 6 with the IC50 value of 13.4 µM and >250 µM, respectively. The PDB ID:4BQG target protein representing the HT-29 cancer cell line and the anti-cancer activities of phthalonitrile and its phthalocyanines were supported by molecular docking studies. Density Functional Theory (DFT) study supported the experimental results, including the spectral data, and implied that the compounds 5-7 are comparable by their characteristics, such as electronic properties, optical properties, electrostatic potentials, reactivity parameters, with the earlier studied compounds 2-4, which were successfully proved to be good candidates for cancer treatment.Communicated by Ramaswamy H. Sarma.

In Silico and In Vitro Studies of Novel Azomethines on DNA Repair Genes in Gastric Cell Lines.

We herein report the determination of the cytotoxic activity and expression profiles of some DNA repair genes of newly synthesized azomethines in the gastric cancer cell line (AGS). The studied novel compounds were synthesized by a condensation reaction and received compounds were characterized by 1H and 13C NMR spectroscopy methods. Furthermore, they were applied to the AGS cell line at eight different concentrations (0.1-50 µg/mL). Anticancer activities were determined using the MTT method. Expression levels of ATR, ERCC1, TOP2A, and ABCB1 genes were determined by the RT-PCR method. Biochemical parameters were also examined. The interaction of proteins with other proteins was investigated with the String v11 program. The IC50 values of compounds 1, 2, and 3 obtained after 72 h were 23.10, 8.93, and 1.58 µg/mL, respectively. The results demonstrate that the cytotoxic activity of compound 3 on AGS cancer cells is higher in comparison with other molecules. It was determined that the expression levels of ATR, TOP2A, and ABCB1 genes in compounds 1, 2, and 3 were decreased compared to the control group. In addition, it was determined that ERCC1 gene expression increased in compound 3, decreased in compound 2, and remained unchanged in compound 1 (p < 0.001). In AGS gastric cancer cells, a 64% decrease was detected for GST levels in compound 1, while a 38% decrease in GSH levels in compound 2. In addition, compounds 1-3 were examined at the molecular level with computational techniques and the docking studies revealed 4LN0 as a target protein.

Synthesis, docking studies, in vitro cytotoxicity evaluation and DNA damage mechanism of new tyrosine-based tripeptides.

Peptides are one of the leading groups of compounds that have been the subject of a great deal of biological research and still continue to attract researchers' attention. In this study, a series of tripeptides based on tyrosine amino acids were synthesized by the triazine method. The cytotoxicity properties of all compounds against human cancer cell lines (MCF-7), ovarian (A2780), prostate (PC-3), and colon cancer cell lines (Caco-2) were determined by the 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide assay method, and % cell viability and logIC50 values of the compounds were calculated. Significant decreases in cell viability were observed in all cells (p < 0.05). The comet assay method was used to understand that the compounds that showed a significant decrease in cell viability had this effect through DNA damage. Most of the compounds exhibited cytotoxicity by DNA damage mechanism. Besides, their interactions between investigated molecule groups with PDB ID: 3VHE, 3C0R, 2ZCL, and 2HQ6 target proteins corresponding to cancer cell lines, respectively, were investigated by docking studies. Finally, molecules with high biological activity against biological receptors were determined by ADME analysis.

Spectroscopic, crystal structure and DFT-assisted studies of some nickel(II) chelates of a heterocyclic-based NNO donor aroylhydrazone: in vitro DNA binding and docking studies.

Five new nickel(II) complexes have been synthesised with an NNO donor tridentate aroylhydrazone (HFPB) employing the chloride, nitrate, acetate and perchlorate salts, and all the complexes are physiochemically characterized. Elemental analyses suggested stoichiometries as Ni(FPB)(NO3)]·2H2O (1), [Ni(HFPB)(FPB)]Cl (2), [Ni(FPB)(OAc)(DMF)] (3), [Ni(FPB)(ClO4)]·DMF (4), [Ni(FPB)2] (5). Aroylhydrazone is found coordinating in deprotonated iminolate form in four of the complexes (1, 3, 4, 5) however in one case (complex 2), two aroylhydrazone moieties are binding to the metal centre in the neutral and anionic forms. The structure of the bisligated complex 5, found using single crystal X ray diffraction studies confirmed that the metal has a distorted octahedral N4O2 coordination environment, with each of the two deprotonated ligands coordinating through the pyridine nitrogen, imino-hydrazone nitrogen and the enolate oxygen of the hydrazone moiety. To compare and study, the electronic interactions and stabilities of the metal complexes, various quantum chemical parameters were calculated. Moreover, Hirshfeld surface analysis was carried out for complex 5 to determine the intermolecular interactions. The biophysical attributes of the ligand and complex 5 have been investigated with CT-DNA and experimental outcomes show that the Ni(II) complex exhibited higher binding propensity towards DNA as compared to ligand. Furthermore, to specifically understand the type of interactions of the metal complexes with DNA, molecular docking studies were effectuated. In addition, the electronic and related reactivity behaviors of the ligand and five Ni(II) complexes were studied using B3LYP/6-31 + + G**/LANL2DZ level. As expected, the obtained results from Natural Bond Orbital (NBO) computations displayed that the resonance interactions (n → π* and π → π*) play a determinant role in evaluating the chemical attributes of the reported compounds.

A series of phenanthroline-imine compounds: Computational, OLED properties and fluorimetric sensing of nitroaromatic compounds.

In this study, Schiff base compounds (1-5) were synthesized by the reaction of 5-amino-1,10-phenanthroline with various aldehydes. The molecular structures of the synthesized compounds were characterized by FT-IR, 1H/13C NMR and mass spectroscopic methods. Single crystals of 1 were obtained and their molecular structures in crystalline form were determined by single crystal X-ray diffraction study. The sensor properties of the synthesized compounds against nitroaromatic compounds [nitrobenzene (NB), 4-nitrophenol (NP), 2,4-dintrophenol (DNP) and 1,3,5-trinitrophenol (TNP)] were investigated by fluorescence spectroscopy. Compound 3 have highest sensitivity for the sensing of 1,3,5-trinitrophenol (TNP) (Ksv: 4.63 × 104 M-1) with LOD of 4.01 µM while compound 5 showed the highest sensitivity for 2,4-dinitrophenol (DNP) (Ksv: 5.71 × 104 M-1) with LOD of 4.75 µM. In addition, the structural parameters (bond angles/lengths), contour diagrams of HOMO/LUMO molecular orbitals, molecular electrostatic potential (MEP) maps, non-linear optical (NLO) and OLED properties were investigated by computational studies. According to the HOMO and LUMO energies, the NLO property of the molecule (5) is higher than both other molecules and the reference substance urea.

Bromination and conversion of tetrahydro-1H-indene to bisoxirane with a new approach: synthesis, structural characterization by spectroscopic and theoretical methods, and biological analysis supported by DFT and docking.

In this study, a new method for synthesizing diepoxides is proposed. Tetrahydroindene 1 was brominated with NBS in the presence of LiClO4 and acetic acid, resulting in the formation of dibromodiacetate derivatives 2 and 3. Treatment of compounds 2 and 3 with NaOH in methanol produced a mixture of diepoxides 4 and 5. Additionally, direct bromination of tetrahydro-1H-indene yielded tetrabromo octahydroindene isomers 6 and 7. The structures of the compounds were characterized using spectroscopic techniques such as 1H NMR, 13C NMR, APT, COSY, and XRD. The new method provides an easy and selective route to access epoxides for the synthesis of various chemicals. This study also highlights the selective formation of endo-exo and exo-exo orientations of the obtained diepoxides, distinguishing it from previous studies. The stability and properties of the stereoisomers were investigated using computational methods, revealing the most stable configurations. Reactive sites in the molecules were identified using contour diagrams and molecular electrostatic potential maps. The anticancer properties of the compounds were evaluated in silico, comparing them to 5-fluorouracil (5-FU) against several cancer cell lines. The compounds exhibited the most effective anticancer activity against MCF-7 cells, with the order of anticancer activities generally determined as 2 > 7 > 3 > 6 > 5 > 4 > 5-FU.

Synthesis of New Cinnamoyl-Amino Acid Conjugates and in Vitro Cytotoxicity and Genotoxicity Studies.

Amino acid conjugates are described by the reaction of amino acids with bioactive organic groups such as vitamins, hormones, flavonoids, steroids, and sugars. In this study, 12 new conjugates were synthesized by reaction of cinnamic acid derivatives with various amino acids. Cytotoxic studies against four different human cancer cells (MCF7, PC-3, Caco-2, and A2780) were carried out by MTT assay method at five different concentrations. The structure-activity relationships based on the cell viability rates were evaluated. To compare the anticancer activities of the compounds using computational chemistry methods, they were docked against A2780 human ovarian cancer, Michigan Cancer Foundation-7 (MCF7), human prostate cancer (PC-3) and human colon epidermal adenocarcinoma (Caco-2) cell lines and compared with the standard 5-Fluorouracil. The results indicate that the efficacy of cinnamic acid derivatives increases with the presence of amino acids. Comet assay was conducted to understand whether the cell deaths occur through DNA damage mechanism and the results exhibit that the changes in the specified parameters were statistically significant (p<0.05). Our study demonstrated that the compounds cause cell death through the formation of DNA damage mechanism.

Potential thiosemicarbazone-based enzyme inhibitors: Assessment of antiproliferative activity, metabolic enzyme inhibition properties, and molecular docking calculations.

A new series of thiosemicarbazone derivatives (1-11) were prepared from various aldehydes and isocyanates with high yields and practical methods. The structures of these compounds were elucidated by Fourier transform infrared, 1 H-nuclear magnetic resonance (NMR), 13 C-NMR spectroscopic methods and elemental analysis. Cytotoxic effects of target compounds were determined by 2,3-bis-(2-methoxy-4-nitro-5-sulfophenyl)-2H-tetrazolium-5-carboxanilide assay and compound 1 showed significant cytotoxic activity against both MCF-7 and MDA-MB-231 cells, with half-maximal inhibitory concentration values of 2.97 µM and 6.57 µM, respectively. Moreover, in this study, the anticholinergic and antidiabetic potentials of these compounds were investigated. To this aim, the effect of the newly synthesized thiosemicarbazone derivatives on the activities of acetylcholinesterase (AChE) and αglycosidase (α-Gly) was evaluated spectrophotometrically. The title compounds demonstrated high inhibitory activities compared to standard inhibitors with Ki values in the range of 122.15-333.61 nM for α-Gly (Ki value for standard inhibitor = 75.48 nM), 1.93-12.36 nM for AChE (Ki value for standard inhibitor = 17.45 nM). Antiproliferative activity and enzyme inhibition at the molecular level were performed molecular docking studies for thiosemicarbazone derivatives. 1M17, 5FI2, and 4EY6, 4J5T target proteins with protein data bank identification with (1-11) compounds were docked for anticancer and enzyme inhibition, respectively.

Synthesis, photophysical, electrochemical, and DFT examinations of two new organic dye molecules based on phenothiazine and dibenzofuran.

New dyes were developed and produced utilizing distinct electron donors (phenothiazine and dibenzofuran), a π-spacer, and an electron acceptor of cyanoacetohydrazide, and their structures were studied using FT-IR and NMR spectroscopy. Following the synthesis of dye molecules, the photophysical and photovoltaic characteristics were investigated using experimental and theoretical methods. The photosensitizers have been exposed to electrochemical and optical property experiments in order to study their absorption performance and also molecular orbital energies. The monochromatic optical conversion efficiency of (Z)-N-((5-(10H-phenothiazin-2-yl)furan-2-yl)methylene)-2-cyanoacetohydrazide (PFCH) was found higher than that of (Z)-2-cyano-N'-((5-(dibenzo[b,d]furan-4-yl)furan-2-yl)methylene)acetohydrazide (BFCH), with IPCEs of 58 and 64% for BFCH and PFCH, respectively. According to the photosensitizer molecular energy level diagram, the studied dye molecules have strong thermodynamically advantageous ground and excited-state oxidation potentials for electron injection into the conduction band of titanium oxide. It was observed that the ability to attract electrons correlated favorably with molecular orbital energy. While density functional theory calculations were used to examine molecule geometries, vertical electronic excitations, and frontier molecular orbitals, experimental and computed results were consistent. Natural bond orbital and nonlinear optical properties were also calculated and discussed.

Phthalocyanine complexes with (4-isopropylbenzyl)oxy substituents: preparation and evaluation of anti-carbonic anhydrase, anticholinesterase enzymes and molecular docking studies.

In this study, the preparation, aggregation behavior and investigation of carbonic anhydrase and cholinesterase enzyme inhibition features of non-peripherally (4-isopropylbenzyl)oxy-substituted phthalocyanines (4-6) are reported for the first time. The chemical structures of these new phthalocyanines were elucidated by UV-Vis (ultraviolet-visible), FT-IR (Fourier transform infrared spectrometry), NMR (nuclear magnetic resonance) and MALDI-TOF (matrix-assisted laser desorption/ionization time-of-flight) mass spectrometry. The substitution of 4-isopropylbenzyl)oxy groups benefits a remarkable solubility and redshift of the phthalocyanines Q-band. Also, these complexes were tested against some enzymes such as butyrylcholinesterase enzyme, human carbonic anhydrase I and II isoforms and acetylcholinesterase enzyme. The phthalocyanine complexes showed Ki values of in the range of 478.13 ± 57.25-887.25 ± 101.20 µM against hCA I, 525.16 ± 45.87-921.14 ± 81.25 µM against hCA II, 68.33 ± 9.13-201.15 ± 35.86 µM against AChE and 86.25 ± 13.65-237.54 ± 24.7 µM against BChE. Molecular docking studies were performed to investigate the binding modes and interaction energies of the (2-6) complexes with the hCA I (PDB ID:1BMZ), hCA II (PDB ID:2ABE), AChE (PDB ID:4EY6) and BChE (PDB ID:2PM8).

N-substituted benzenesulfonamide compounds: DNA binding properties and molecular docking studies.

Benzenesulfonamide-based imine compounds 5-8 were prepared and screened for their binding properties to the FSdsDNA. The structures of synthesized compounds were elucidated by the spectroscopic and analytical methods. Compounds 5-8 were screened for their interactions with the FSdsDNA. Compound 8 showed the highest binding affinity to the FSdsDNA with intrinsic binding constant of 3.10 × 104 M-1. The compounds caused the quenching of the DNA-EB emission indicating displacement of EB (ethidium bromide) from the FSdsDNA. Finally, the binding interactions between the DNA and binder molecules 5-8 were examined by the molecular docking studies. The compounds locate approximately same region of the minor groove of DNA via hydrogen bonding contacts between the sulfonamide oxygen atoms and the DG10/DG16 nucleotides of DNA.Communicated by Ramaswamy H. Sarma.

Biologically active phthalocyanine metal complexes: Preparation, evaluation of α-glycosidase and anticholinesterase enzyme inhibition activities, and molecular docking studies.

In this study, preparation, as well as investigation of α-glycosidase and cholinesterase (ChE) enzyme inhibition activities of furan-2-ylmethoxy-substituted compounds 1-7, are reported. Peripherally, tetra-substituted copper and manganese phthalocyanines (5 and 6) were synthesized for the first time. The substitution of furan-2-ylmethoxy groups provides remarkable solubility to the complex and redshift of the phthalocyanines Q-band. Besides, the inhibitory effects of these compounds on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glycosidase (α-Gly) enzymes have been investigated. The AChE was inhibited by these compounds (1-7) in low micromolar levels, and K i values were recorded between 11.17 ± 1.03 and 83.28 ± 11.08 µM. Against the BChE, the compounds demonstrated K i values from 7.55 ± 0.98 to 81.35 ± 12.80 µM. Also, these compounds (1-7) effectively inhibited α-glycosidase, with K i values in the range of 744.87 ± 67.33 to 1094.38 ± 88.91 µM. For α-glycosidase, the most effective K i values of phthalocyanines 3 and 6 were with K i values of 744.87 ± 67.33 and 880.36 ± 56.77 µM, respectively. Moreover, the studied metal complexes were docked with target proteins PDB ID: 4PQE, 1P0I, and 3WY1. Pharmacokinetic parameters and secondary chemical interactions that play an active role in interaction were predicted with docking simulation results. Overall, furan-2-ylmethoxy-substituted phthalocyanines can be considered as potential agents for the treatment of Alzheimer's diseases and diabetes mellitus.

Computational investigation of molecular structures, spectroscopic properties and antitumor-antibacterial activities of some Schiff bases.

Molecular structures, spectroscopic properties (IR, 1H NMR and 13C NMR, UV-VIS), molecular electrostatic potential maps and some molecular properties (ionization energy, electron affinity, energy gap, hardness, electronegativity, electrophilicity index, static dipole moment and average linear polarizability) of three Schiff bases which are 2-((ethylamino)methyl)-6-methoxyphenol (HL1), 2-((ethylamino) methyl)-6-methylphenol (HL2) and 2-((ethylamino)methyl)-6-chlorophenol (HL3) were computed at B3LYP/6-31G(d) level in aqueous phase. The effects of methoxy, methyl and chloro substituents on Schiff bases were examined and it was found that the electron donating property of methyl and chlorine substituents was higher than the methoxy substituent. In order to investigate the antitumor activities of Schiff bases were docked against the breast cancer (MCF7) cell line. Molecular docking results were compared with antitumor standard 5-fluorouracil. Antitumor activity of HL2 and HL3 molecule was found to be higher than HL1 against MCF-7 cell line. In addition, in order to predict the antibacterial activities of Schiff bases were docked against the Mycobacterium tuberculosis (H37Rv) cell line. Docking results were compared with the antibacterial reference N-(salicylidene)-2-hydroxyaniline. Antibacterial activity of HL2 and HL3 molecules was found to be higher than HL1. It is estimated that the binding of the electron donating group to the ortho position of the hydroxyl group in studied Schiff bases increases both antitumor and antibacterial activity.

Quinoline-based promising anticancer and antibacterial agents, and some metabolic enzyme inhibitors.

A series of substituted quinolines was screened for their antiproliferative, cytotoxic, antibacterial activities, DNA/protein binding affinity, and anticholinergic properties by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide cell proliferation, lactate dehydrogenase cytotoxicity, and microdilution assays, the Wolfe-Shimmer equality method, the Ellman method, and the esterase assay, respectively. The results of the cytotoxic and anticancer activities of the compounds displayed that 6-bromotetrahydroquinoline (2), 6,8-dibromotetrahydroquinoline (3), 8-bromo-6-cyanoquinoline (10), 5-bromo-6,8-dimethoxyquinoline (12), the novel N-nitrated 6,8-dimethoxyquinoline (13), and 5,7-dibromo-8-hydroxyquinoline (17) showed a significant antiproliferative potency against the A549, HeLa, HT29, Hep3B, and MCF7 cancer cell lines (IC50 = 2-50 µg/ml) and low cytotoxicity (∼7-35%) as the controls, 5-fluorouracil and cisplatin. The compound-DNA linkages are hyperchromic or hypochromic, causing variations in their spectra. This situation shows that they can be bound to DNA with the groove-binding mode, with Kb value in the range of 2.0 × 103 -2.2 × 105 M-1 . Studies on human Gram(+) and Gram(-) pathogenic bacteria showed that the substituted quinolines exhibited selective antimicrobial activities with MIC values of 62.50-250 µg/ml. All tested quinoline derivatives were found to be effective inhibitors of acetylcholinesterase (AChE) and the human carbonic anhydrase I and II isoforms (hCA I and II), with Ki values of 46.04-956.82 nM for hCA I, 54.95-976.93 nM for hCA II, and 5.51-155.22 nM for AChE. As a result, the preliminary data showed that substituted quinolines displayed effective pharmacological features. Molecular docking studies were performed to investigate the binding modes and interaction energies for compounds 2-17 with AChE (PDB ID: 4EY6), hCA I (PDB ID: 1BMZ), and hCA II (PDB ID: 2ABE).

Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives.

Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT-DNA. Most of the enamine derivatives with IC50 values of 86-168 µM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5-fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (∼6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M-1 -2.3×104 M-1 . The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.

Antiproliferative Evaluation of Some 2-[2-(2-Phenylethenyl)-cyclopent-3-en-1-yl]-1,3-benzothiazoles: DFT and Molecular Docking Study.

The 2-[2-(2-phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were synthesized from the reactions of 7-benzylidenebicyclo[3.2.0]hept-2-en-6-ones with 2-aminobenzenethiol. The antiproliferative activities of 2-[2-(2-phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were determined against C6 (rat brain tumor) and HeLa (human cervical carcinoma cells) cell lines using BrdU cell proliferation ELISA assay. Cisplatin and 5-fluorouracil (5-FU) were used as standards. The most active compound was 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 cell lines with IC50 =5.89 µm value (cisplatin, IC50 =14.46 µm and 5-FU, IC50 =76.74 µm). Furthermore, the most active compound was 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa cell lines with IC50 =3.98 µm (cisplatin, IC50 =37.95 µm and 5-FU, IC50 =46.32 µm). Additionally, computational studies of related molecules were performed by using B3LYP/6-31G+(d,p) level in the gas phase. Experimental IR and NMR data were compared with the calculated results and were found to be compatible with each other. Molecular electrostatic potential (MEP) maps of the most active 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa and the most active 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 were investigated, aiming to determine the region that the molecule is biologically active. Biological activities of mentioned molecules were investigated with molecular docking analyses. The appropriate target protein (PDB codes: 1 M17 for the HeLa cells and 1JQH for the C6 cells) was used for 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole and 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole molecules exhibiting the highest biological activity against HeLa and C6 cells in the docking studies. As a result, it was determined that these molecules are the best candidates for the anticancer drug.

Structural, spectral characterization and molecular docking analyses of mer-ruthenium (II) complexes containing the bidentate chelating ligands.

In this study, we analyzed some monofunctional Ru (II) complexes containing chlorine, bromine and fluorine atoms around the central atom. The best calculation level among HF, B3LYP and M062X methods for [Ru (Cl-Ph-tpy)(NN)X]+ (X = F, Cl, Br) was determined in the light of Benchmark analysis and according to this analysis results, the best level is shown as B3LYP-LANL2DZ/6-31G(d). In addition to this, the spectroscopic data (IR, NMR and UV-Vis) were also obtained in agreement with experimental results. The tendency of anticancer activity and structural activity relationship (SAR) parameters are predicted with some quantum chemical methods. Surface and contour diagrams, as well as electron densities on mentioned complexes were interpreted through theoretically obtained results. Finally, the anticancer activity tendency of the relevant complexes on the human cervical carcinoma cell line (ID: 1 M17) is supported by molecular docking calculations.

Evaluation of carbonic anhydrase and paraoxonase inhibition activities and molecular docking studies of highly water-soluble sulfonated phthalocyanines.

The investigation of carbonic anhydrase and paraoxonase enzyme inhibition properties of water-soluble zinc and gallium phthalocyanine complexes ( 1 and 2 ) are reported for the first time. The binding of p-sulfonylphenoxy moieties to the phthalocyanine structure favors excellent solubilities in water, as well as providing an inhibition effect on carbonic anhydrase (CA) I and II isoenzymes and paraoxonase (PON1) enzyme. According to biological activity results, both complexes inhibited hCA I, hCA II, and PON1. Whereas 1 and 2 showed moderate hCA I and hCA II (off-target cytosolic isoforms) inhibitory activity (Ki values of 26.09 µM and 43.11 µM for hCA I and 30.95 µM and 33.19 µM for hCA II, respectively), they exhibited strong PON1 (associated with high-density lipoprotein [HDL]) inhibitory activity (Ki values of 0.37 µM and 0.27 µM, respectively). The inhibition kinetics were analyzed by Lineweaver-Burk double reciprocal plots. It revealed that 1 and 2 were noncompetitive inhibitors against PON1, hCA I, and hCA II. These complexes can be more advantageous than other synthetic CA and PON inhibitors due to their water solubility. Docking studies were carried out to examine the interactions between hCA I, hCA II, and PON1 inhibitors and metal complexes at a molecular level and to predict binding energies.