Gold(III) complex from pyrimidine and morpholine analogue Schiff base ligand: Synthesis, characterization, DFT, TDDFT, catalytic, anticancer, molecular modeling with DNA and BSA and DNA binding studies

Sankarganesh, Murugesan; Raja, Jeyaraj Dhaveethu; Revathi, Nagaraj; Solomon, Rajadurai Vijay; Raju, Senthil Kumar

doi:10.1016/j.molliq.2019.111655

Cited by 63 publications

(23 citation statements)

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“…The most common anticancer strategy is promoting a higher oxidative damage in biomolecules to trigger the apoptosis process [ 78 ]. However, there are some examples where a relationship between antioxidant and antitumor behavior has been demonstrated [ 79 , 80 ], even with gold(III) complexes [ 54 , 81 , 82 ]. In this study, we evaluated the oxidation levels of the carbonyl groups present in proteins by the established method of 2,4-dinitrophenylhydrazine (DNPH) [ 83 ].…”

Section: Resultsmentioning

confidence: 99%

Selective Anticancer and Antimicrobial Metallodrugs Based on Gold(III) Dithiocarbamate Complexes

et al. 2021

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New dithiocarbamate cycloaurated complexes have been synthesized and their physicochemical and in vitro antitumor properties have been evaluated. All the performed studies highlighted good transport through the blood and biodistribution, according to the balance between the properties of hydrophilicity/lipophilicity and the binding of moderate strength to the BSA protein. Furthermore, none of the complexes exhibited reduction or decomposition reactions, presenting excellent physiological stability. The in vitro cytotoxic effect was evaluated on human colon cancer cell line Caco-2/TC7, and the complexes showed great antiproliferative activity and excellent selectivity, as much less effect was detected on normal Caco-2/TC7 cells. Most of the complexes exhibit antiproliferative activity that was better than or similar to auranofin, and at least nine times better than that of cisplatin. Its action mechanism is still under discussion since no evidence of cell cycle arrest was found, but an antioxidant role was shown for some of the selective complexes. All complexes were also tested as antimicrobial drugs, exhibiting good activity towards S. aureus and E. coli. bacteria and C. albicans and C. neoformans fungi.

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Section: Resultsmentioning

confidence: 99%

Selective Anticancer and Antimicrobial Metallodrugs Based on Gold(III) Dithiocarbamate Complexes

et al. 2021

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“…Also, docking results indicated that complexes 4-9 can be bound to BSA to subdomain IIA (site I) forming hydrogen bonds, while electrostatic and hydrophobic interactions had the major impact on binding (Radisavljević et al, 2019). For complex 11 was proved the presence of hydrogen bonds with Arg185, Leu189, Thr190, Ser192, Pro240, Glu424, Ser428, Ile552, and Arg458 on the active site of BSA (Sankarganesh et al, 2019).…”

Section: Computational Calculationsmentioning

confidence: 95%

“…The interactions between newly synthesized gold(III) complexes that contain structurally distinct nitrogen-donor ligands (Figure 1), such as 2,6-bis(5-tert-butyl-1H-pyrazol-3-yl)pyridine (complex 1), 2,6-bis(5-tert-butyl-1-methyl-1H-pyrazol-3yl)pyridine (complex 2), 2,6-bis((4S, 7R)−1,7,8,8-tetramethyl-4,5,6,7-tetrahydro-1H-4,7-methanoindazol-3-yl)pyridine (complex 3), 1,4-diaminobutane (complexes 4 and 7), 1,6diaminohexane (complexes 5 and 8), 1,8-diaminooctane (complexes 6 and 9), combination of 2,2 ′ -bipyridine and N-(3-((4-nitrophenyl) thio)phenyl)methanediimine (complex 10), and (Z)-1-(4-morpholinophenyl)-N-((4-(trifluoromethyl) pyrimidin-2-yl)methyl)methanimine (complex 11) (Radisavljević et al, 2018(Radisavljević et al, , 2019Sankarganesh et al, 2019;Tabrizi et al, 2020), and primary biomolecules were examined by different experimental methods. These complexes were selected having in mind that the presence of different nitrogen-donor inert ligands in the structure of some gold(III) complexes have great potential to stabilize metal ion and improve its binding affinity toward biomolecules under physiological conditions (Radisavljević et al, 2019).…”

Section: Biological Targets For Gold(iii) Complexesmentioning

confidence: 99%

“…The first metal-based anticancer agent was cisplatin, discovered in 1969 (Rosenberg et al, 1969). After application of cisplatin, other platinum(II) complexes (carboplatin, oxaliplatin) were employed with the same aim (Sankarganesh et al, 2019). The promising results of usage of platinum complexes in medicinal purpose have led to the synthesis of different transition metal ion compounds and study of their potential antitumor activity (Jung and Lippard, 2007;Kim et al, 2008;Garcia et al, 2009;Wu et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

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Gold(III) Complexes: An Overview on Their Kinetics, Interactions With DNA/BSA, Cytotoxic Activity, and Computational Calculations

Radisavljević

Petrović

2020

Front. Chem.

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In the last few years, metallodrugs play a key role in the development of medicinal chemistry. The choice of metal ion, its oxidation state and stability, and the choice of inert and labile ligands are just some of the very important facts which must be considered before starting the synthesis of complexes with utilization in medicinal purpose. As a result, a lot of compounds of different transition metal ions found application for diagnostic and therapeutic purpose. Beside all, gold compounds have attracted particular attention. It is well-known that gold compounds could be used for the treatment of cancer, HIV, rheumatoid arthritis (chrysotherapy), and other diseases. This metal ion has unoccupied d-sublevels and possibility to form compounds with different oxidation states, from −1 to +5. However, gold(I) and gold(III) complexes are dominant in chemistry and medicine. Especially, gold(III) complexes are of great interest due to their structural similarity with cisplatin. Accordingly, this review summarizes the chemistry of some mononuclear and polynuclear gold(III) complexes. Special attention is given to gold(III) complexes with nitrogen-donor inert ligands (aliphatic or aromatic that have a possibility to stabilize complex) and their kinetic behavior toward different biologically relevant nucleophiles, mechanism of interaction with DNA/bovine serum albumin (BSA), cytotoxic activity, as well as computational calculations.

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“…[1][2][3][4][5][6][7][8][9][10]. Morpholine and its phenyl substituted derivatives have been extensively utilized as antimalarial, antioxidant, antimicrobial, anti-inflammatory and analgesic properties [11][12][13][14][15][16][17][18][19]. The Schiff base complexes have been used in catalytic reactions [20,21] and as models for biological system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectral studies, molecular structure determination by single crystal X-ray diffraction of (E)-1-(((3-fluoro-4-morpholinophenyl)imino)methyl)napthalen-2-ol and computational studies by Austin model-1(AM1), MM2 and DFT/B3LYP

Thandra

Bojja²,

Ramachandraiah

2020

SN Appl. Sci.

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E)-1-(((3-fluoro-4-morpholinophenyl)imino)methyl)napthalen-2-ol (1) has been synthesized and its computational investigations have been carried out through semi-empirical Austin Model-1 (AM1), SCF-MM2 and DFT/B3LYP methods in relation to its solid state molecular structure determined by single-crystal X-ray diffraction to correlate structural parameters in the gaseous state under vacuum to empirical those of the molecule in its crystalline solid state. The compound is reported to crystallize in monoclinic system in space group P21/n with crystal data as a = 15.1589(12) Å, b = 7.4349(5) Å, c = 15.4287(13) Å, β = 98.340(4), V = 1720.5(2) Å 3 , Z = 4, density = 1.353 Mg/m 3 , F (000) = 736, T = 296(2) K, obtained through reflections collected/unique = 13,631/4112. The shifts in various relevant bond lengths, bond angles, dihedral angles, etc. under AM1, B3LYP and MM2 treatments are discussed.Graphic abstract (E)-1-(((3-fluoro-4-morpholinophenyl)imino)methyl)napthalen-2-ol has been synthesized and its structural aspects in its solid state obtained by single crystal XRD have been compared with those in its gas phase evaluated by Austin Model-1 under AM1, DFT/B3LYP and ChemSoft's ChemDraw Pro under MM2 Calculations.

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Gold(III) complex from pyrimidine and morpholine analogue Schiff base ligand: Synthesis, characterization, DFT, TDDFT, catalytic, anticancer, molecular modeling with DNA and BSA and DNA binding studies

Cited by 63 publications

References 30 publications

Selective Anticancer and Antimicrobial Metallodrugs Based on Gold(III) Dithiocarbamate Complexes

Selective Anticancer and Antimicrobial Metallodrugs Based on Gold(III) Dithiocarbamate Complexes

Gold(III) Complexes: An Overview on Their Kinetics, Interactions With DNA/BSA, Cytotoxic Activity, and Computational Calculations

Synthesis, spectral studies, molecular structure determination by single crystal X-ray diffraction of (E)-1-(((3-fluoro-4-morpholinophenyl)imino)methyl)napthalen-2-ol and computational studies by Austin model-1(AM1), MM2 and DFT/B3LYP

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