Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes

Radisavljević, Snežana; Ćoćić, Dušan; Jovanović, Snežana; Šmit, Biljana; Petković, Marijana; Milivojević, Nevena; Planojević, Nevena; Marković, Snežana D.; Petrović, Biljana

doi:10.1007/s00775-019-01716-8

Cited by 20 publications

(11 citation statements)

References 63 publications

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“…The same conclusion was derived for structurally similar complexes with terpyridine ligands (Liu et al, 1995;Messori et al, 2005;Shi et al, 2006). The other method, fluorescence spectroscopy, was employed in the aim to clarify the mode 1 | The DNA-binding constants (K b ) and Stern-Volmer constants (K sv ) from EB-DNA fluorescence for complexes 1-9 and bovine serum albumin (BSA) constants and parameters (K sv , k q , K, and n) derived for complexes 4-9 (Radisavljević et al, 2018(Radisavljević et al, , 2019.…”

Section: Biological Targets For Gold(iii) Complexesmentioning

confidence: 87%

“…In the case of complexes 4-9, the presence of diamine length allowed better interaction with DNA. 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%

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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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Section: Biological Targets For Gold(iii) Complexesmentioning

confidence: 87%

Section: Computational Calculationsmentioning

confidence: 95%

Section: Biological Targets For Gold(iii) Complexesmentioning

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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“…The study of the interaction of gold-drugs with BSA affords information on the distribution, on the free concentration, on the metabolism and on the efficacy of the gold compound (Radisavljević et al, 2019). The BSA protein has large homology with Human Serum Albumin (HSA) and the quenching of the intrinsic tryptophan fluorescence represents a good tool to deeply investigate the possible interaction of our metallodrugs with BSA in an attempt to characterize the fate of the gold compounds once they are in physiological environments.…”

Section: Protein Binding Studiesmentioning

confidence: 99%

Multi-Targeted Anticancer Activity of Imidazolate Phosphane Gold(I) Compounds by Inhibition of DHFR and TrxR in Breast Cancer Cells

et al. 2021

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A class of phosphane gold(I) compounds, made of azoles and phosphane ligands, was evaluated for a screening on the regards of Breast Cancer cell panels (BC). The compounds possess N-Au-P or Cl-Au-P bonds around the central metal, and they differ for the presence of aprotic or protic polar groups in the azoles and/or the phosphane moieties to tune their hydrophilicity. Among the six candidates, only the compounds having the P-Au-N environment and not displaying neither the hydroxyl nor carboxyl groups in the ligands were found active. The compounds were screened by MTT tests in SKBR3, A17, and MDA-MB231 cancer cells, and two compounds (namely the 4,5-dicyano-imidazolate-1yl-gold(I)-(triphenylphosphane, 5, and 4,5-dichloro-imidazolate-1yl-gold(I)-triphenylphosphane, 6) were found very cytotoxic, with the most active with an IC50 value of 3.46 μM in MDA-MB231 cells. By performing enzymatic assays in the treated cells lysates, the residual enzymatic activity of dihydrofolate reductase (DHFR) has been measured after cell treatment for 4 or 12 h in comparison with control cells. Upon 12 h of treatment, the activity of DHFR was significantly reduced in both SKBR3 and A17 cells by compounds 5 and 6, but not in human MDA-MB231 cells; interestingly, it was found remarkably high after 4 h of treatment, revealing a time dependence for the DHFR enzymatic assays. The DHFR inhibition data have been compared to those for the thioredoxin reductase (TrxR), the most recognized molecular target for gold compounds. For this latter, similar residual activities (i.e., 37 and 49% for the match of SKBR3 cells and compound 5 or 6, respectively) were found. Binding studies on the regards of ct-DNA (calf-thymus-DNA) and of plasma transporters proteins, such as BSA (bovine serum albumin) and ATF (apo transferrin), were performed. As expected for gold compounds, the data support strong binding to proteins (Ksv values range: 1.51 ÷ 2.46 × 104 M−1) and a weaker interaction with ct-DNA's minor groove (Ksv values range: 1.55 ÷ 6.12 × 103 M−1).

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“…[49] However, BSA is the most studied conjugate protein due to the homology of structure with HSA, therefore, mimics in reactivity to study various metal-based complexes. [50,51] A huge number of metal complexes including mononuclear and poly-nuclear metals like Pt 2 + , Cu 2 + , Zn 2 + , Ni 2 + , and Co 2 + , complexes with various ligands have been investigated for their interaction studied with BSA for their binding ability. [52][53][54] Usually binding of the drug to protein molecules changed microenvironment around aromatic amino acid residue.…”

Section: Antioxidant Potentialmentioning

confidence: 99%

Bioactivity and DNA/BSA Interactions of Selenium N‐Heterocyclic Carbene Adducts

et al. 2020

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In wake of promising biomedical applications of organo‐selenium compounds, the present work was planned to synthesize selenium adducts (1 s‐‐4 s) and their respective azolium ligands (1 a–4 a), which were subsequently authenticated by various analytical and spectroscopic techniques like microanalysis, UV‐Visible, FT‐IR, 1H & 13C NMR and Electrospray Ionisation‐Mass Spectrometry (ESI‐MS). Moreover, the synthesized compounds were tested for their biological potential like antioxidant, antimicrobial, hemolytic, DNA and Bovin Serum Albumin (BSA) interactions, stability and lipophilicity using in‐vitro models. All the compounds were found stable in solution form for studied period 12–68 hours and showed good lipophilic values in the range of logP 0.66–0.85. In context to biological activities, selenium compounds showed better antimicrobial (ranging 17.4±0.5–25.3±0.8 mm against S. aureus and 18.6±0.7–24.1±0.9 against E.coli at concentration of 0.3 mg/mL for both strains) and antioxidant potential (IC50 ranging 40.0–62.0 μg/mL for DPPH solutions) compared to respective ligands. The interaction study of compounds (1 s–4 s) to DNA and BSA showed prominent binding affinity.

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Synthesis, characterization, DFT study, DNA/BSA-binding affinity, and cytotoxicity of some dinuclear and trinuclear gold(III) complexes

Cited by 20 publications

References 63 publications

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

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

Multi-Targeted Anticancer Activity of Imidazolate Phosphane Gold(I) Compounds by Inhibition of DHFR and TrxR in Breast Cancer Cells

Bioactivity and DNA/BSA Interactions of Selenium N‐Heterocyclic Carbene Adducts

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