A mononuclear Cu(II) complex with 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine: Synthesis, crystal structure, DNA- and BSA-binding, molecular modeling, and anticancer activity against MCF-7, A-549, and HT-29 cell lines

Anjomshoa, Marzieh; Hadadzadeh, Hassan; Torkzadeh‐Mahani, Masoud; Fatemi, Seyed Jamilaldin; Adeli-Sardou, Mahboubeh; Rudbari, Hadi Amiri; Nardo, Viviana Mollica

doi:10.1016/j.ejmech.2015.04.020

Cited by 85 publications

(31 citation statements)

References 68 publications

(66 reference statements)

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“…These results show complexes 5 and 6 cannot compete for DNA-binding sites with GR and their interaction with DNA is external binding. Obtained results from competitive DNA-binding studies between metal complexes with EB [16,[20][21][22] are similar to obtained results with GR (Tables 1 and 2).…”

Section: Resultssupporting

confidence: 86%

“…Table 1 indicates obtained results from quenching of the emission band of the GR-DNA system at 592 nm with the addition of complexes. Table 2 shows obtained results from quenching of the emission band of the EB-DNA system at 592 nm with the addition of complexes in our previous reported [16,[20][21][22]. Furthermore, the quenching constants (K SV ) are calculated according to the Stern-Volmer equation (Eq.…”

Section: Resultsmentioning

confidence: 99%

“…The solution gave a ratio 1.89 at A 260 /A 280 , indicating that the DNA was sufficiently free from protein contamination [14]. (5) were prepared with using the procedure reported, respectively [15][16][17][18]. …”

Section: Experimental Materialsmentioning

confidence: 99%

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Competitive DNA-Binding Studies between Metal Complexes and GelRed as a New and Safe Fluorescent DNA Dye

Anjomshoa

Torkzadeh‐Mahani

2016

J Fluoresc

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The focus of this work is introduction of GelRed (GR) as a stable, sensitive and environmentally safe fluorescent DNA dye instead of the highly toxic ethidium bromide (EB). Competitive DNA-binding studies between metal complexes, [Cu(phen-dion)(phen)Cl]Cl (1), [Cu(phen-dione)(bpy)Cl]Cl (2), [Cu(dppt)2(H2O)]PF6 (3), [Ni(dppt)2Cl2] (4), [Zn(dppt)2Cl2] (5), and K3[Fe(CN)6] (6) (where phen-dione is 1,10-phenanthroline-5,6-dione, phen is 1,10- phenanthroline, bpy is 2,2'-bipyridine, and dppt is 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine), and GelRed have been investigated under physiological conditions by fluorescence spectroscopy. This simple method can reveal the binding affinity and mode of metal complexes with DNA. The method is based on the decrease of fluorescence derived from the displacement of GelRed from DNA by metal complexes. The % fluorescence decrease is directly related to the extent of DNA binding. Results indicate the DNA binding affinities of complexes follow the order 3 > 4 > 1 > 2 > 5 > 6. The significant quenching of the emission band of the GR-DNA with the addition of complexes 1, 3, and 4 suggests that complexes compete for DNA-binding sites with GR and displace GR from the GR-DNA, which is usually characteristic of the intercalative interaction of compounds with DNA. A small quenching of the emission band of the GR-DNA with the addition of the complex 2 was observed that show the complex weaker competes for DNA-binding sites with GR than complexes 1, 3, and 4. Results show complexes 5 and 6 cannot compete for DNA-binding sites with GR and their interaction with DNA is external binding (groove or electrostatic bindig).

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Section: Resultssupporting

confidence: 86%

Section: Resultsmentioning

confidence: 99%

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Competitive DNA-Binding Studies between Metal Complexes and GelRed as a New and Safe Fluorescent DNA Dye

Anjomshoa

Torkzadeh‐Mahani

2016

J Fluoresc

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“…These results reveal that the IC 50 value for complex (1) against HT-29 is very smaller than reported IC 50 value for the cisplatin drug and, consequently, the HT-29 cell line is more sensitive to this complex than cisplatin [54]. The IC 50 values obtained for these complexes are larger than other Cu(II) complex (except IC 50 value for complex (1) against HT-29) [55]. Fig.…”

Section: In Vitro Cytotoxicity Studiesmentioning

confidence: 63%

In vitro DNA and BSA-binding, cell imaging and anticancer activity against human carcinoma cell lines of mixed ligand copper(II) complexes

Anjomshoa

Torkzadeh‐Mahani

2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…[1] Apart from their use as intermediates in the construction of various heterocyclic systems via hetero-DielsÀAlder cycloadditions, [2] 1,2,4-triazine derivatives are also used as key metal coordinating ligands and fluorescent sensor. [1] Apart from their use as intermediates in the construction of various heterocyclic systems via hetero-DielsÀAlder cycloadditions, [2] 1,2,4-triazine derivatives are also used as key metal coordinating ligands and fluorescent sensor.…”

Section: Introductionmentioning

confidence: 99%

DBU‐Catalyzed [3+3] and [3+2] Annulation Reactions of Azomethine Ylides with α‐Diazocarbonyls as N‐Terminal Electrophiles: Modular, Atom‐Economical Access to 1,2,4‐Triazine and 1,2,4‐Triazole Derivatives

et al. 2018

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The DBU-catalyzed [3 + 3] and [3 + 2] cyclization reactions of azomethine ylides with adiazocarbonyls as N-terminal electrophiles have been developed. These reactions involve a sequential intermolecular nucleophilic addition/intramolecular cyclization/oxidation procedure. By the assembly of readily available starting materials, these transformations offer novel, highly efficient one-pot syntheses of various functionalized 1,2,4-triazine and 1,2,4-triazole derivatives in an atom-economical manner under ambient and metal-free conditions in a high regio-and diastereoselective manner.

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A mononuclear Cu(II) complex with 5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine: Synthesis, crystal structure, DNA- and BSA-binding, molecular modeling, and anticancer activity against MCF-7, A-549, and HT-29 cell lines

Cited by 85 publications

References 68 publications

Competitive DNA-Binding Studies between Metal Complexes and GelRed as a New and Safe Fluorescent DNA Dye

Competitive DNA-Binding Studies between Metal Complexes and GelRed as a New and Safe Fluorescent DNA Dye

In vitro DNA and BSA-binding, cell imaging and anticancer activity against human carcinoma cell lines of mixed ligand copper(II) complexes

DBU‐Catalyzed [3+3] and [3+2] Annulation Reactions of Azomethine Ylides with α‐Diazocarbonyls as N‐Terminal Electrophiles: Modular, Atom‐Economical Access to 1,2,4‐Triazine and 1,2,4‐Triazole Derivatives

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