Synthesis, characterization, DNA interaction, and antitumor activities of mixed-ligand metal complexes of kaempferol and 1,10-phenanthroline/2,2′-bipyridine

Wang, Qin; Huang, Min; Huang, Yu; Zhang, Jinsheng; Zhou, Gui-Feng; Zeng, Ren-Quan; Xia, Yang

doi:10.1007/s00044-013-0863-2

Cited by 26 publications

(11 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cisplatin, besides being one of the oldest antitumor drugs, is also one of the most studied . However, compounds derived from natural flavonoids widely known for their antibacterial, antiviral, antioxidant, and anti‐inflammatory biological activities have been shown to be promising anticancer agents, mainly the kaempferol‐type polyphenol molecule …”

Section: Introductionmentioning

confidence: 99%

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

Souza

Soeiro

2018

Int J of Quantum Chemistry

View full text Add to dashboard Cite

The polyphenol compound Kaempferol, a relevant member of the class of flavonoids, is a good example where coordination to Zn(II) ion was found to improve the anticancer effects compared to the free ligand. Determination of the metal‐complex molecular structure (and binding sites on Kaempferol) in the liquid phase is fundamental for an understanding of biological activities. Experimental UV‐Vis and EPR data only provide indirect evidence or limited structural information. Therefore, theoretical study of structural and spectroscopic properties of the metal‐polyphenol complex, using computational quantum chemistry methods, is certainly relevant as starting point for the investigation of mechanism of action at a molecular level. In this article, we used the density functional theory (DFT) methodology to predict the molecular structure of [Zn(Kaempferol)(H2O)n]+ and [Zn(Kaempferol)2(H2O)n] complexes (n = 0, 2, or 4) and B‐ring nonplanar conformation of flavonoid using as strategy the best match between theoretical and experimental 1H NMR, IR, and UV‐Vis spectroscopic data in solution. These are valuable information for further studies involving structure‐activity relationship.

show abstract

Section: Introductionmentioning

confidence: 99%

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

Souza

Soeiro

2018

Int J of Quantum Chemistry

View full text Add to dashboard Cite

show abstract

“…Kinetic studies have been previously carried out on several chemical and biological compounds but there has been growing interest towards transition metal complexes, this is because of the wide range of applications of metal complexes resulting from the peculiarity in the physical and chemical properties of transition metals that form such complexes. The metal complexes of diimine ligands such as 1,10-phenanthroline and 2,2'-bipyridine have received much research interest because of their versatile roles as building blocks in synthesis as well as their bioinorganic and biomedicinal applications (Wang et al 2014, Ahmed & Khaled 2015, Gopinathan & Arumugham 2015, Molphy et al 2015. Based still on the peculiarity of transition metal properties, metal complexes can either function as a reductant or an oxidant in an electron transfer reaction with other metal complexes or with other compounds, thus have attracted a lot of kinetic studies on them.…”

Section: Introductionmentioning

confidence: 99%

Electron transfer reaction of Tris(1,10-phenanthroline) cobalt(III) complex [Co(phen)3]3+ and thiosulphate ion (S2O32âˆ’) in an aqueous acidic medium

Osunkwo

Nkole

Onu

et al. 2018

IJAC

View full text Add to dashboard Cite

The electron transfer reaction of Tris (1,10-phenanthroline)cobalt(III) complex by thiosulphate ion has been studied in an aqueous acidic medium. Stoichiometric determination shows that for one mole of the oxidant that was reduced, one mole of the reductant was consumed; the reaction conforms to an overall equation: 2[Co(phen)3]3+ + 2S2O32− → 2[Co(phen)3]2+ + S4O62− Kinetics study carried out under pseudo-first order condition shows that the reaction proceeded via a one-way acid-dependent pathway and was third order overall; zero order with respect to the oxidant concentration, second order with respect to the reductant concentration and first order with respect to the hydrogen ion concentration. The empirical rate law conforms to the equation: − {Co(phen)3}3+] = a [H+] [S2O32−]2 ‘a’ = 128.26 dm6 mol−2 s−1: at [H+] = 2.0 × 10−2 mol dm−3, µ = 0.4 mol dm−3 (NaCl), T = 28 ± 1˚C and λmax = 495 nm.The rate of reaction increased at the increase in ionic strength and at the decrease in medium dielectric constant. Added cations and anions catalyzed and inhibited the reaction rates respectively. The Michaelis-Menten plot of 1/k1 versus 1/[S2O32−]2 started from the origin. Hence based on spectroscopic investigation, thermodynamic information from temperature dependence studies and kinetic evidence from Michaelis–Menten plots and the interactions with added ions, an outer-sphere mechanism has been rationalized for this reaction. The mechanistic scheme of the reaction was proposed via the stated mechanistic route.

show abstract

“…Therefore, their affinities toward ‘‘hard’’ ligands with oxygen donor atoms, such as flavonoid derivatives, will be very strong [3]. The design of Ln complexes is focused on potential application in areas such as extraction and separation, catalysis, nonlinear optics (NLO), luminescent probes, magnetism, or is pointing towards therapeutic potential as antioxidant, anticancer [4,5,6], or antimicrobial agents [7]. Because of their long wavelength emission and lifetimes, Ln complexes have the potential for application as sensors and probes in biological and biomedical research [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Investigation of New Bio-Relevant Complexes of Lanthanides with 5-Hydroxyflavone: DNA Binding and Protein Interaction Studies

et al. 2016

View full text Add to dashboard Cite

Abstract:In the present work, we attempted to develop new metal coordination complexes of the natural flavonoid 5-hydroxyflavone with Sm(III), Eu(III), Gd(III), Tb(III). The resultant hydroxo complexes have been characterized by a variety of spectroscopic techniques, including fluorescence, FT-IR, UV-Vis, EPR and mass spectral studies. The general chemical formula of the complexes is [Ln(C 15 H 9 O 3 ) 3 (OH) 2 (H 2 O) x ]·nH 2 O, where Ln is the lanthanide cation and x = 0 for Sm(III), x = 1 for Eu(III), Gd(III), Tb(III) and n = 0 for Sm(III), Gd(III), Tb(III), n = 1 for Eu(III), respectively. The proposed structures of the complexes were optimized by DFT calculations. Theoretical calculations and experimental determinations sustain the proposed structures of the hydroxo complexes, with two molecules of 5-hydroxyflavone acting as monoanionic bidentate chelate ligands. The interaction of the complexes with calf thymus DNA has been explored by fluorescence titration and UV-Vis absorption binding studies, and revealed that the synthesized complexes interact with DNA with binding constants (K b )~10 4 . Human serum albumin (HSA) and transferrin (Tf) binding studies have also been performed by fluorescence titration techniques (fluorescence quenching studies, synchronous fluorescence spectra). The apparent association constants (K a ) and thermodynamic parameters have been calculated from the fluorescence quenching experiment at 299 K, 308 K, and 318 K. The quenching curves indicate that the complexes bind to HSA with smaller affinity than the ligand, but to Tf with higher binding affinities than the ligand.

show abstract

Synthesis, characterization, DNA interaction, and antitumor activities of mixed-ligand metal complexes of kaempferol and 1,10-phenanthroline/2,2′-bipyridine

Cited by 26 publications

References 34 publications

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

Electron transfer reaction of Tris(1,10-phenanthroline) cobalt(III) complex [Co(phen)3]3+ and thiosulphate ion (S2O32âˆ’) in an aqueous acidic medium

Synthesis and Structural Investigation of New Bio-Relevant Complexes of Lanthanides with 5-Hydroxyflavone: DNA Binding and Protein Interaction Studies

Contact Info

Product

Resources

About

Synthesis, characterization, DNA interaction, and antitumor activities of mixed-ligand metal complexes of kaempferol and 1,10-phenanthroline/2,2′-bipyridine

Cited by 26 publications

References 34 publications

A DFT study of molecular structure and 1H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

A DFT study of molecular structure and 1H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

Electron transfer reaction of Tris(1,10-phenanthroline) cobalt(III) complex [Co(phen)3]3+ and thiosulphate ion (S2O32âˆ’) in an aqueous acidic medium

Synthesis and Structural Investigation of New Bio-Relevant Complexes of Lanthanides with 5-Hydroxyflavone: DNA Binding and Protein Interaction Studies

Contact Info

Product

Resources

About

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity

A DFT study of molecular structure and ¹H NMR, IR, and UV‐Vis spectrum of Zn(II)‐kaempferol complexes: A metal‐flavonoid complex showing enhanced anticancer activity