Copper(II) and platinum(II) compounds with pyrene-appended dipicolylamine ligand: syntheses, crystal structures and biological evaluation

Yuan, Zeli; Wang, Lei; Shen, Xiao-Min; Yang, Xiaoqing; Huang, Jian‐Dong; Wei, Gang

doi:10.1007/s10847-015-0473-3

Cited by 8 publications

(5 citation statements)

References 29 publications

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“…The delicate structural adjustment of IMs toxicity to obtain anticancer activities has led to numerous recent developments, including the conception of N‐ heterocyclic carbenes (NHC), [53–55] whose σ‐donor character highly stabilizes them when complexing transition metals, with no risk of degradation in physiological media. The inclusion of polyaromatic ligands in complexes to obtain biological properties only led to a few studies, [56,57] and the use of these compounds fluorescence to study their interaction with DNA has barely been reported [58,59] …”

Section: Theranosticsmentioning

confidence: 99%

“…IM showing anticancer properties (molecule shown before radioiodination). [49] studies, [56,57] and the use of these compounds fluorescence to study their interaction with DNA has barely been reported. [58,59] Kazeminasab et al [59] recently produced a rather complete study about a new luminescent NHC ligand (4) bearing a pyrene fragment, and two complexes ( 5) and ( 6) based on palladium, binding 4 (Figure 11).…”

Section: Figurementioning

confidence: 99%

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Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

2021

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Light and cognate phenomena, e. g., luminescence are powerful tools endowed with great sensitivity to explore the infinitely small. Molecular salts, especially those based on imidazolium units, are granted with original properties and structural versatility. Associated with fluorophores, they constitute highly bioavailable platforms. Their interactions with negatively charged species and biological membranes as well as their controllable cytotoxicity imparted their applications as anion receptors, but also a promising potential as antibacterial and anticancer agents whose mechanism of action can be observed using luminescence, opening the possibility of theranostics (therapy and diagnosis). One of the other assets of imidazolium salts is their flexible amphipathic character which promotes their self‐organizations into liquid‐crystal mesophases and their ability to mimic lipids. Combining luminescence to these amphipathic properties opens new prospects, e. g., following gene or drug delivery inside cells. These salts, all‐in‐one, should lead to new tools for biologists, as well as active theranostic molecules.

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Section: Theranosticsmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

2021

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“…Various applications have been reported for pyrene‐imidazolium derivatives such as fluorescent sensors for ATP, G‐quadruplex and lanthanide ions in aqueous solutions . So far there have been only a few studies on the biological properties of complexes containing polyaromatic hydrocarbons in their ligand scaffold …”

Section: Introductionmentioning

confidence: 99%

Luminescent Palladacycles Containing a Pyrene Chromophor; Synthesis, Biological and Computational Studies of the Interaction with DNA and BSA

et al. 2019

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One of the most active areas within the field of bioorganometallic chemistry, complexes of N-heterocyclic carbenes (NHCs), have recently gained interest. Herein, we report two luminescent palladium N-heterocyclic carbene complexes; namely [Pd {(C,N)-C 6 H 4 CH 2 NH(CH 2 CH 3 )}(1)] (2) and [Pd{(C,N)-C 6 H 4 CH 2 NH 2 }(1)] (3) (1 = 1-methyl-3-(2-oxo-2-(pyren-1-yl)ethyl)-2,3-dihydroimidazol-2-ylidene) which were synthesized from the reaction of luminescent imidazolium salt (1(H)Br) and binuclear Palladacycles. The interactions of them with CT-DNA evaluated via absorption, emission and CD spectral techniques as well as measurements of viscosity and thermal denaturation and the results have been shown that they bounded to CT-DNA by intercalation and groove binding modes. The in vitro cytotox-icity of compounds 2-3 and 1(H)Br on human breast (MCF-7) and cervical epithelial carcinoma (HeLa) cancer cells lines, indicated the wide range of anticancer activities of them with low IC 50 values. Moreover, based on the protein binding ability studies, the intrinsic fluorescence of BSA could be strongly quenched by compounds via a static quenching mechanism. Competitive binding study using Eosin, Digoxin and Ibuprofen as site markers, indicated that the compounds could bind to sites I and II on BSA structure. Finally, all data obtained from biophysical studies were validated by molecular modeling study. Computational results showed that palladium complexes have the potential for detection of mismatch DNA.

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“…In particular, oxovanadium salts are less expensive than K 2 PtCl 4 , RuCl 3 or VCl 3 and are therefore attractive for vanadium-based research and development of inexpensive drugs. Current research suggests that transformed cells maintain an abnormal redox homeostasis that helps them to obtain a high level of genetic instability, which is conducive to cancer progression [10][11][12]. Vanadium's intrinsic redox activity can generate reactive oxygen species (ROS).…”

Section: Introductionmentioning

confidence: 99%

Syntheses, crystal structures and in vitro anticancer activities of oxovanadium(IV) complexes of amino acid Schiff base and 1,10-phenanthroline ligands

Cao

et al. 2016

Transit Met Chem

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Four oxovanadium(IV) complexes, namely [VO(desa-met)(phen)]ÁMeOHÁ2H 2 O (1) (desa-met = Schiff base derived from 4-(diethylamino)salicylaldehyde and DLmethionine, phen = 1,10-phenanthroline), [VO(o-van-met)-(phen)]ÁMeOHÁCH 2 Cl 2 Á3H 2 O (2) (o-van-met = Schiff base derived from o-vanillin and DL-methionine), [VO(dtbsnapa)(phen)]Á2H 2 O (3) (dtbs-napa = Schiff base derived from 3,5-di-tert-butyl salicylaldehyde and 3-(1-naphthyl)-Lalanine) and [VO(hyna-napa)(phen)]Á1.5H 2 O (4) (hynanapa = Schiff base derived from 2-hydroxy-1-naphthaldehyde and 3-(1-naphthyl)-L-alanine), were synthesized and characterized by IR, HRMS, UV-vis spectra, molar conductance and single-crystal X-ray diffraction (XRD). X-ray structural analysis showed that the V(IV) atoms in all four complexes are six-coordinated in a distorted octahedral environment. In the crystals of complexes 1 and 2, p-p stacking interactions together with hydrogen bonds connect the molecular units into 2D networks. Meanwhile, CH-p stacking interactions are observed between the aromatic rings in the crystals of 1 and 4, while the p-p stacking interactions between aromatic rings in the crystals of 2 and 3 are arranged with a face-to-face mode. The in vitro anticancer activities of these complexes against A-549 and HeGp2 cells were tested by MTT assay.

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Copper(II) and platinum(II) compounds with pyrene-appended dipicolylamine ligand: syntheses, crystal structures and biological evaluation

Cited by 8 publications

References 29 publications

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

Luminescent Imidazolium Salts as Bright Multi‐Faceted Tools for Biology

Luminescent Palladacycles Containing a Pyrene Chromophor; Synthesis, Biological and Computational Studies of the Interaction with DNA and BSA

Syntheses, crystal structures and in vitro anticancer activities of oxovanadium(IV) complexes of amino acid Schiff base and 1,10-phenanthroline ligands

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