Rhenium(II) nitrosyl complexes: synthesis, characterization, DFT calculations and DNA nuclease activity

Ghosh, Shouvik; Paul, Shiv Shankar; Mitra, Joyee; Mukherjea, Kalyan K.

doi:10.1080/00958972.2014.924622

Cited by 13 publications

(7 citation statements)

References 65 publications

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“…The absorbance of complex was found to be decreased with increasing amount of CT‐DNA without any visible shift of wavelength (Figure ). The observed hypochromicity suggests that the complex might bind to the minor groove of DNA by partial intercalation . The binding constant of the DNA‐complex species was calculated to be (8.14 ± 0.03) x10 3 M −1 which suggests that the complex binds to DNA with an affinity much less than that of classical intercalators …”

Section: Resultsmentioning

confidence: 99%

Biomimicking Oxidative Bromination and DNA Nuclease Activities of a New Structurally Characterised Oxido-Diperoxidomolybdenum(VI) Complex

et al. 2017

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A new oxido‐diperoxido molybdenum complex, [MoO(O2)2(AA)]PPh4 (AA=anthranilic acid) has been designed and synthesized. The Structural characterisation suggests that the molybdenum centre is heptacoordinated with a slight distorted pentagonal bipyramidal geometry. The pentagonal plane is completed with four oxygen atoms from two peroxido moiety and one oxygen atom from the ligand carboxylate group. Among the two axial positions one is occupied by an oxygen atom of the oxido group and the other is occupied by an oxygen atom from the ligand carboxylate moiety. The biomimicking multifunctionality of this molybdenum(VI) complex has been exhibited by the application of it as a catalyst in peroxidative bromination, whereas the nuclease activity has been established by DNA cleavage. The catalytic studies suggest that the present compound is a good biological peroxidase mimic. The DNA binding of the molybdenum complex has been studied by various physicochemical tools like UV–vis, fluorescence, viscosity. The intrinsic binding constant of the complex with DNA is calculated to be (8.14 ± 0.03) x103 M−1. All the physicochemical studies and the viscosity measurements reveal that the complex is a groove binder to CT‐DNA. The extent of ability of the complex to induce DNA cleavage was studied by gel electrophoresis techniques. The complex has been found to exhibit cleavage of pUC19 plasmid DNA with good efficiency.

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Section: Resultsmentioning

confidence: 99%

Biomimicking Oxidative Bromination and DNA Nuclease Activities of a New Structurally Characterised Oxido-Diperoxidomolybdenum(VI) Complex

et al. 2017

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“…[Re(NO)(CN) 4 (H 2 O)] -PhenH + . (3H 2 O)(Phen) was reported to interact with calf thymus DNA through partial intercalation into DNA bases but its cytotoxicity was not reported [25]. Re III complexes (d 4 ) are anticipated to be more inert to ligand exchange than d 2 Re V complexes [26].…”

Section: Chemical Structuresmentioning

confidence: 99%

“…Likewise, the structure-activity relationships of (diimines)Re(CO) 3 complexes with different sulfonato and carboxylato group as axial ancillary ligand in hormone-dependent MCF-7 and hormone-independent triple negative MDA-MB231 breast cancer cells suggested that the cytotoxic effects increased with their lipoliphilicy and that could be related with their DNA-binding ability [80]. [25]. Re(III) complexes, as tetrapropionato-diRe (III) [82], or cis-tetrachloro-dipivalato-diRe(III) complexes [83], which contain Re-Re quadruple bonds interacted with DNA, forming covalent interstrand cross-links and inducing DNA cleavage.…”

Section: Dna Effects Of Re Complexesmentioning

confidence: 99%

Design of Rhenium Compounds in Targeted Anticancer Therapeutics

Collery¹,

Desmaële

Veena

2019

CPD

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Background: Many rhenium (Re) complexes with potential anticancer properties have been synthesized in the recent years with the aim to overcome the clinical limitations of platinum agents. Re(I) tricarbonyl complexes are the most common but Re compounds with higher oxidation states have also been investigated, as well as hetero-metallic complexes and Re-loaded self-assembling devices. Many of these compounds display promising cytotoxic and phototoxic properties against malignant cells but all Re compounds are still at the stage of preclinical studies. Methods: The present review focused on the rhenium based cancer drugs that were in preclinical and clinical trials were examined critically. The detailed targeted interactions and experimental evidences of Re compounds reported by the patentable and non-patentable research findings used to write this review. Results: In the present review, we described the most recent and promising rhenium compounds focusing on their potential mechanism of action including, phototoxicity, DNA binding, mitochondrial effects, oxidative stress regulation or enzyme inhibition. Many ligands have been described that modulating the lipophilicity, the luminescent properties, the cellular uptake, the biodistribution, and the cytotoxicity, the pharmacological and toxicological profile. Conclusion: Re-based anticancer drugs can also be used in targeted therapies by coupling to a variety of biologically relevant targeting molecules. On the other hand, combination with conventional cytotoxic molecules, such as doxorubicin, allowed to take into profit the targeting properties of Re for example toward mitochondria. Through the example of the diseleno-Re complex, we showed that the main target could be the oxidative status, with a down-stream regulation of signaling pathways, and further on selective cell death of cancer cells versus normal cells.

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“…Recently, an Re I complex with extended -delocalized systems, namely cinnamoyl-like ligands, showed a significant binding affinity, which was corroborated by a high intrinsic binding constant and an apparent resistance to hydrolysis (Ismail et al, 2018). The archetypical phenanthroline with -conjugated rings interacts with DNA base pairs via van der Waals (vdW) stacking interactions (Ghosh et al, 2014). These studies led to an upsurge of interest in the structural chemistry of metal complexes in order to achieve a better understanding of the role of noncovalent intermolecular interactions, such as hydrogen bonding, electrostatic,stacking and n!…”

Section: Introductionmentioning

confidence: 99%

“…Simple ground-state absorption is commonly used to investigate intercalating binding modes and their strength in complexes of Re I and DNA (Ismail et al, 2018). The inherent hypochromic characteristic indicates the occurrence of metal complexes binding to the minor grooves of DNA through partial intercalation (Ghosh et al, 2014). With regard to molecular architecture, Re I tricarbonyl complexes have favourable structural entities with a propensity for DNA intercalation (Parson et al, 2014).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular structures of rhenium(I) complexes mediated by ligand planarity via the interplay of substituents

2018

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The crystal and molecular structures of two Re tricarbonyl complexes, namely fac-tricarbonylchlorido[1-(4-fluorocinnamoyl)-3-(pyridin-2-yl-κN)pyrazole-κN]rhenium(I), [ReCl(CHFNO)(CO)], (I), and fac-tricarbonylchlorido[1-(4-nitrocinnamoyl)-3-(pyridin-2-yl-κN)pyrazole-κN]rhenium(I) acetone monosolvate, [ReCl(CHClNO)(CO)]·CHO, (II), are reported. The complexes form centrosymmetric dimers that are linked into one-dimensional columns by C-H...Cl and N-O...H interactions in (I) and (II), respectively. C-H...Cl interactions in (II) generate two R(7) loops that merge into a single R(10) loop. These interactions involve the alkene, pyrazole and benzene rings, hence restricting the ligand rotation and giving rise to a planar conformation. Unlike (II), complex (I) exhibits a twisted conformation of the ligand and a pair of molecules forms a centrosymmetric dimer with an R(10) loop via C-H...O interactions. The unique supramolecular structures of (I) and (II) are determined by their planarity and weak interactions. The planar conformation of (II) provides a base for appreciable π-π stacking interactions compared to (I). In addition, an N-O...π interaction stabilizes the supramolecular structure of (II). We report herein the first n→π* interactions of Re tricarbonyl complexes, which account for 0.33 kJ mol. Intermolecular C-H...Cl and C-H...O interactions are present in both complexes, with (II) showing a greater preference for these interactions compared to (I), with cumulative contributions of 48.7 and 41.5%, respectively. The influence of inductive (fluoro) and/or resonance (nitro) effects on the π-stacking ability was further supported by LOLIPOP (localized orbital locator-integrated π over plane) analysis. The benzene ring of (II) demonstrated a higher π-stacking ability compared to that of (I), which is supported by the intrinsic planar geometry. The HOMA (harmonic oscillator model of aromaticity) index of (I) revealed more aromaticity with respect to (II), suggesting that NO greatly perturbed the aromaticity. The Hirshfeld fingerprint (FP) plots revealed the preference of (II) over (I) for π-π contacts, with contributions of 6.8 and 4.4%, respectively.

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Rhenium(II) nitrosyl complexes: synthesis, characterization, DFT calculations and DNA nuclease activity

Cited by 13 publications

References 65 publications

Biomimicking Oxidative Bromination and DNA Nuclease Activities of a New Structurally Characterised Oxido-Diperoxidomolybdenum(VI) Complex

Biomimicking Oxidative Bromination and DNA Nuclease Activities of a New Structurally Characterised Oxido-Diperoxidomolybdenum(VI) Complex

Design of Rhenium Compounds in Targeted Anticancer Therapeutics

Supramolecular structures of rhenium(I) complexes mediated by ligand planarity via the interplay of substituents

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