Single crystal, DNA interaction and cytotoxicity studies of rhenium(I) organometallic compounds

Varma, Reena R.; Pursuwani, Bharat H.; Suresh, Eringathodi; Bhatt, Bhupesh S.; Patel, Mohan N.

doi:10.1016/j.molstruc.2019.127068

Cited by 20 publications

(12 citation statements)

References 48 publications

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“…2. The 1 H and 13 C NMR spectra are shown in supplementary material 1. incubated for 16-18 h. Next day, the treated cells were collected by centrifugation at 10,000 rpm for 10 min and were dissolved in 500 mL of PBS. The 80 mL of yeast culture dissolved in PBS and 20 mL of 0.4% trypan blue prepared in PBS were mixed, and cells were observed in a compound microscope (40X).…”

Section: General Methods For Synthesis Of 135-trisubstituted Pyrazole Ligands (L 1 -L 6 )mentioning

confidence: 99%

“…These all encouraged us to synthesize compounds containing bis-heterocyclic imidazole-pyrazoline moiety that chelated with the rhenium metal and evaluate their anti-yeast and anti-cancer activity. In continuation of our earlier work [13], in this study, our main focus is to enhance the anticancer activity of rhenium(I) complexes, DNA-binding a nities of synthesized compounds and imperative changes in some related properties. Thoughtful features that contribute to the recognition of DNA by metal based drugs or small molecules is crucial for the enhancement of drugs targeted at DNA.…”

Section: Introductionmentioning

confidence: 98%

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Biomolecular Interaction, Antibacterial and Anticancer Activities of Organometallic Re(I) Complexes with 5-(2-butyl-5-chloro-1H-imidazol-4-yl)-1,3-diaryl-4,5-dihydro-1H-pyrazole

Varma

Pandya

Vaidya

et al. 2021

Preprint

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Organometallic rhenium(I) complexes (I-VI) using substituted 5-(2-butyl-5-chloro-1H-imidazol-4-yl)-1,3-diaryl-4,5-dihydro-1H-pyrazole have been synthesized and characterised by spectroscopic method. For evaluation of HOMO-LUMO energy gap, estimation of bond angle, bond length data and Mulliken charge analysis DFT studies were performed. The complexes (I-VI) can be generated by bis-heterocyclic ligand followed by metal chelation. The interactions between synthesised compounds and double stranded DNA (HS DNA) was carried out by viscosity measurements, absorption titration, and gel electrophoresis gives information about modes of binding and the nucleolytic efficiency of compounds. Groove binding was suggested as the most possible mode and the DNA-binding (Kb) constants of the complexes were calculated. Electronic spectra and conductivity measurement confirm the different transition, and non-electrolytic nature of the metal complexes. Thermodynamic parameter ΔG0 value ranging from -7227.0 to -9463.0 J/moleoK. According to the thermodynamic parameter, the main binding force could be judged. In vivo and In vitro cytotoxicity against the eukaryotic and prokaryotic cells gives toxic nature of the synthesised compounds. An antimicrobial study was carried out by estimating MIC (Minimum Inhibitory Concentration) against two Gram-positive and three Gram-negative bacteria. All compounds found effective against S. cerevisiae which is confirmed by enhancing ROS production and DNA damage show by gel electrophoresis as compared to untreated yeast cell culture and DMSO.

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Section: General Methods For Synthesis Of 135-trisubstituted Pyrazole Ligands (L 1 -L 6 )mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Biomolecular Interaction, Antibacterial and Anticancer Activities of Organometallic Re(I) Complexes with 5-(2-butyl-5-chloro-1H-imidazol-4-yl)-1,3-diaryl-4,5-dihydro-1H-pyrazole

Varma

Pandya

Vaidya

et al. 2021

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“…: 272.31g/ mol; Empirical formula: General synthesis of complexes: The metal carbonyl complexes (I-VI) were synthesized using pentacarbonyl chloro rhenium(I) and ligands (L 1 -L 6 ) in ethanol in a 1:1 proportion. 16 Synthesis of [Re(CO) 3 the compounds. 19 The extent of inhibition is displayed as an IC 50 value, which is defined as the concentration required to inhibit cell growth to half.…”

Section: General Methods For Synthesis Of Pyrazolo[15-a]pyrimidines Lmentioning

confidence: 99%

“…13 C-APT data of ligands L 1 -L 6 and complexes I-VI show signals at 97-160 δ ppm confirm the presence of aromatic environment. 16 The crystal structure of Re(CO) 5 Cl show four CO at equatorial position, and one CO along with Cl atom at axial position. 28 The heterocyclic bidentate ligand approach from equatorial position and replace two CO molecules to form Re(I) complexes.…”

Section: Biological Activitiesmentioning

confidence: 99%

Synthesis, Characterization and Biological Application of Pyrazolo[1,5-a]pyrimidine Based Organometallic Re(I) Complexes

Varma¹,

Pandya²,

Vaidya³

et al. 2020

ACSi

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The neutral rhenium(I) complexes (I-VI) of type [ReCl(CO) 3 L n ] {where L 1 = 7-phenyl-5-(pyridin-2-yl)pyrazolo[1,5-a] pyrimidine, L 2 = 7-(4-bromophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimi-dine, L 3 = 7-(4-chlorophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L 4 = 7-(2-chlorophenyl)-5-(pyridin-2-yl)pyrazolo[1,5-a]pyrimidine, L 5 = 7-(4-methoxyphenyl)-5-(pyridin-2-yl)pyrazolo [1,5-a]pyrimidine, L 6 = 5-(pyridin-2-yl)-7-(p-tolyl)pyrazolo[1,5-a]py-rimidine} were synthesized and characterized by 13 C-APT, 1 H-NMR, IR, electronic spectra, magnetic moment and conductance measurement. The anti-proliferative activity on HCT116 cells by MTT assay suggests potent cytotoxic nature of complexes, some complexes even have better activity than standard drug cisplatin, oxaliplatin, and carboplatin. The complexes were found to have better antimicrobial activity compare to pyrazolo pyrimidine ligands. The theoretical study of compounds-DNA interactions was examined by molecular docking as a supportive tool to the experimental data, which suggests the groove mode of binding. The values of docking energy for compounds-DNA interaction were found in the range of-230.31 to-288.34 kJ/mol. The intrinsic binding constant values of complexes (1.1-3.5 × 10 5 M-1) were found higher than the ligands (0.32-1.8 × 10 5 M-1).

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“…+ are shown to bind to nucleobases and double stranded (ds) DNA 57,[123][124][125][126][127][128][129][130]. Therefore, we probed next the reactivity of the complexes with ds lambda bacteriophage DNA (λ-DNA) and the model nucleobases adenine and guanine.…”

mentioning

confidence: 99%

Highly Potent Rhenium(I) Tricarbonyl Complexes with Dual Anticancer and Anti-Angiogenic Activity Against Colorectal Carcinoma

Delasoie¹,

Pavić²,

Voutier³

et al. 2020

Preprint

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Synthesized and characterized a series of rhenium(I) trycarbonyl-based complexes with increased lipophilicity. Two of these novel compounds were discovered to possess remarkable anticancer, anti-angiogenic and antimetastatic activity <i>in vivo</i> (zebrafish-human CRC xenograft model), being effective at very low doses (1-3 µM). At doses as high as 250 µM the complexes did not provoke toxicity issues encountered in clinical anticancer drugs (cardio-, hepato-, and myelotoxicity). The two compounds exceed the antiproliferative and anti-angiogenic potency of clinical drugs cisplatin and sunitinib-malate, and display a large therapeutic window.

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Single crystal, DNA interaction and cytotoxicity studies of rhenium(I) organometallic compounds

Cited by 20 publications

References 48 publications

Biomolecular Interaction, Antibacterial and Anticancer Activities of Organometallic Re(I) Complexes with 5-(2-butyl-5-chloro-1H-imidazol-4-yl)-1,3-diaryl-4,5-dihydro-1H-pyrazole

Biomolecular Interaction, Antibacterial and Anticancer Activities of Organometallic Re(I) Complexes with 5-(2-butyl-5-chloro-1H-imidazol-4-yl)-1,3-diaryl-4,5-dihydro-1H-pyrazole

Synthesis, Characterization and Biological Application of Pyrazolo[1,5-a]pyrimidine Based Organometallic Re(I) Complexes

Highly Potent Rhenium(I) Tricarbonyl Complexes with Dual Anticancer and Anti-Angiogenic Activity Against Colorectal Carcinoma

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