Ru(II)‐<i>p</i>‐cymene Thiosemicarbazone Complexes as Inhibitors of Amyloid β (Aβ) Peptide Aggregation and Aβ‐Induced Cytotoxicity

Haribabu, Jebiti; Ranade, Dnyanesh S.; Bhuvanesh, Nattamai; Kulkarni, Purushottam; Karvembu, Ramasamy

doi:10.1002/slct.201702390

Cited by 26 publications

(24 citation statements)

References 69 publications

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“…To understand the effect of Fc moiety in catalysis, previously reported Ru(II)-pcymene complex containing indole TSC was employed as catalyst in the same reaction. [50] To our surprise, moderate activity i. e. 51 % selectivity of 3 a was observed compared to the present Fc-TSC complexes, inferring the synergistic effect between the Fc and Ru(II)-arene moieties.…”

Section: Synthesis Of 12-disubstituted Benzimidazolesmentioning

confidence: 47%

“…Then, the arene moiety was changed from p ‐cymene to benzene ( 5 ); Ru(II) complex with the former arene unit displayed better activity over its benzene counterpart (Figure 4). To understand the effect of Fc moiety in catalysis, previously reported Ru(II)‐ p ‐cymene complex containing indole TSC was employed as catalyst in the same reaction [50] . To our surprise, moderate activity i. e .…”

Section: Resultsmentioning

confidence: 80%

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Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Sindhuja

Bhuvanesh

et al. 2022

Eur J Inorg Chem

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The catalytic activity of Ru(II)-arene complexes containing ferrocene thiosemicarbazone (Fc-TSC) ligands was investigated towards the selective synthesis of 1,2-disubstituted benzimidazoles via acceptorless dehydrogenative coupling of diamines with primary alcohols. A series of Ru(II)-p-cymene complexes (1-4) containing Fc-TSC ligands (L 1 -L 4 ) were synthesized and characterized. From single crystal X-ray crystallographic studies, the molecular structures of L 3 and 4 were confirmed. The influence of electronic effect of ligands on the catalytic activity of their complexes was studied. The activity of good performer i. e. 4 was compared with that of its benzene counterpart (5). The catalysis was extended to aromatic, aliphatic and heterocyclic substituted primary alcohols, and phenylenediamines with electron-donating or -withdrawing substituents. Overall, synthesis of 1,2-disubstituted benzimidazoles was accomplished with good to moderate yields, with hydrogen and water as only by-products.

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Section: Synthesis Of 12-disubstituted Benzimidazolesmentioning

confidence: 47%

Section: Resultsmentioning

confidence: 80%

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Sindhuja

Bhuvanesh

et al. 2022

Eur J Inorg Chem

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“…Numerous biologically active molecules derived from natural sources contain a chromone moiety as their core. − These compounds have attracted the pharmaceutical industries to a large extent owing to their antioxidant, antitumor and antibacterial activities. − Besides these, several chromone derivatives have been used as antimicrobial, DNA-binding, DNA-cleavage, anticancer, antiallergic, neuroprotective, and pesticidal agents. − Although the appeal of chromones and their derivatives is widespread, the literature still lacks knowledge about their importance in coordination chemistry. Our group has been meticulously involved in studying the coordination behavior of heterocyclic TSCs with Ni(II), Cu(II), Zn(II), Pd(II), and Ru(II) and its influence on the biomolecular interactions and anticancer activity against various cancer and normal cell lines. − Most of these complexes induced cell death through apoptosis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Palladium(II) Complexes via Michael Addition: Antiproliferative Effects through ROS-Mediated Mitochondrial Apoptosis and Docking with SARS-CoV-2

et al. 2020

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Metal complexes have numerous applications in the current era, particularly in the field of pharmaceutical chemistry and catalysis. A novel synthetic approach for the same is always a beneficial addition to the literature. Henceforth, for the first time, we report the formation of three new Pd(II) complexes through the Michael addition pathway. Three chromone-based thiosemicarbazone ligands (SVSL1–SVSL3) and Pd(II) complexes ( 1 – 3 ) were synthesized and characterized by analytical and spectroscopic tools. The Michael addition pathway for the formation of complexes was confirmed by spectroscopic studies. Distorted square planar structure of complex 2 was confirmed by single-crystal X-ray diffraction. Complexes 1 – 3 were subjected to DNA- and BSA-binding studies. The complex with cyclohexyl substituent on the terminal N of thiosemicarbazone ( 3 ) showed the highest binding efficacy toward these biomolecules, which was further understood through molecular docking studies. The anticancer potential of these complexes was studied preliminarily by using MTT assay in cancer and normal cell lines along with the benchmark drugs (cisplatin, carboplatin, and gemcitabine). It was found that complex 3 was highly toxic toward MDA-MB-231 and AsPC-1 cancer cells with IC 50 values of 0.5 and 0.9 μM, respectively, and was more efficient than the standard drugs. The programmed cell death mechanism of the complexes in MDA-MB-231 cancer cells was confirmed. Furthermore, the complexes induced apoptosis via ROS-mediated mitochondrial signaling pathway. Conveniently, all the complexes showed less toxicity (≥50 μM) against MCF-10a normal cell line. Molecular docking studies were performed with VEGFR2, EGFR, and SARS-CoV-2 main protease to illustrate the binding efficiency of the complexes with these receptors. To our surprise, binding potential of the complexes with SARS-CoV-2 main protease was higher than that with chloroquine and hydroxychloroquine.

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“…Further, the complexes exhibited attenuation of Aβ induced cytotoxicity due to flexible alkyl substitution at terminal nitrogen of thiosemicarbazone moiety. [22] The anticancer activity of arene ruthenium complexes (Figure 2b) comprising (N,O)-attached ketoamine ligands with elevated IC 50 concentrations and a longer incubation period has been reported by Dyson et al In addition, the compounds displayed a stronger antivascular effect in the in vivo chicken chorioallantoic membrane model than RAPTA-C [23] Pettinari et al synthesized Ru (II)-areneacylpyrazolonato complexes (Figure 2c) and investigated their cytotoxicity with various cancer cells (MCF-7, HepG2, HeLa and HCT-116) with high IC 50 concentration. [24] Castonguay et al documented the anticancer activity of arene ruthenium complexes (Figure 2d) containing (N,O)-chelating Schiff base ligands on various cancerous and non-cancerous cells and demonstrated that ligand modification alters the biological activity of metal complexes.…”

Section: Introductionmentioning

confidence: 99%

Assessment of antiproliferative activity of new half‐sandwich arene Ru (II) furylbenzhydrazone complexes

Prabaharan

Ramesh

Umapathy

et al. 2021

Applied Organom Chemis

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The study attempts in finding an effective anticancer activity of six new arene ruthenium (II) complexes possessing the composition of [(η 6 -arene)Ru(L)Cl] (arene = benzene (1-3) /p-cymene (4-6); L = 2-furyl methyl benzhydrazones).Elemental analysis, Fourier transform infrared spectroscopy (FT-IR), UV-vis, nuclear magnetic resonance (NMR), and high resolution mass spectrometry (HR-MS) techniques were utilized to study the synthesized complexes. The single crystal X-ray crystallography validated the bidentate mode of coordination of the benzhydrazone ligand and pseudo-octahedral geometry around ruthenium ion. MTT assay has been performed to assess the in vitro growth of cancer cell inhibition ability of all the complexes against MCF-7(breast carcinoma), HuH-7 (hepatocellular carcinoma), and HeLa (cervical cancer), along with non-cancerous L132 (human lung epithelium) cell lines. It has been found that all the six complexes exhibit good to excellent cytotoxicity toward the cancer cell lines tested with low IC 50 values compared to cisplatin. Among the synthesized complexes, complex 6 shows potential cytotoxicity against all the cancer cell lines. The observed higher cytotoxicity of the complex 6 may be due to the electron donating methoxy group of the ligand and hydrophobic character of arene moiety. Eventually, the staining techniques such as AO-EB, HOECHST 33342, RH-123, and reactive oxygen species (ROS) establish that all the complexes bring about cell death via apoptosis. The present research results emphasize the more possibility to promote potential arene ruthenium anticancer agents.

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Ru(II)‐p‐cymene Thiosemicarbazone Complexes as Inhibitors of Amyloid β (Aβ) Peptide Aggregation and Aβ‐Induced Cytotoxicity

Cited by 26 publications

References 69 publications

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Synthesis of 1,2‐Disubstituted Benzimidazoles via Acceptorless Dehydrogenative Coupling Using Ru(II)‐Arene Catalysts Containing Ferrocene Thiosemicarbazone

Synthesis of Palladium(II) Complexes via Michael Addition: Antiproliferative Effects through ROS-Mediated Mitochondrial Apoptosis and Docking with SARS-CoV-2

Assessment of antiproliferative activity of new half‐sandwich arene Ru (II) furylbenzhydrazone complexes

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