Novel microwave synthesis of half‐sandwich [(η6‐C6H6)Ru] complexes and an evaluation of the biological activity and biochemical reactivity

Beckford, Floyd A.; Stott, Alyssa; González‐Sarrías, Antonio; Seeram, Navindra P.

doi:10.1002/aoc.3007

Cited by 13 publications

(5 citation statements)

References 31 publications

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“…This Ru-centered oxidation is irreversible even up to a scan rate of 500 mV s -1 . This pattern of behavior is similar to what we have observed for similar complexes bearing a p-cymene or benzene arene cap [6,7,30,35]. For such complexes E pa values range from 1.02 V to 1.11 V. Complex 3 had an irreversible oxidation at 0.91 V with an additional, though less defined peak, at 1.34 V.…”

Section: Synthesis and Characterizationsupporting

confidence: 86%

Anticancer, biophysical and computational investigations of half-sandwich ruthenium(II) thiosemicarbazone complexes: The effect of arene versus thiacrown face-cap

Beckford¹,

Stott²,

Mbarushimana³

et al. 2016

Interdiscip J Chem

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A series of half-sandwich ruthenium complexes, two containing an arene face-cap and the other a thiacrown ether face-cap were synthesized to investigate the necessity of the arene for anticancer activity in this class of compounds. The complexes are formulated as [(η 6 -p-cymene)Ru(dmabTSC)Cl]PF 6 , [(η 6 -benzene) Ru(dmabTSC)Cl]PF 6 (arene complexes), and [([9]aneS 3 (dmabTSC)Cl]PF 6 (dmabTSC = dimethylaminobenzaldehye thiosemicarbazone). It was observed that none of the complexes showed good anticancer activity in vitro against HCT-116 and Caco-2 (colon adenocarcinoma) cells. All three complexes can bind strongly to calfthymus DNA with binding constants on the order of 10 5 M -1 . In addition they all bind strongly to human serum albumin with binding constants between 10 5 and 10 6 M -1 . There appears to be a single binding site on the protein for these complexes. A computational investigation of these complexes and their hydrolysis products was carried out by molecular docking with DNA and topoisomerase II. From this analysis it is noted that the type of face-capping ligand had different effects on the two macromolecules. It is therefore noted that the knowledge gained from this study will be useful in identifying the type of complexes in this class that show useful metallodrug potential.

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Section: Synthesis and Characterizationsupporting

confidence: 86%

Anticancer, biophysical and computational investigations of half-sandwich ruthenium(II) thiosemicarbazone complexes: The effect of arene versus thiacrown face-cap

Beckford¹,

Stott²,

Mbarushimana³

et al. 2016

Interdiscip J Chem

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“…70,71 For RM175, anticancer activity towards several cell lines improved when administered in the presence of albumin, 72 highlighting the importance of such interactions for Ru-arene complexes. Indeed, previous Ru-arene antibacterial complexes with thiosemicarbazone ligands were observed to bind to HSA with strong affinity, 73 which was proportional to the observed antibacterial activity. 74 HSA contains a single tryptophan residue (Trp-214) which is responsible for the intrinsic fluorescence of the protein.…”

Section: Binding To Human Serum Albuminmentioning

confidence: 91%

A Ru(ii)-arene-ferrocene complex with promising antibacterial activity

et al. 2022

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“…As early as 2009, Floyd A. Beckford et al [ 70 , 127 , 128 ] designed and synthesized a series of 9-anthrachydrazones with N -substituted thiourea as side chains and used them as the active ligands to coordinate with Ru(II) through N / S -bidentate chelation. Benzene and p -cymene were used as Π-bonding co-ligands.…”

Section: The Anticancer Activity Studymentioning

confidence: 99%

“…Then, an organometallic Ru(II) complex with benzene as the Π-bonding co-ligand was synthesized by a novel microwave-assisted synthesis method. The side chain group of anthrahydrazone was thiourea or N -ethyl thiourea [ 128 ]. In previous studies, Ru(II) complexes with a N -ethyl thiourea side chain had the lowest activity, but the authors continued to select the Ru(II) complex replaced by N -ethyl, which may be related to its strong binding affinity with HSA/DNA and Topo II inhibition.…”

Section: The Anticancer Activity Studymentioning

confidence: 99%

“…The activity of the N -ethyl-substituted Ru(II) complex was 1~2 times that of the non-substituted Ru(II) complex. Furthermore, the anticancer activity of the Ru(II) complex against both cancer cells was also higher than that of the Ru(II) complex with the same side chain but with the co-ligand p -cymene, suggesting that the corresponding Ru(II) complex might have higher in vitro anticancer activity when there are no substituents on the benzene ring of the co-ligand [ 70 , 127 , 128 ].…”

Section: The Anticancer Activity Studymentioning

confidence: 99%

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Research Progress on the Biological Activities of Metal Complexes Bearing Polycyclic Aromatic Hydrazones

et al. 2022

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Due to the abundant and promising biological activities of aromatic hydrazones, it is of great significance to study the biological activities of their metal complexes for the research and development of metal-based drugs. In this review, we focus on the metal complexes of polycyclic aromatic hydrazones, which still do not receive much attention, and summarize the studies related to their biological activities. Although the large number of metal complexes in phenylhydrazone prevent them all from being summarized, the significant value of polycyclic aromatic hydrocarbons themselves (such as naphthalene and anthracene) as pharmacophores are also considered. Therefore, the bioactivities of the metal complexes of naphthylhydrazone and anthrahydrazone are focused on, and the recent research progress on the metal complexes of anthrahydrazone by the authors is also included. In terms of biological activities, these complexes mainly show antibacterial and anticancer activities, along with less bioactivities. The present review demonstrates that the structural design and bioactivities of these complexes are fundamental, which also indicates a certain structure—activity relationship (SAR) in some substructural areas. However, a systematic and comprehensive conclusion of the SAR is still not available, which suggests that more attention should be paid to the bioactivities of the metal complexes of polycyclic aromatic hydrazones since their potential in structural design and biological activity remains to be explored. We hope that this review will attract more researchers to devote their interest and energy into this promising area.

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Novel microwave synthesis of half‐sandwich [(η⁶‐C₆H₆)Ru] complexes and an evaluation of the biological activity and biochemical reactivity

Cited by 13 publications

References 31 publications

Anticancer, biophysical and computational investigations of half-sandwich ruthenium(II) thiosemicarbazone complexes: The effect of arene versus thiacrown face-cap

Anticancer, biophysical and computational investigations of half-sandwich ruthenium(II) thiosemicarbazone complexes: The effect of arene versus thiacrown face-cap

A Ru(ii)-arene-ferrocene complex with promising antibacterial activity

Research Progress on the Biological Activities of Metal Complexes Bearing Polycyclic Aromatic Hydrazones

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