Synthesis, characterization, antiplasmodial evaluation and electrochemical studies of water-soluble heterobimetallic ferrocenyl complexes

Baartzes, Nadia; Stringer, Tameryn; Chellan, Prinessa; Combrinck, Jill M.; Smith, Peter J.; Hutton, Alan T.; Smith, Gregory S.

doi:10.1016/j.ica.2016.02.058

Cited by 7 publications

(5 citation statements)

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“…Mechanistic examination using the NP40-mediated β-hematin assay suggests disruption of the heme detoxification pathway as a possible mode of action. Before these studies, Rh(I)ClCp* congeners 57a and 58a exhibiting reversible redox character were investigated for their antiplasmodial effects on the CQS NF54 parasites along with their Ir(III)ClCp* ( 57b and 58b ) and Ru(II)Cl( p -cymene) ( 57c and 58c ) derivatives [ 23 , 61 ]. In both studies, the Rh(I)ClCp* complexes displayed comparable activities to the Ir(III)ClCp* and Ru(II)( p -cymene) derivatives, placing the rhodium metal as an attractive alternative to the extensively studied iridium and ruthenium metals for the generation of bioactive organometallic compounds.…”

Section: Rhodium Complexesmentioning

confidence: 99%

Recent Advances in the Biological Investigation of Organometallic Platinum-Group Metal (Ir, Ru, Rh, Os, Pd, Pt) Complexes as Antimalarial Agents

2020

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In the face of the recent pandemic and emergence of infectious diseases of viral origin, research on parasitic diseases such as malaria continues to remain critical and innovative methods are required to target the rising widespread resistance that renders conventional therapies unusable. The prolific use of auxiliary metallo-fragments has augmented the search for novel drug regimens in an attempt to combat rising resistance. The development of organometallic compounds (those containing metal-carbon bonds) as antimalarial drugs has been exemplified by the clinical development of ferroquine in the nascent field of Bioorganometallic Chemistry. With their inherent physicochemical properties, organometallic complexes can modulate the discipline of chemical biology by proffering different modes of action and targeting various enzymes. With the beneficiation of platinum group metals (PGMs) in mind, this review aims to describe recent studies on the antimalarial activity of PGM-based organometallic complexes. This review does not provide an exhaustive coverage of the literature but focusses on recent advances of bioorganometallic antimalarial drug leads, including a brief mention of recent trends comprising interactions with biomolecules such as heme and intracellular catalysis. This resource can be used in parallel with complementary reviews on metal-based complexes tested against malaria.

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Section: Rhodium Complexesmentioning

confidence: 99%

Recent Advances in the Biological Investigation of Organometallic Platinum-Group Metal (Ir, Ru, Rh, Os, Pd, Pt) Complexes as Antimalarial Agents

2020

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“…The Ru-complex (96) showed greater activity compared to both the Rh-complex (97) and Fc-containing sulfonated ligand (95). Neither of the studied molecules (95-98) inhibited the β-haematin formation at the tested concentration (100 μM), inferring that observed activities could be a result of an action on a different molecular target (Baartzes et al, 2016). The fact that several gold complexes possess antimalarial properties (Navarro et al, 1997) motivated Bjelosevic and coworkers (2012) to perform the synthesis of 1,2,1'substituted bis(diphenylphosphino)-Fc-and ruthenocenyl-gold(I) complexes (99, 100a-b and 101a-b; Fig.…”

Section: Fig 29mentioning

confidence: 87%

Recent updates in the development of mettallocenes with antimalarial activity

Aksic

Gencic

Radulović

2020

Facta Univ Phys Chem Technol

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Great progress in the fight against malaria has been made in the last decade. Nevertheless, the development of resistance to almost all commonly used antimalarial drugs poses a major threat to the sustainability of this progress and highlights the need for the discovery of novel potent and inexpensive antimalarials to stay one step ahead. After the finding of ferrocene-containing analog of chloroquine - ferroquine, that can overcome Plasmodium resistance, a ?big-bang? in the metallocene antimalarials research has occurred. This review describes in detail the most recent advances in this important field of medicinal chemistry. Even though it is quite hard to beat ferroquine, it seems that this could be succeeded by suitable modifications in the structure of ferroquine, by the introduction of ? second metal center or through joining metallocenes with two or more proven antimalarial motifs into a single molecule.

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“…132 also showed ca. [176] Interestingly, trioxane L41 (IC 50 = 225 nM) and trioxane dimer L42 (IC 50 = 34 nM) both showed decreased activity by ca. 4 and 3 times respectively.…”

Section: Antimalarial Activity Of 4 D Metal-based Complexesmentioning

confidence: 98%

“…In 2016, Smith et al took this idea of heterobimetallic complexes of ferrocene further by changing the N,O-type ligand slightly and using Ru(II)/Rh(III) as 2 nd metal centers instead of Rh(I) used by Stringer et al in 2015 (Figure 28). [176] The formed complexes 130 and 131 along with ferrocenyl L39 and N,O based ligand L37 were evaluated for their antimalarial efficiency against CQ-sensitive strain NF54 of P. falciparum where both the heterobimetallic complexes 130 and 131 along with ferrocene L40 showed moderate/low activity (IC 50 ca. 50 μM).…”

Section: Antimalarial Activity Of 4 D Metal-based Complexesmentioning

confidence: 99%

“…in 2015 (Figure 28). [176] The formed complexes 130 and 131 along with ferrocenyl L39 and N,O based ligand L37 were evaluated for their antimalarial efficiency against CQ‐sensitive strain NF54 of P. falciparum where both the heterobimetallic complexes 130 and 131 along with ferrocene L40 showed moderate/low activity (IC 50 ca . 50 μM).…”

Section: Antimalarial Activity Of 4 D Metal‐based Complexesmentioning

confidence: 99%

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Transition Metal Complexes as Antimalarial Agents: A Review

et al. 2023

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In antimalarial drug development research, overcoming drug resistance has been a major challenge for researchers. Nowadays, several drugs like chloroquine, mefloquine, sulfadoxine, and artemisinin are used to treat malaria. But increment in drug resistance has pushed researchers to find novel drugs to tackle drug resistance problems. The idea of using transition metal complexes with pharmacophores as ligands/ligand pendants to show enhanced antimalarial activity with a novel mechanism of action has gained significant attention recently. The advantages of metal complexes include tunable chemical/physical properties, redox activity, avoiding resistance factors, etc. Several recent reports have successfully demonstrated that the metal complexation of known organic antimalarial drugs can overcome drug resistance by showing enhanced activities than the parent drugs. This review has discussed the fruitful research works done in the past few years falling into this criterion. Based on transition metal series (3d, 4d, or 5d), the antimalarial metal complexes have been divided into three broad categories (3d, 4d, or 5d metal‐based), and their activities have been compared with the similar control complexes as well as the parent drugs. Furthermore, we have also commented on the potential issues and their possible solution for translating these metal‐based antimalarial complexes into the clinic.

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Synthesis, characterization, antiplasmodial evaluation and electrochemical studies of water-soluble heterobimetallic ferrocenyl complexes

Cited by 7 publications

References 23 publications

Recent Advances in the Biological Investigation of Organometallic Platinum-Group Metal (Ir, Ru, Rh, Os, Pd, Pt) Complexes as Antimalarial Agents

Recent Advances in the Biological Investigation of Organometallic Platinum-Group Metal (Ir, Ru, Rh, Os, Pd, Pt) Complexes as Antimalarial Agents

Recent updates in the development of mettallocenes with antimalarial activity

Transition Metal Complexes as Antimalarial Agents: A Review

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