Synthesis, characterization and pharmacological evaluation of ferrocenyl azines and their rhodium(I) complexes

Stringer, Tameryn; Guzgay, Hajira; Combrinck, Jill M.; Hopper, Melissa; Hendricks, Denver T.; Smith, Peter J.; Land, Kirkwood M.; Egan, Timothy J.; Smith, Gregory S.

doi:10.1016/j.jorganchem.2015.04.009

Cited by 28 publications

(12 citation statements)

References 56 publications

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“…and CQR K1 P. falciparum strains ( Figure 14) [60]. The complexes showed antiplasmodial activities in the low micromolar range against both strains and low resistance indices for 55b-c (RI = 0.22-0.85).…”

Section: Salicylaldiminato Ligandsmentioning

confidence: 98%

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: Salicylaldiminato Ligandsmentioning

confidence: 98%

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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“…Chem., 2016, 69, 51-66, <http://journals.sabinet.co.za/sajchem/>. reviewed by P. Barbaro et al 43 and A. Fihri et al 44 Potential uses of ferrocenylpyridines Schiff bases includes synthesis of materials for usage in electrochemical sensors, 45 homogenous catalysis, 46 cytotoxic agents, 16 antimicrobial compounds, [47][48][49] antiparasitic, 50 liquid crystals, 51 non-linear optical materials, 52 luminescent systems, 53 as well as coordination of a variety of metal centres to yield novel bimetallic complexes with fascinating architectures, 54,55 organometallic polymers 56 and conducting polymers. 57 In view of the aforementioned potential applications of ferrocenylpyridines and ferrocene derived Schiff bases, we have prepared a series of novel mono-substituted ferrocenyl-N-(pyridinylmethylene)anilines Schiff bases and their corresponding ferrocenyl-N-(pyridinylmethyl)anilines secondary amines.…”

Section: 36mentioning

confidence: 99%

Synthesis, physical and antimicrobial studies of ferrocenyl-N-(pyridinylmethylene)anilines and ferrocenyl-N-(pyridinylmethyl)anilines

2016

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“…[24] The basic ferrocenyl CH 2 NMe 2 moiety is known to enhance the antiplasmodial activity of ferrocene-based compounds. [23][24][25] Thus, it was considered prudent to synthesize both α-aminocresol analogues endowed with and devoid of this functionality to provide insights into the pharmacological effects of modifying the ferrocene unit on the biological activity of the resultant compounds. To avoid possible formation of the benzoxazine product, the target ferrocenyl α-aminocresol derivatives were assembled by reductive amination of substituted benzaldehydes (10 a-h) with ferrocenyl amines 7 a-b using sodium borohydride as the reductant to exclusively yield the desired products.…”

Section: Synthesismentioning

confidence: 99%

The in Vitro Antiplasmodial and Antiproliferative Activity of New Ferrocene‐Based α‐Aminocresols Targeting Hemozoin Inhibition and DNA Interaction

et al. 2020

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The conjugation of organometallic complexes to known bioactive organic frameworks is a proven strategy revered for devising new drug molecules with novel modes of action. This approach holds great promise for the generation of potent drug leads in the quest for therapeutic chemotypes with the potential to overcome the development of clinical resistance. Herein, we present the in vitro antiplasmodial and antiproliferative investigation of ferrocenyl α‐aminocresol conjugates assembled by amalgamation of the organometallic ferrocene unit and an α‐aminocresol scaffold possessing antimalarial activity. The compounds pursued in the study exhibited higher toxicity towards the chemosensitive (3D7) and ‐resistant (Dd2) strains of the Plasmodium falciparum parasite than to the human HCC70 triple‐negative breast cancer cell line. Indication of cross‐resistance was absent for the compounds evaluated against the multi‐resistant Dd2 strain. Structure‐activity analysis revealed that the phenolic hydroxy group and rotatable σ bond between the α‐carbon and NH group of the α‐amino‐o‐cresol skeleton are crucial for the biological activity of the compounds. Spectrophotometric techniques and in silico docking simulations performed on selected derivatives suggest that the compounds show a dual mode of action involving hemozoin inhibition and DNA interaction via minor‐groove binding. Lastly, compound 9 a, identified as a possible lead, exhibited preferential binding for the plasmodial DNA isolated from 3D7 P. falciparum trophozoites over the mammalian calf thymus DNA, thereby substantiating the enhanced antiplasmodial activity of the compounds. The presented research demonstrates the strategy of incorporating organometallic complexes into known biologically active organic scaffolds as a viable avenue to fashion novel multimodal compounds with potential to counter the development drug resistance.

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Synthesis, characterization and pharmacological evaluation of ferrocenyl azines and their rhodium(I) complexes

Cited by 28 publications

References 56 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

Synthesis, physical and antimicrobial studies of ferrocenyl-N-(pyridinylmethylene)anilines and ferrocenyl-N-(pyridinylmethyl)anilines

The in Vitro Antiplasmodial and Antiproliferative Activity of New Ferrocene‐Based α‐Aminocresols Targeting Hemozoin Inhibition and DNA Interaction

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