Synthesis, characterization and antimicrobial evaluation of mono- and polynuclear ferrocenyl-derived amino and imino complexes

Baartzes, Nadia; Stringer, Tameryn; Seldon, Ronnett; Warner, Digby F.; Kock, Carmen de; Smith, Peter J.; Smith, Gregory S.

doi:10.1016/j.jorganchem.2016.02.033

Cited by 12 publications

(12 citation statements)

References 32 publications

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“…A series of monomeric (6)(7)(8)(15)(16), dimeric (9-11) and trimeric (12)(13)(14) ferrocenyl quinoline complexes were prepared. All the compounds were characterised by a range of analytical and spectroscopic techniques.…”

Section: Discussionmentioning

confidence: 99%

“…The synthesised compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16) were screened against the metronidazole-sensitive G3 strain of T. vaginalis at either 50 or 100 µM concentrations. The data obtained for this study are presented in Fig.…”

Section: β-Haematin Inhibition Studiesmentioning

confidence: 99%

“…In most cases (with the exception of 12), compounds that possess the salicylaldimine or salicylaldamine moieties exhibit enhanced activity compared to the other derivatives. The amines (13)(14)(15)(16) (Table 5) to metronidazole but the data does show that incorporation of ferrocene as part of these systems can lead to enhanced activity. This is consistent with data observed in a previous study.…”

Section: β-Haematin Inhibition Studiesmentioning

confidence: 99%

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Mono- and multimeric ferrocene congeners of quinoline-based polyamines as potential antiparasitics

et al. 2016

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A series of mono- and multimeric polyamine-containing ferrocenyl complexes containing a quinoline motif were prepared. The complexes were characterised by standard techniques. The molecular structure of the monomeric salicylaldimine derivative was elucidated using single crystal X-ray diffraction and was consistent with the proposed structure. The antiplasmodial activity of the compounds were evaluated in vitro against both the NF54 (chloroquine-sensitive) and K1 (chloroquine-resistant) strains of Plasmodium falciparum. The polyamine derivatives exhibit good resistance index values suggesting that these systems are beneficial in overcoming the resistance experienced by chloroquine. Mechanistic studies suggest that haemozoin formation may be the target of these quinoline complexes in the parasite. Some of the complexes exhibit moderate to high cytotoxicity against WHCO1 oesophageal cancer cells in vitro. The monomeric ferrocenyl-amine complexes exhibit potent activity against this particular cell line. The complexes were also screened against the G3 strain of Trichomonas vaginalis and the salicylaldimine complexes demonstrated promising activity at the tested concentration. All of these compounds show no inhibitory effect on several common normal flora bacteria, indicative of their selectivity for eukaryotic pathogens and cancer.

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Section: Discussionmentioning

confidence: 99%

Section: β-Haematin Inhibition Studiesmentioning

confidence: 99%

Section: β-Haematin Inhibition Studiesmentioning

confidence: 99%

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Mono- and multimeric ferrocene congeners of quinoline-based polyamines as potential antiparasitics

et al. 2016

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“…Two metallodendrimers (Cu(II) and Zn(II) ions) based on PAMAM scaffolds modified with 1,8-naphthalimide moieties were synthesized, characterized, and screened in vitro against six pathogenic bacteria and two strains of yeasts as model. Strains such as Gram-positive Sarcina lutea, Bacillus cereus, and Bacillus subtilis and, Gram-negative strains Escherichia coli, Pseudomonas aeruginosa, and Acinetobacter johnsonii (antibacterial activity), and the yeasts F I G U R E 1 5 Octameric TF dendrimer using a novel route for SPPS of glycopeptide dendrimer synthesis involving an interesting N-alkylcysteine (NAC) assisted thioesterification through a powerful N-to S-acyl migration following quenching with excess mercaptopropionic acid intermediate Ferrocenyl metallodendrimers (Baartzes et al, 2016(Baartzes et al, , 2018.…”

Section: Metallodendrimers: An Additional Nanostrategy To Fight Cancermentioning

confidence: 99%

Aberrant glycosylation patterns on cancer cells: Therapeutic opportunities for glycodendrimers/metallodendrimers oncology

Moffett

Shiao

Mousavifar

et al. 2020

WIREs Nanomed Nanobiotechnol

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Despite exciting discoveries and progresses in drug design against cancer, its cure is still rather elusive and remains one of the humanities major challenges in health care. The safety profiles of common small molecule anti‐cancer therapeutics are less than at acceptable levels and limiting deleterious side‐effects have to be urgently addressed. This is mainly caused by their incapacity to differentiate healthy cells from cancer cells; hence, the use of high dosage becomes necessary. One possible solution to improve the therapeutic windows of anti‐cancer agents undoubtedly resides in modern nanotechnology. This review presents a discussion concerning multivalent carbohydrate–protein interactions as this topic pertains to the fundamental aspects that lead glycoscientists to tackle glyconanoparticles. The second section describes the detailed properties of cancer cells and how their aberrant glycan surfaces differ from those of healthy cells. The third section briefly describes the immune systems, both innate and adaptative, because the numerous displays of cell surface protein receptors necessitate to be addressed from the multivalent angles, a strength full characteristic of nanoparticles. The next chapter presents recent advances in glyconanotechnologies, including glycodendrimers in particular, as they apply to glycobiology and carbohydrate‐based cancer vaccines. This was followed by an overview of metallodendrimers and how this rapidly evolving field may contribute to our arsenal of therapeutic tools to fight cancer. This article is categorized under: Therapeutic Approaches and Drug Discovery > Emerging Technologies Nanotechnology Approaches to Biology > Nanoscale Systems in Biology Therapeutic Approaches and Drug Discovery > Nanomedicine for Oncologic Disease

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“…[1][2][3] One of the key building blocks for incorporation of a ferrocene moiety into target structures is vinylferrocene. Vinylferrocene has been used in organic synthesis in Heck type reactions [4][5][6][7][8][9] and Diels-Alder cycloadditions. 10,11 During our research on new syntheses of chiral ferrocene derivatives, we needed access to vinylferrocene in larger quantities.…”

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confidence: 99%

A Practical Three-Step Synthesis of Vinylferrocene

2017

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Synthesis, characterization and antimicrobial evaluation of mono- and polynuclear ferrocenyl-derived amino and imino complexes

Cited by 12 publications

References 32 publications

Mono- and multimeric ferrocene congeners of quinoline-based polyamines as potential antiparasitics

Mono- and multimeric ferrocene congeners of quinoline-based polyamines as potential antiparasitics

Aberrant glycosylation patterns on cancer cells: Therapeutic opportunities for glycodendrimers/metallodendrimers oncology

A Practical Three-Step Synthesis of Vinylferrocene

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