Correction: Ferrocene-appended pharmacophores: an exciting approach for modulating the biological potential of organic scaffolds

Singh, Amandeep; Lumb, Isha; Mehra, Vishu; Kumar, Vipan

doi:10.1039/c9dt90027f

Cited by 5 publications

(8 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this work, the ferrocene molecule, one active compound with low levels of in vivo toxicity, was coupled in N-terminus of the peptide RP1 aiming to obtain a more active compound (Fc-RP1). Previous studies showed that compounds conjugated with organometallics, like ferrocene, has great biological potential [38,40,52,[70][71][72][73].…”

Section: Plos Onementioning

confidence: 99%

“…However, the Fc-RP1 conjugated showed higher toxicity (17.3 μmol L -1 ) when in contact with macrophage as compared with the same tests for RP1 peptide and ferrocene carboxylic acid molecule (>100 μmol L -1 ). It is well-known that bioconjugates containing organometallic compounds such as the ferrocene have great biological potential [40,64,71,73]. It is also assumed that this compound acts in the generation of reactive oxygen species.…”

Section: Plos Onementioning

confidence: 99%

“…The development of new drugs through the synthesis of bioconjugates containing organic molecules such as ferrocene, has been increasing due to its biological potential. Ferrocene is a low cost organometallic molecule that shows low toxicity and reversible redox properties, its ability to modify the structure by replacing the aryl/heteroaryl nucleus with the ferrocene in an organic molecule confers a significant change in molecular properties such as solubility and hydro/lipophilicity, enabling biological action of bioconjugates derived from this compound [40].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Antimicrobial activity of RP-1 peptide conjugate with ferrocene group

et al. 2020

View full text Add to dashboard Cite

Parasitic diseases are a neglected and serious problem, especially in underdeveloped countries. Among the major parasitic diseases, Leishmaniasis figures as an urgent challenge due to its high incidence and severity. At the same time, the indiscriminate use of antibiotics by the population is increasing together with resistance to medicines. To address this problem, new antibiotic-like molecules that directly kill or inhibit the growth of microorganisms are necessary, where antimicrobial peptides (AMPs) can be of great help. In this work, the ferrocene molecule, one active compound with low levels of in vivo toxicity, was coupled to the N-terminus of the RP1 peptide (derived from the human chemokine CXCL4), aiming to evaluate how this change modifies the structure, biological activity, and toxicity of the peptide. The peptide and the conjugate were synthesized using the solid phase peptide synthesis (SPPS). Circular dichroism assays in PBS showed that the RP1 peptide and its conjugate had a typical spectrum for disordered structures. The Fc-RP1 presented antiamastigote activity against Leishmania amazonensis (IC 50 = 0.25 μmol L -1 ). In comparison with amphotericin B, a second-line drug approved for leishmaniasis treatment, (IC 50 = 0.63 μmol L -1 ), Fc-RP1 was more active and showed a 2.5-fold higher selectivity index. The RP1 peptide presented a MIC of 4.3 μmol L -1 against S. agalactiae, whilst Fc-RP1 was four times more active (MIC = 0.96 μmol L -1 ), indicating that ferrocene improved the antimicrobial activity against Gram-positive bacteria. The Fc-RP1 peptide also decreased the minimum inhibitory concentration (MIC) in the assays against E. faecalis (MIC = 7.9 μmol L -1 ), E. coli (MIC = 3.9 μmol L -1 ) and S. aureus (MIC = 3.9 μmol L -1 ). The cytotoxicity of the compounds was tested against HaCaT cells, and no significant activity at the highest concentration tested (500 μg. mL -1 ) was observed, showing the high potential of this new compound as a possible new drug. The coupling of ferrocene also increased the vesicle permeabilization of the peptide, showing a direct relation between high peptide concentration and high carboxyfluorescein release, which indicates the action mechanism by pore formation on the vesicles. Several studies have shown that ferrocene destabilizes cell membranes through lipid peroxidation, leading to cell lysis. It is noteworthy that the Fc-RP1 peptide synthesized here PLOS ONE

show abstract

Section: Plos Onementioning

confidence: 99%

Section: Plos Onementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Antimicrobial activity of RP-1 peptide conjugate with ferrocene group

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The coupling constant J is reported in hertz (Hz). 1 H-and 13 C-NMR peaks were assigned based on the combined analysis of a series of 1 H-1 H (COSY) and 1 H-13 C (HSQC, HMBC) correlation spectra.…”

Section: Generalmentioning

confidence: 99%

“…The use of ferrocene building blocks in medicinal chemistry is an intriguing research area. Apart from its anticancer, antibacterial, antifungal, and antiparasitic potential [1], the ferrocenyl moiety has been increasingly used in drug design [2]. In particular, the bioisosteric replacement of a phenyl ring or heteroaromatic with the ferrocenyl group can lead to compounds with enhanced potency and/or selectivity, compared with the parent, purely organic molecule [3].…”

Section: Introductionmentioning

confidence: 99%

O-((Ferrocenyl)(3-fluorophenyl)methyl)hydroxylamine

Foscolos

Γεωργίου

Papadopoulos

et al. 2022

Molbank

View full text Add to dashboard Cite

Based on the diaryl hydroxylamine scaffold, which exhibits the potential to inhibit all three enzymes of the first step of the kynurenine pathway, the main tryptophan degradation pathway in mammals, which is often activated in cancer, we report herein the synthesis of a ferrocenyl analogue as an attempt to improve the scaffold’s pan-inhibitory potency through the isosteric replacement of a phenyl group with the ferrocenyl moiety. The synthetic methodology followed gives access to O-((ferrocenyl)(aryl)methyl)hydroxylamines, a class of compounds not yet reported in the literature.

show abstract