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A series of the eight novel organoantimony(V) cyanoximates of Sb(C6H5)4L composition was synthesized using the high-yield heterogeneous metathesis reaction between solid AgL (or TlL) and Sb(C6H5)4Br in CH3CN at room temperature. Cyanoximes L were specially selected from a large group of 48 known compounds of this subclass of oximes on the basis of...
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Context 1
... (Figure 1) represent a new subclass of small organic molecules-oximes, the chemistry and applications of which have been intensely developed during the last two decades [14][15][16][17]. Cyanoximes and their metal salts and Werner-type complexes demonstrate a large spectrum of biological activity: pesticide antidotes [18,19], antimicrobial [20,21], and growth regulation in plants [22,23]. ...
Citations
... Previously, we synthesized and characterized a series of novel organoantimony(V) cyanoximates. These compounds, denoted by the general formula Sb(C 6 H 5 ) 4 L, with L representing the ligand, were obtained by subject ing AgL (or TlL) and Sb(C 6 H 5 ) 4 Br in CH 3 CN to high-yield heterogeneous metathesis at room temperature (28). The eight cyanoximate ligands used in our previous study belong to a new subclass of small organic molecules that are chemically and thermally stable (29) and non-cytotoxic (30)(31)(32) and exhibit a range of biological activities (33)(34)(35)(36)(37)(38). ...
... The eight cyanoximate ligands used in our previous study belong to a new subclass of small organic molecules that are chemically and thermally stable (29) and non-cytotoxic (30)(31)(32) and exhibit a range of biological activities (33)(34)(35)(36)(37)(38). When tested against a panel of drug-resistant bacterial and fungal species, including Gram-negative Escherichia coli and Pseudomonas aeruginosa, Gram-positive Staphylococ cus aureus, and fungal pathogens Cryptococcus neoformans and Candida albicans, these compounds varied in their antibacterial activity and showed promise as both broad-and narrow-spectrum antimicrobials (28,39). ...
... The two compounds SbPh 4 TCO and SbPh 4 TDCO did not show any antibacterial activity toward any of the tested pathogens. This lack of antibacterial activity of SbPh 4 TDCO differs from our previous results that were based on disc diffusion assays and where the compound showed a growth inhibitory effect against S. aureus (28). It is possible that the poor solubility of the drug in liquid medium prevents its activity. ...
Antimicrobial resistance (AMR) poses a significant worldwide public health crisis that continues to threaten our ability to successfully treat bacterial infections. With the decline in effectiveness of conventional antimicrobial therapies and the lack of new antibiotic pipelines, there is a renewed interest in exploring the potential of metal-based antimicrobial compounds. Antimony-based compounds with a long history of use in medicine have re-emerged as potential antimicrobial agents. We previously synthesized a series of novel organoantimony(V) compounds complexed with cyanoximates with a strong potential of antimicrobial activity against several AMR bacterial and fungal pathogens. Here, five selected compounds were studied for their antibacterial efficacy against three important bacterial pathogens: Pseudomonas aeruginosa, Escherichia coli, and Staphylococcus aureus. Among five tested compounds, SbPh4ACO showed antimicrobial activity against all three bacterial strains with the MIC of 50–100 µg/mL. The minimum bactericidal concentration/MIC values were less than or equal to 4 indicating that the effects of SbPh4ACO are bactericidal. Moreover, ultra-thin electron microscopy revealed that SbPh4ACO treatment caused membrane disruption in all three strains, which was further validated by increased membrane permeability. We also showed that SbPh4ACO acted synergistically with the antibiotics, polymyxin B and cefoxitin used to treat AMR strains of P. aeruginosa and S. aureus, respectively, and that at synergistic MIC concentration 12.5 µg/mL, its cytotoxicity against the cell lines, Hela, McCoy, and A549 dropped below the threshold. Overall, the results highlight the antimicrobial potential of novel antimony-based compound, SbPh4ACO, and its use as a potentiator of other antibiotics against both Gram-positive and Gram-negative bacterial pathogens.
IMPORTANCE
Antibiotic resistance presents a critical global public health crisis that threatens our ability to combat bacterial infections. In light of the declining efficacy of traditional antibiotics, the use of alternative solutions, such as metal-based antimicrobial compounds, has gained renewed interest. Based on the previously synthesized innovative organoantimony(V) compounds, we selected and further characterized the antibacterial efficacy of five of them against three important Gram-positive and Gram-negative bacterial pathogens. Among these compounds, SbPh4ACO showed broad-spectrum bactericidal activity, with membrane-disrupting effects against all three pathogens. Furthermore, we revealed the synergistic potential of SbPh4ACO when combined with antibiotics, such as cefoxitin, at concentrations that exert no cytotoxic effects tested on three mammalian cell lines. This study offers the first report on the mechanisms of action of novel antimony-based antimicrobial and presents the therapeutic potential of SbPh4ACO in combating both Gram-positive and Gram-negative bacterial pathogens while enhancing the efficacy of existing antibiotics.
... Hydrogen-bonded frameworks based on (ccnm) À and appropriate hydrogen-bond-donor organic cations offer attractive paradigms for the crystal engineering and biology of conjugated methanide-type anions. In particular, the structural trends of these systems may be applicable to such issues of (ccnm) À chemistry as solvatochromism and the behaviour of the anion as a component of ionic liquids (Janikowski et al., 2012) and non-antibiotic antimicrobials (Gerasimchuk et al., 2007(Gerasimchuk et al., , 2022. ...
Developing the structures of organic materials that rely on the hydrogen bonding of multifunctional substrates is often complicated due to a competition between various possible motifs. In this context, the illustrative case of the carbamoylcyanonitrosomethanide anion, [ONC(CN)–C(O)NH2]⁻, suggests sufficient control over the crystal lattice with a set of supramolecular synthons, which are specific to all the present nitroso, carbamoyl and cyano groups. The structures of the carbamoylcyanonitrosomethanide salts of ethane-1,2-diammonium, C2H10N2²⁺·2C3H2N3O2⁻, (1), piperazine-1,4-diium, C4H12N2²⁺·2C3H2N3O2⁻, (2), butane-1,4-diammonium, C4H14N2²⁺·2C3H2N3O2⁻, (3), and hexane-1,6-diammonium, C6H18N2²⁺·2C3H2N3O2⁻, (4), reveal two- and three-dimensional hydrogen-bonded frameworks governed by a set of site-selective interactions. The strongest N—H⋯O hydrogen bonds [N⋯O = 2.6842 (17)–2.8718 (17) Å, mean 2.776 (2) Å] are associated with the polarized ammonium N—H donors and nitroso O-atom acceptors, which sustain invariant motifs in the form of nitroso/ammonium dimers. Subtle structural changes within this series of compounds concern the rupture of some weaker interactions, i.e. mutual hydrogen bonds of the carbamoyl groups in (1)–(3) [N⋯O = 2.910 (2)–2.9909 (18) Å; mean 2.950 (2) Å] and carbamoyl/nitrile hydrogen bonds in (1), (2) and (4) [N⋯N = 2.936 (2)–3.003 (3) Å, mean 2.977 (2) Å], providing a gradual evolution of the hydrogen-bonding pattern. A hierarchy of the synthons involving three different groups could be applicable to supramolecular synthesis with polyfunctional methanide species, suggesting also a degree of control over layered and interpenetrated hydrogen-bonded networks.
The mounting burden of antimicrobial resistance (AMR) is one of the most concerning threats to public health worldwide. With low economic incentives and a dwindling supply of new drugs in clinical pipelines, more innovative approaches to novel drug design and development are desperately required. Metal-based compounds are rapidly emerging as an alternative to organic drugs, as they have the ability to kill pathogens via metal-specific modes of action. We herein review recent advances in metal-based antibacterial agents, including metal complexes, metal ions and catalytic metallodrugs. The review concludes with a perspective on the rational design of metal-based antibiotics, and how we can exploit their unique properties to tackle AMR.
