Syntheses, characterization and antifungal activity of novel dimethylbis(N-R-sulfonyldithiocarbimato)stannate(IV) complexes

Filho, Lucius F.O. Bomfim; Oliveira, Marcelo R. L.; Miranda, Liany Divina Lima; Vidigal, Antonio E. C.; Guilardi, Silvana; Souza, Rafael Aparecido Carvalho; Ellena, Javier; Ardisson, José D.; Zambolim, Laércio; Rubinger, Mayura M. M.

doi:10.1016/j.molstruc.2016.08.084

Cited by 11 publications

(2 citation statements)

References 26 publications

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“…The antifungal activity of metal compounds has been investigated even less than their antibacterial properties. ,,− Figure presents an overview of selected metal compounds with measured antifungal activity. Gasser and coworkers recently published an expansive review of the metal-based antifungals research field .…”

Section: Introductionmentioning

confidence: 99%

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Frei

Elliott

Kan

et al. 2022

JACS Au

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There are currently fewer than 10 antifungal drugs in clinical development, but new fungal strains that are resistant to most current antifungals are spreading rapidly across the world. To prevent a second resistance crisis, new classes of antifungal drugs are urgently needed. Metal complexes have proven to be promising candidates for novel antibiotics, but so far, few compounds have been explored for their potential application as antifungal agents. In this work, we report the evaluation of 1039 metal-containing compounds that were screened by the Community for Open Antimicrobial Drug Discovery (CO-ADD). We show that 20.9% of all metal compounds tested have antimicrobial activity against two representative Candida and Cryptococcus strains compared with only 1.1% of the >300,000 purely organic molecules tested through CO-ADD. We identified 90 metal compounds (8.7%) that show antifungal activity while not displaying any cytotoxicity against mammalian cell lines or hemolytic properties at similar concentrations. The structures of 21 metal complexes that display high antifungal activity (MIC ≤1.25 μM) are discussed and evaluated further against a broad panel of yeasts. Most of these have not been previously tested for antifungal activity. Eleven of these metal complexes were tested for toxicity in the Galleria mellonella moth larva model, revealing that only one compound showed signs of toxicity at the highest injected concentration. Lastly, we demonstrated that the organo-Pt(II) cyclooctadiene complex Pt1 significantly reduces fungal load in an in vivo G. mellonella infection model. These findings showcase that the structural and chemical diversity of metal-based compounds can be an invaluable tool in the development of new drugs against infectious diseases.

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Section: Introductionmentioning

confidence: 99%

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Frei

Elliott

Kan

et al. 2022

JACS Au

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show abstract

“…Over the last years a small number of reports have been published on several different antifungal metal complexes. 28,30,[34][35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50][51] Figure 1 presents an overview of selected metal compounds with measured antifungal activity. Gasser and coworkers recently published an expansive review of the metalbased antifungals research field.…”

Section: Introductionmentioning

confidence: 99%

Metal Complexes as Antifungals? – From a Crowd-Sourced Compound Library to First In Vivo Experiments

Frei

Elliott

Kan

et al. 2022

Preprint

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There are currently fewer than ten antifungal drugs in clinical development, but new fungal strains, which are resistant to most current antifungals are spreading rapidly across the world. To prevent a second resistance crisis, new classes of antifungal drugs are urgently needed. Metal complexes have proven to be promising candidates for novel antibiotics, but so far, few compounds have been explored for their potential application as antifungal agents. In this work we report the evaluation of 1039 metal-containing compounds that were screened by the Community for Open Antimicrobial Drug Discovery (CO-ADD). We show that 20.9% of all metal compounds tested have antimicrobial activity against two representative Candida and Cryptococcus strains, compared with only 1.1% of the >300,000 purely organic molecules tested through CO-ADD. We identified 90 metal compounds (8.7%) that show antifungal activity while not displaying any cytotoxicity against mammalian cell lines or haemolytic properties at similar concentrations. The structures of 21 metal complexes which display high antifungal activity (MIC ≤ 1.25 µM) are discussed and evaluated further against a broad panel of yeasts. Most of these have not been evaluated for antifungal activity. Eleven of these metal complexes were tested for toxicity in the Galleria mellonella moth larvae model, revealing that only one compound showed signs of toxicity at the highest injected concentration. Lastly, we demonstrated that the organo-Pt(II) cyclooctadiene complex Pt1 significantly reduces fungal load in an in vivo G. mellonella infection model. These findings showcase that the structural and chemical diversity of metal-based compounds can be an invaluable tool in the development of new drugs against infectious diseases.

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Organotin (IV) Complexes as Catalyst for Biodiesel Formation: Synthesis, Structural Elucidation and Computational Studies

Zubair

Sirajuddin

Haider

et al. 2019

Applied Organom Chemis

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Here we have presented the synthesis of three novel triorganotin (IV) complexes: trimethylstannyl 4‐(3‐chloro‐2‐methylphenylamino)‐4‐oxobut‐2‐enoate (1); tributylstannyl 4‐(3‐chloro‐2‐methylphenylamino)‐4‐oxobut‐2‐enoate (2) and triphenylstannyl 4‐(3‐chloro‐2‐methylphenylamino)‐4‐oxobut‐2‐enoate (3). The ligand and its three complexes were spectroscopically characterized by NMR (1H and 13C) in solution and by FT‐IR in solid state. Complexes 1 and 2 were further characterized by single crystal X‐ray diffraction analysis. The X‐ray crystallographic data reveal that complexes 1 and 2 both are structurally trialkytin(IV) analogs with distorted trigonal bipyramidal geometry. The geometry around tin atom is constituted by three alkyl groups (methyl in complex 1 and butyl in complex 2) occupying the equatorial positions and two oxygen atoms of 4‐(3‐chloro‐2‐methylphenylamino)‐4‐oxobut‐2‐enoic acid ligand occupying the axial positions. The computational study was performed applying LANL2DZ (Los Alamos National Laboratory 2 Double‐Zeta) functional with B3LYP (Lee, Yang and Parr) level of theory to obtain the optimized geometry, spectroscopic analysis, frontier molecular orbitals as well as global and local reactivity. A good correlation was found between the experimental and computational results. The homogeneous catalytic performance of synthesized compounds was evaluated for the transesterification of corn oil with methanol into biodiesel. The obtained corn oil biodiesel (COB) was confirmed by FT‐IR, 1H NMR and GC–MS. The catalytic results revealed that the complexes were active at optimized conditions and therefore can be potential candidates for the development of new catalytic system for biodiesel production.

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Syntheses, characterization and antifungal activity of novel dimethylbis(N-R-sulfonyldithiocarbimato)stannate(IV) complexes

Cited by 11 publications

References 26 publications

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Metal Complexes as Antifungals? From a Crowd-Sourced Compound Library to the First In Vivo Experiments

Metal Complexes as Antifungals? – From a Crowd-Sourced Compound Library to First In Vivo Experiments

Organotin (IV) Complexes as Catalyst for Biodiesel Formation: Synthesis, Structural Elucidation and Computational Studies

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