Sulfamethoxazole derivatives complexed with metals: a new alternative against biofilms of rapidly growing mycobacteria

Siqueira, Fallon dos Santos; Rossi, Grazielle Guidolin; Machado, Alencar Kolinski; Alves, Camilla F.S.; Flores, Vanessa C.; Somavilla, Viviane Drescher; Agertt, Vanessa Albertina; Siqueira, Josiéli Demetrio; Dias, Renne de Sousa; Copetti, Priscila Marquezan; Sagrillo, Michele Rorato; Back, Davi F.; Campos, Marli Matiko Anraku de

doi:10.1080/08927014.2018.1514497

Cited by 17 publications

(4 citation statements)

References 98 publications

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“…Overall, the results obtained in our study demonstrate high MIC values for sulfamethoxazole against Gram‐negative and Gram‐positive microorganisms (3125 μg mL −1 ). Moreover, considering the dosage breakpoints listed in the standard protocols, [31] we observed a resistance profile to sulfamethoxazole presented by M. massiliense , as already reported in the studies by Siqueira et al [35] . and Flores et al [36] .…”

Section: Resultssupporting

confidence: 83%

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Azevedo-Barbosa

Vale

Rossi

et al. 2021

Chemistry & Biodiversity

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Using molecular hybridization, specific sulfonamide derivatives of eugenol were synthesized with subtle modifications in the allylic chain of the eugenol subunit (and also in the nature of the substituent group in the sulfonamide aromatic ring) which allowed us to study the influence of structural changes on the antimicrobial potential of the hybrids. Antimicrobial test results showed that most of the synthesized hybrid compounds showed good activity with better results than the parent compounds. Molecular docking studies of the hybrids with the essential bacterial enzyme DHPS showed complexes with low binding energies, suggesting that DHPS could be a possible target for the antibacterial sulfonamide‐eugenol hybrids. Furthermore, most of the final compounds presented similar docking poses to that of the crystallographic ligand sulfamethoxazole. The results obtained allow us to conclude that these are promising compounds for use as new leads in the search for new antibacterial sulfonamides.

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Section: Resultssupporting

confidence: 83%

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Azevedo-Barbosa

Vale

Rossi

et al. 2021

Chemistry & Biodiversity

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“…On the other hand, Flores and co-workers evaluated the antibiofilm activity of different antibiotics used in the treatment of mycobacterial infections (amikacin, ciprofloxacin, clarithromycin, doxycycline, imipenem and sulfamethoxazole), but none of them was able to significantly prevent biofilm formation or to promote biofilm dispersal [244]. Nevertheless, it was recently found that sulfamethoxazole when in complex with metal ions, particularly in complex with Au, showed a markedly enhanced antibiofilm activity [245]. Moreover, showing these compounds a good safety profile and antibacterial activity, they have been suggested as potential therapeutic agents [245].…”

Section: Emerging Cf Pathogensmentioning

confidence: 99%

“…Nevertheless, it was recently found that sulfamethoxazole when in complex with metal ions, particularly in complex with Au, showed a markedly enhanced antibiofilm activity [245]. Moreover, showing these compounds a good safety profile and antibacterial activity, they have been suggested as potential therapeutic agents [245].…”

Section: Emerging Cf Pathogensmentioning

confidence: 99%

Quorum Sensing as Antivirulence Target in Cystic Fibrosis Pathogens

Scoffone

Trespidi

Chiarelli

et al. 2019

IJMS

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Cystic fibrosis (CF) is an autosomal recessive genetic disorder which leads to the secretion of a viscous mucus layer on the respiratory epithelium that facilitates colonization by various bacterial pathogens. The problem of drug resistance has been reported for all the species able to colonize the lung of CF patients, so alternative treatments are urgently needed. In this context, a valid approach is to investigate new natural and synthetic molecules for their ability to counteract alternative pathways, such as virulence regulating quorum sensing (QS). In this review we describe the pathogens most commonly associated with CF lung infections: Staphylococcus aureus, Pseudomonas aeruginosa, species of the Burkholderia cepacia complex and the emerging pathogens Stenotrophomonas maltophilia, Haemophilus influenzae and non-tuberculous Mycobacteria. For each bacterium, the QS system(s) and the molecules targeting the different components of this pathway are described. The amount of investigations published in the last five years clearly indicate the interest and the expectations on antivirulence therapy as an alternative to classical antibiotics.

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“…Few reports of antibiofilm activity of cadmium complexes are available in the literature. Likewise, two tetranuclear Cd (II) complexes with salen‐type Schiff base ligands showed antibiofilm activity against Enterococcus gallinarum MTCC7049 and Proteus vulgaris MTCC744, 15 whereas the [Cd (sulfamethoxazolate) 2 ] complex showed greater biofilm inhibition (and destruction of already formed biofilm) than the free antibiotic against Mycobacterium fortuitum and Mycobacterium abscessus 28 . To our knowledge, the present work is the first report of antibiofilm activity of cadmium (II) complexes with N‐ and O‐containing ligands against the P .…”

Section: Introductionmentioning

confidence: 99%

Computational studies, antimicrobial activity, inhibition of biofilm production, and safety profile of the cadmium complex of 1,10‐phenanthroline and cyanoguanidine

Falkievich

Medina

Alegre

et al. 2022

Applied Organom Chemis

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We have previously determined the crystal structure of the metal complex [Cd (1,10-phenanthroline) 2 (SO 4 )H 2 O]cyanoguanidine•5H 2 O that was characterized by spectroscopic measurements. The antibacterial activity was also determined by the agar diffusion test (zones of inhibition). In the present work, calculations based on density functional theory were performed to determine the contributions of the two different tautomers of cyanoguanidine to the vibrational IR and Raman experimental spectra. Moreover, the antimicrobial (antibacterial and antifungal) activity of the complex and cadmium ion was assessed and the minimum inhibitory concentration (MIC) was determined.The complexation increased the antimicrobial activity against Pseudomonas aeruginosaATCC 27853 and inhibited the biofilm production of this pathogen.Antimicrobial studies were coupled with the evaluation of safety, using the Artemia salinaand Ames test. At the concentrations tested, the cadmium complex behaved as a non-mutagenic and non-toxic compound. Therefore, the interaction of cadmium (II) with N and O-containing ligands may provide a promising strategy for the development of novel and safe drugs with antimicrobial activity.

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Sulfamethoxazole derivatives complexed with metals: a new alternative against biofilms of rapidly growing mycobacteria

Cited by 17 publications

References 98 publications

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Design, Synthesis, Antimicrobial Evaluation and in Silico Studies of Eugenol‐Sulfonamide Hybrids

Quorum Sensing as Antivirulence Target in Cystic Fibrosis Pathogens

Computational studies, antimicrobial activity, inhibition of biofilm production, and safety profile of the cadmium complex of 1,10‐phenanthroline and cyanoguanidine

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