Indole-nitroimidazole conjugates as efficient manipulators to decrease the genes expression of methicillin-resistant Staphylococcus aureus

Li, Zhenzhen; Tangadanchu, Vijai Kumar Reddy; Battini, Narsaiah; Bheemanaboina, Rammohan R. Yadav; Zang, Zhong‐Lin; Zhang, Shaolin

doi:10.1016/j.ejmech.2019.06.093

Cited by 64 publications

(29 citation statements)

References 52 publications

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“…Metronidazole (MET) is an azomycin-derived nitroimidazole discovered in 1962, which is commonly used to treat skin, bones and tissues infections. It can act as antimicrobial [1], antiprotozoal [2], antiviral [3], antileishmanial [4], antigiardial [5], antioxidant [6], anti-inflammatory [7], antiplasmodial and antimycobacterial [8]. Regularly, besides the mentioned applications, MET is highly indicated for the treatment of infections caused by drug-resistant bacteria (anaerobic Grampositive and Gram-negative bacteria), tuberculosis, protozoan infections (trichomoniasis, amoebiasis, bacterial vaginosis, giardiasis, non-gonococcal urethritis) and visceral leishmaniasis [9].…”

Section: Introductionmentioning

confidence: 99%

Silver nanoparticles effect on drug release of metronidazole in natural rubber latex dressing

et al. 2021

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Natural rubber latex (NRL) from Hevea brasiliensis has shown great potential for dermal applications due to its angiogenesis capacity and biocompatibility. Metronidazole (MET) is a synthetic antibiotic used to treat various infections. However, this drug reports dangerous effects when high concentrations are administered. In this study, we used silver nanoparticles (AgNPs) in order to minimize these toxicological effects. For this, the membranes were characterized by physicochemical, molecular modeling, in vitro release and hemocompatibility assays. In the release assays, 14.25% of the MET and 27.28% of the AgNP + MET complex were released simultaneously, indicating that these nanoparticles work as drug carriers. Molecular modeling simulation helped to explain the in vitro release results, showing that AgNPs can interact more efficiently with MET molecules. Moreover, similarities in reactivity between NRL and MET suggested that some drug molecules may remain in the matrix during the release process. The membranes did not present significant hemolytic activity after 24 h of incubation. These results demonstrated that the NRL + AgNP + MET membrane can be used as a dressing in the treatment of infectious processes.

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Section: Introductionmentioning

confidence: 99%

Silver nanoparticles effect on drug release of metronidazole in natural rubber latex dressing

et al. 2021

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“…It was also discovered that (E)-3-(2-methyl-5-nitro-1H-imidazol-1-yl)-4-{1-[2-oxo-2-(piperidin-1-yl)ethyl]-1H-indol-3-yl}but-3-en-2-one (142b) possessed a satisfactory inhibitory activity on MRSA (MIC = 2 µM) and could effectively prevent the development of bacterial resistance, could intercalate into DNA, and also permeate MRSA membrane. It is worth noting that this hybrid also exhibited low cytotoxicity towards normal lung epithelial cell line BEAS-2B [80].…”

Section: It Was Then Found That 2-mentioning

confidence: 97%

“…Still in 2013, Zhu and coworkers reported that the Schiff's base derivative 78 bearing a 5-nitroimidazole moiety exhibited effective inhibitory activity towards E. coli ATCC 35218 (MIC = 7.1 μM) that was similar to that of both standards used, kanamycin B and penicillin G (6.5 and 9.4 µM, respectively) [51]. (E)-N'-[1-(4-Bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylidene] isonicotinohydrazide (78) was synthesised via a two-step protocol in which the first step involved the preparation of the key intermediate, 1-(4-bromophenyl)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethan-1-one (79) by treatment of 2-methyl-5-nitro-1H-imidazole (64) with 2-bromo-1-(4-bromophenyl)ethan-1-one (80) [52]. The developed synthetic route involved the conversion of naturally occurring 83, a compound of which many derivatives have been shown to possess interesting biological activities [53,54], to intermediate 84 as described in the literature [55].…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

“…In 2019, Zang, Zhang, Zhou, and coworkers turned their attention to the development of novel compounds possessing the ability to combat the resistance of Gram-positive pathogen MRSA [80]. Hybrids 137 and 138 were then tested for their in vitro antibacterial activities against five Gram-positive bacterial strains (MRSA, S. aureus, S. aureus ATCC 25923, S. aureus ATCC 29213, and E. faecalis) and six Gram-negative bacterial strains (E. coli, E. coli ATCC 25922, K. pneumoniae, P. aeruginosa, P. aeruginosa ATCC 27853, and A. baumannii).…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

“…In 2019, Zang, Zhang, Zhou, and coworkers turned their attention to the development of novel compounds possessing the ability to combat the resistance of Gram-positive pathogen MRSA [80]. The resistance is due to the acquisition of mecA gene, which, unlike of any PBP (penicillin binding protein) normally produced by S. aureus, encodes the protein PBP2a that has a low affinity for β-lactam antibiotics such as penicillin and methicillin [80]. In particular, the above-mentioned researchers directed their efforts towards the development of novel structural candidates of enone-bridged indole/nitroimidazole scaffolds.…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

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An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

Rossi

Ciofalo

2020

Molecules

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The rapid growth of serious infections caused by antibiotic resistant bacteria, especially the nosocomial ESKAPE pathogens, has been acknowledged by Governments and scientists and is one of the world’s major health problems. Various strategies have been and are currently investigated and developed to reduce and/or delay the bacterial resistance. One of these strategies regards the design and development of antimicrobial hybrids and conjugates. This unprecedented critical review, in which our continuing interest in the synthesis and evaluation of the bioactivity of imidazole derivatives is testified, aims to summarise and comment on the results obtained from the end of the 1900s until February 2020 in studies conducted by numerous international research groups on the synthesis and evaluation of the antibacterial properties of imidazole-based molecular hybrids and conjugates in which the pharmacophoric constituents of these compounds are directly covalently linked or connected through a linker or spacer. In this review, significant attention was paid to summarise the strategies used to overcome the antibiotic resistance of pathogens whose infections are difficult to treat with conventional antibiotics. However, it does not include literature data on the synthesis and evaluation of the bioactivity of hybrids and conjugates in which an imidazole moiety is fused with a carbo- or heterocyclic subunit.

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Novel Schiff Base‐conjugated para‐Aminobenzenesulfonamide Indole Hybrids as Potentially Muti‐targeting Blockers against Staphylococcus aureus

Zhang

Huang

et al. 2022

Asian J Org Chem

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Staphylococcus aureus (S. aureus) has developed strong resistance to a variety of clinical antibiotics, which makes the design and synthesis of novel structural molecules with outstanding antibacterial potential put on the agenda. The results of bioactivity assessment displayed that sulfonamide indole compound 4 h, which was modified with a butene group, had remarkable antibacterial activity against S. aureus (MIC=5 μM), and was superior to the reference drugs norfloxacin (MIC=13 μM) and sulfathiazole (MIC=501 μM). The propensity of evaluation of hybrid 4 h to induce drug resistance was lower than that of the reference drugs. In addition, the cytotoxicity assay revealed that compound 4 h had no obvious cytotoxicity to normal mammalian cells (RAW 264.7). Molecular docking analysis further demonstrated that the highly active molecule 4 h could interact with the active sites of DNA hexamer duplex and human carbonic anhydrase isozyme II through hydrogen bonds. Moreover, preliminary mechanistic studies indicated that hybrid 4 h prospectively acted as an blocker by disrupting the bacterial membrane of S. aureus and inserting itself into S. aureus DNA to prevent strains from replicating.

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Indole-nitroimidazole conjugates as efficient manipulators to decrease the genes expression of methicillin-resistant Staphylococcus aureus

Cited by 64 publications

References 52 publications

Silver nanoparticles effect on drug release of metronidazole in natural rubber latex dressing

Silver nanoparticles effect on drug release of metronidazole in natural rubber latex dressing

An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

Novel Schiff Base‐conjugated para‐Aminobenzenesulfonamide Indole Hybrids as Potentially Muti‐targeting Blockers against Staphylococcus aureus

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