Discovery of natural berberine-derived nitroimidazoles as potentially multi-targeting agents against drug-resistant Escherichia coli

Zhang, Guobiao; Maddili, Swetha Kameswari; Tangadanchu, Vijai Kumar Reddy; Goodla, Lavanya; Gao, Wei‐Wei; Cai, Gui‐Xin

doi:10.1007/s11426-017-9169-4

Cited by 63 publications

(36 citation statements)

References 59 publications

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“…In 2018, Cai, Zhou, and coworkers synthesised berberine/nitroimidazole hybrids 125 via the reaction sequence outlined in Scheme 23, in which berberine (70) was the starting material [69]. Berberrubine (74), which was obtained in 90% yield by selective demethylation of 70, was reduced with NaBH4 in MeOH generating compound 126 in 57% yield.…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

“…In 2018, Cai, Zhou, and coworkers synthesised berberine/nitroimidazole hybrids 125 via the reaction sequence outlined in Scheme 23, in which berberine (70) was the starting material [69]. Berberrubine (74) pneumoniae, E. coli, E. coli ATCC 25922, P. aeruginosa, P. aeruginosa ATCC 27853, and A. baumannii and found that, among these compounds, tetrahydroberberine-9-(2-fluorobenzyl)-12-[2-(2-methyl-5-nitroimidazolyl)acrylonitrile (125p) (R 1 = 2-FC6H4, n = 1) a berberine/nitroimidazole hybrid with an improved aqueous solubility (4.54 ± 0.08 µg/mL), not only exhibited strong antibacterial activity against drug resistant E. coli with an MIC value of 3 µM and was 33 times more potent than norfloxacin, but also displayed low toxicity towards RAW 264.7 mouse cancer cells.…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

“…They also reported that resistance in E. coli, Klebsiella spp., and Enterobacter spp. is mainly related to the production of extended-spectrum β-lactamase, but other resistance mechanisms are also possible [69].…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

“…Kumar and coworkers [70], in continuation of their studies on the synthesis of new anti-tubercular scaffolds [71,72], synthesised nitroimidazole/7-chloroquinoline conjugates 131a-d pneumoniae, E. coli, E. coli ATCC 25922, P. aeruginosa, P. aeruginosa ATCC 27853, and A. baumannii and found that, among these compounds, tetrahydroberberine-9-(2-fluorobenzyl)-12-[2-(2-methyl-5-nitroimidazolyl)acrylonitrile (125p) (R 1 = 2-FC 6 H 4 , n = 1) a berberine/nitroimidazole hybrid with an improved aqueous solubility (4.54 ± 0.08 µg/mL), not only exhibited strong antibacterial activity against drug resistant E. coli with an MIC value of 3 µM and was 33 times more potent than norfloxacin, but also displayed low toxicity towards RAW 264.7 mouse cancer cells. Cai, Zhou, and coworkers also investigated the antibacterial mechanism and found that compound 125p might target E. coli DNA polymerase II through the formation of hydrogen bonds, effectively permeability-resistant E. coli cell membrane, and intercalate into DNA isolated from resistant E. coli to form 125p-DNA complex, thus blocking DNA replication [69]. They also reported that resistance in E. coli, Klebsiella spp., and Enterobacter spp.…”

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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“…In 2018, Cai, Zhou, and coworkers synthesised berberine/nitroimidazole hybrids 125 via the reaction sequence outlined in Scheme 23, in which berberine (70) was the starting material [69]. Berberrubine (74), which was obtained in 90% yield by selective demethylation of 70, was reduced with NaBH4 in MeOH generating compound 126 in 57% yield.…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

“…In 2018, Cai, Zhou, and coworkers synthesised berberine/nitroimidazole hybrids 125 via the reaction sequence outlined in Scheme 23, in which berberine (70) was the starting material [69]. Berberrubine (74) pneumoniae, E. coli, E. coli ATCC 25922, P. aeruginosa, P. aeruginosa ATCC 27853, and A. baumannii and found that, among these compounds, tetrahydroberberine-9-(2-fluorobenzyl)-12-[2-(2-methyl-5-nitroimidazolyl)acrylonitrile (125p) (R 1 = 2-FC6H4, n = 1) a berberine/nitroimidazole hybrid with an improved aqueous solubility (4.54 ± 0.08 µg/mL), not only exhibited strong antibacterial activity against drug resistant E. coli with an MIC value of 3 µM and was 33 times more potent than norfloxacin, but also displayed low toxicity towards RAW 264.7 mouse cancer cells.…”

Section: It Was Then Found That 2-mentioning

confidence: 99%

Section: It Was Then Found That 2-mentioning

confidence: 99%

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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“…6 | ANTI -BAC TERIAL PROPERT YThe study screened the five protoberberine alkaloids by microcalorimetry and confirmed berberine and coptisine were more appropriate candidates as new anti-infective drug 69. Berberine is now already a widely used anti-bacterial applied in the fight against diseases such as bacteria diarrhoea and fungi infection 6,70,71. Similarly, coptisine (50 μmol/L, 0-120s) was revealed to reduce S.aureus adhesion and inhibit PfDHODH, an anti-malarial chemotherapy target 72.…”

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confidence: 93%

Coptisine fromCoptis chinensisexerts diverse beneficial properties: A concise review

Luo

Deng

et al. 2019

J Cellular Molecular Medi

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Coptisine is a natural small‐molecular compound extracted from Coptis chinensis (CC) with a history of using for thousands of years. This work aimed at summarizing coptisine's activity and providing advice for its clinical use. We analysed the online papers in the database of SciFinder, Web of Science, PubMed, Google scholar and CNKI by setting keywords as ‘coptisine’ in combination of ‘each pivotal pathway target’. Based on the existing literatures, we find (a) coptisine exerted potential to be an anti‐cancer, anti‐inflammatory, CAD ameliorating or anti‐bacterial drug through regulating the signalling transduction of pathways such as NF‐κB, MAPK, PI3K/Akt, NLRP3 inflammasome, RANKL/RANK and Beclin 1/Sirt1. However, we also (b) observe that the plasma concentration of coptisine demonstrates obvious non‐liner relationship with dosage, and even the highest dosage used in animal study actually cannot reach the minimum concentration level used in cell experiments owing to the poor absorption and low availability of coptisine. We conclude (a) further investigations can focus on coptisine's effect on caspase‐1‐involved inflammasome assembling and pyroptosis activation, as well as autophagy. (b) Under circumstance of promoting coptisine availability by pursuing nano‐ or microrods strategies or applying salt‐forming process to coptisine, can it be introduced to clinical trial.

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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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Discovery of natural berberine-derived nitroimidazoles as potentially multi-targeting agents against drug-resistant Escherichia coli

Cited by 63 publications

References 59 publications

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

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

Coptisine fromCoptis chinensisexerts diverse beneficial properties: A concise review

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

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