Recent advancements in the medicinal chemistry of bacterial type II topoisomerase inhibitors

Jaswal, Shalini; Nehra, Bhupender; Kumar, Shiva; Monga, Vikramdeep

doi:10.1016/j.bioorg.2020.104266

Cited by 17 publications

(8 citation statements)

References 111 publications

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“…Topoisomerases are major enzymes that play an important role in DNA replication. [103,104] Several anthraquinones actively target these enzymes; for instance, 2,4-diidoemodin 81 d showed much lower MIC against MRSA, vancomycinresistant Enterococcus faecium compared to cefoxitin (Figure 5) as it selectively inhibits bacterial DNA gyrase and topoisomerase I without affecting human topoisomerase. [105] Further investigations showed that 2,4-diiodoemodin also disrupts the cell membrane, and increased the permeability of potassium ions leading to increased extracellular potassium ion concentration.…”

Section: Interfering With Dna Replicationmentioning

confidence: 99%

“…Antimicrobials commonly target fundamental cellular activities including DNA replication, cell wall synthesis, major metabolic pathways and protein synthesis to effectively target microbial species. Topoisomerases are major enzymes that play an important role in DNA replication [103,104] . Several anthraquinones actively target these enzymes; for instance, 2,4‐diidoemodin 81 d showed much lower MIC against MRSA, vancomycin‐resistant Enterococcus faecium compared to cefoxitin (Figure 5) as it selectively inhibits bacterial DNA gyrase and topoisomerase I without affecting human topoisomerase [105]…”

Section: Mechanisms Underlying Antibacterial Activitymentioning

confidence: 99%

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Exploring Anthraquinones as Antibacterial and Antifungal agents

et al. 2023

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Anthraquinones having an anthracene core structure with two carbonyl groups are essential compounds in therapeutic applications. One of the growing concerns within the medical community is antimicrobial resistance. Multiple drug-resistant microbes can worsen a disease that can be easily treated with normal drugs. Microbes also produce biofilms that further enhance their resistance to antimicrobials, rendering biofilm-associated infections challenging to eradicate. This review provides an update on the antibacterial and antifungal activities of natural and synthetic anthraquinone derivatives. The mechanism of antibacterial and antifungal action of anthraquinones are summarised, which will help in designing new therapeutically effective anthraquinone compounds.

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Section: Interfering With Dna Replicationmentioning

confidence: 99%

Section: Mechanisms Underlying Antibacterial Activitymentioning

confidence: 99%

Exploring Anthraquinones as Antibacterial and Antifungal agents

et al. 2023

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“…DNA topoisomerases are ubiquitous enzymes that carry out DNA‐strand passing activities, which are crucial to the physiological processes that regulate the genome. These inhibitors bind to the DNA strands, separate and reconnect DNA strands, and alter the DNA structure (Jaswal et al, 2020). DNA topoisomerases as enzymes are involved in numerous biological activities that involve DNA unlinking.…”

Section: Anticancer Profile Of Quinoline‐based Derivativesmentioning

confidence: 99%

Molecular target interactions of quinoline derivatives as anticancer agents: A review

et al. 2022

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One of the leading causes of death worldwide is cancer, which poses substantial risks to both society and an individual's life. Cancer therapy is still challenging, despite developments in the field and continued research into cancer prevention. The search for novel anticancer active agents with a broader cytotoxicity range is therefore continuously ongoing. The benzene ring gets fused to a pyridine ring at two carbon atoms close to one another to form the double ring structure of the heterocyclic aromatic nitrogen molecule known as quinoline (1‐azanaphthalene). Quinoline derivatives contain a wide range of pharmacological activities, including antitubercular, antifungal, antibacterial, and antimalarial properties. Quinoline derivatives have also been shown to have anticancer properties. There are many quinoline derivatives widely available as anticancer drugs that act via a variety of mechanisms on various molecular targets, such as inhibition of topoisomerase, inhibition of tyrosine kinases, inhibition of heat shock protein 90 (Hsp90), inhibition of histone deacetylases (HDACs), inhibition of cell cycle arrest and apoptosis, and inhibition of tubulin polymerization.

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“…It has been discovered that the functional group found in the quinolone molecule affects its ability to inhibit microbial growth. The presence of the fluoro group at the C‐6 position and the C‐4 carbonyl group on quinolone resulted in superior antibacterial and antifungal properties (Jaswal et al, 2020). Incorporating a fluoro group at the C‐6 position significantly enhances the antibacterial effect of the compound by making it more lipophilic and inhibiting DNA gyrase (Joshi et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

Arylidene and amino spacer‐linked rhodanine‐quinoline hybrids as upgraded antimicrobial agents

Khalifa,

Upadhyay,

Patel

2023

Chem Biol Drug Des

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Antibiotic resistance associated with various microorganisms such as Gram‐positive, Gram‐negative, fungal strains, and multidrug‐resistant tuberculosis increases the risk of healthcare survival. Preliminary therapeutics becoming ineffective that might lead to noteworthy mortality presents a crucial challenge for the scientific community. Hence, there is an urgent need to develop hybrid compounds as antimicrobial agents by combining two or more bioactive heterocyclic moieties into a single molecular framework with fewer side effects and a unique mode of action. This review highlights the recent advances (2013–2023) in the pharmacology of rhodanine‐linked quinoline hybrids as more effective antimicrobial agents. In the drug development process, linker hybrids acquire the top position due to their excellent π‐stacking and Van der Waals interaction with the DNA active sites of pathogens. A molecular hybridization strategy has been optimized, indicating that combining these two bioactive moieties with an arylidene and an amino spacer linker increases the antimicrobial potential and reduces drug resistance. Moreover, the structure–activity relationship study is discussed to express the role of various functional groups in improving and decrementing antimicrobial activities for rational drug design. Also, a linker approach may accelerate the development of dynamic antimicrobial agents through molecular hybridization.

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Recent advancements in the medicinal chemistry of bacterial type II topoisomerase inhibitors

Cited by 17 publications

References 111 publications

Exploring Anthraquinones as Antibacterial and Antifungal agents

Exploring Anthraquinones as Antibacterial and Antifungal agents

Molecular target interactions of quinoline derivatives as anticancer agents: A review

Arylidene and amino spacer‐linked rhodanine‐quinoline hybrids as upgraded antimicrobial agents

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