Quinoline and quinolone dimers and their biological activities: An overview

Chu, Xue-mei; Wang, Cong; Liu, Wen; Liang, Lili; Gong, Kaikai; Zhao, Chengying; Sun, Kunlai

doi:10.1016/j.ejmech.2018.10.035

Cited by 179 publications

(57 citation statements)

References 140 publications

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“…The quinoline moiety is a well-known entity and is a ubiquitous alkaloid subunit of many natural products. Quinoline is an important pharmacophore moiety as it has been described to possess various biological activities, which include antimalarial, antibiotic, antitubercular, antiproliferative, antiprotozoal, antihypertensive and anti-HIV properties [82][83][84]. Currently various clinical drugs available in the market contain this moiety ( Figure 33).…”

Section: Quinolinesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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The analogs of nitrogen-based heterocycles occupy an exclusive position as a valuable source of therapeutic agents in medicinal chemistry. More than 75% of drugs approved by the FDA and currently available in the market are nitrogen-containing heterocyclic moieties. In the forthcoming decade, a much greater share of new nitrogen-based pharmaceuticals is anticipated. Many new nitrogen-based heterocycles have been designed. The number of novel N-heterocyclic moieties with significant physiological properties and promising applications in medicinal chemistry is ever-growing. In this review, we consolidate the recent advances on novel nitrogen-containing heterocycles and their distinct biological activities, reported over the past one year (2019 to early 2020). This review highlights the trends in the use of nitrogen-based moieties in drug design and the development of different potent and competent candidates against various diseases.

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Section: Quinolinesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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Section: Discussionmentioning

confidence: 99%

“…Fluoroquinolones (FQs) induce bacterial cell death by trapping type II topoisomerases and DNA as a ternary complex, which results in DNA breakage . As a consequence, DNA resealing is prevented and chromosome fragmentation occurs, which disrupts the process of DNA replication . The exclusive target site for FQs in H pylori is DNA gyrase, a type II topoisomerase which introduces negative DNA supercoils, in an ATP‐dependent manner .…”

Section: Discussionmentioning

confidence: 99%

New insights into resistance of Helicobacter pylori against third‐ and fourth‐generation fluoroquinolones: A molecular docking study of prevalent GyrA mutations

et al. 2019

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Background: Fluoroquinolones hinder bacterial DNA replication by inhibiting DNA gyrase. However, mutations, in the QRDR segment of its A subunit (GyrA), cause antibiotic resistance. Here, the interactions of levofloxacin (LVX), gemifloxacin (GXN), and moxifloxacin (MXN) with Helicobacter pylori GyrA, in LVX-resistant vs -sensitive strains, were studied. Methods: Levoflixacin-sensitive (n = 4) and -resistant (n = 9) H pylori strains, randomly selected from another antibiotic susceptibility study, underwent PCR amplification of gyrA gene, spanning the QRDR segment. The amplified gene fragments were sequenced and aligned. The homology model of H pylori GyrA was built based on that of Escherichia coli, and energy minimization was done. The interaction patterns of LVX, GXN, and MXN with GyrA were analyzed via molecular docking studies. Results: Sequence alignment of the 13 studied strains, created 5 categories of strains: (A) wild type-like (H pylori ATCC26695), (B) N87K-only, (C) D91N-only, (D) N87K + V94L, and (E) D91N + A97V mutations. The minimum inhibitory concentrations (MIC) for LVX-sensitive (category A) and -resistant (categories B-E) strains were <1 mg/L and ≥32 mg/L, respectively. The binding mode of GyrA in category A withLVX identified G35/N87/Y90/D91/V94/G114/S115/I116/D117/G118/D119, as key residues, some residing outside the QRDR segment. Category B strains lost only one interaction (G35), which led to elevated binding free energy (∆G) and full LVX resistance. Categories C-E lost more contacts, with higher ∆G and again full LVX resistance. GXN bound to GyrA of categories A and B via a different set of key residues, while MXN retained the lost contact (G35) in LVX-resistant, category B strains. Conclusion:Using molecular docking tools, we identified the key residues responsible for interaction of GyrA with LVX, GXN, and MXN. In the presence of N87K-only mutation, the loss of one of these contacts (ie, G35) led to full LVX resistance. Yet, GXN and MXN overcame this mutation, by retaining all key contacts with GyrA.

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“…Promising candidates for development of new drug are dimeric molecules since they exhibit some unique properties in comparison to corresponding monomer, such as enhanced biological activity. In the last three decades, numerous quinoline and quinolone dimers were assessed for their biological activities, including antimicrobial, and quite recently very detailed review article has been published on the subject (Chu et al 2019); hence, quinoline/quinolone dimeric molecules are not reviewed here.…”

Section: Antibacterial Activitymentioning

confidence: 99%

Quinolines and Quinolones as Antibacterial, Antifungal, Anti-virulence, Antiviral and Anti-parasitic Agents

Šenerović

Opsenica

Morić

et al. 2019

Advances in Experimental Medicine and Biology

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Infective diseases have become health threat of a global proportion due to appearance and spread of microorganisms resistant to majority of therapeutics currently used for their treatment. Therefore, there is a constant need for development of new antimicrobial agents, as well as novel therapeutic strategies. Quinolines and quinolones, isolated from plants, animals, and microorganisms, have demonstrated numerous biological activities such as antimicrobial, insecticidal, antiinflammatory, antiplatelet, and antitumor. For more than two centuries quinoline/quinolone moiety has been used as a scaffold for drug development and even today it represents an inexhaustible inspiration for design and development of novel semi-synthetic or synthetic agents exhibiting broad spectrum of bioactivities. The structural diversity of synthetized compounds provides high and selective activity attained through different mechanisms of action, as well as low toxicity on human cells. This review describes quinoline and quinolone derivatives with antibacterial, antifungal, anti-virulent, antiviral, and anti-parasitic activities with the focus on the last 10 years literature.

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Quinoline and quinolone dimers and their biological activities: An overview

Cited by 179 publications

References 140 publications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

New insights into resistance of Helicobacter pylori against third‐ and fourth‐generation fluoroquinolones: A molecular docking study of prevalent GyrA mutations

Quinolines and Quinolones as Antibacterial, Antifungal, Anti-virulence, Antiviral and Anti-parasitic Agents

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