Optimization of activity localization of quinoline derivatives: Design, synthesis, and dual evaluation of biological activity for potential antitumor and antibacterial agents

Jin, Guofan; Li, Zhenwang; Xiao, Fuyan; Qi, Xueyong; Sun, Xuerong

doi:10.1016/j.bioorg.2020.103837

Cited by 26 publications

(4 citation statements)

References 50 publications

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“…Quinolines are one of the most important nitrogenous heterocyclic compounds that have been extensively examined due to their widespread pharmacology appliances, such as anti-malarial, antitumor, anti-parasitic, antibacterial, anti-asthma, antidiabetic, anti-inflammatory, antiplatelet, and antihypertensive activities [ 95 , 96 , 97 , 98 , 99 , 100 , 101 , 102 ]. Streptonigrin (isolated from Streptomyces flocculus ) and lavendamycin have already been known as antimicrobial and antitumor compounds with quinoline skeleton ( Scheme 9 ); they create efficient interactions with targets to act as a cancer chemotherapy agent and as Hsp90 inhibitors [ 103 , 104 , 105 ].…”

Section: Hsp90 Inhibitorsmentioning

confidence: 99%

Heterocyclic Compounds as Hsp90 Inhibitors: A Perspective on Anticancer Applications

et al. 2022

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Heat shock proteins (Hsps) have garnered special attention in cancer therapy as molecular chaperones with regulatory/mediatory effects on folding, maintenance/stability, maturation, and conformation of proteins as well as their effects on prevention of protein aggregation. Hsp90 ensures the stability of various client proteins needed for the growth of cells or the survival of tumor cells; therefore, they are overexpressed in tumor cells and play key roles in carcinogenesis. Accordingly, Hsp90 inhibitors are recognized as attractive therapeutic agents for investigations pertaining to tumor suppression. Natural Hsp90 inhibitors comprising geldanamycin (GM), reclaimed analogs of GM including 17-AAG and DMAG, and radicicol, a natural macrocyclic antifungal, are among the first potent Hsp90 inhibitors. Herein, recently synthesized heterocyclic compounds recognized as potent Hsp90 inhibitors are reviewed along with the anticancer effects of heterocyclic compounds, comprising purine, pyrazole, triazine, quinolines, coumarin, and isoxazoles molecules.

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Section: Hsp90 Inhibitorsmentioning

confidence: 99%

Heterocyclic Compounds as Hsp90 Inhibitors: A Perspective on Anticancer Applications

et al. 2022

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“…[9] Jin et al prepared a series of quinolinium iodide derivatives with bacteriostatic activity in 2020. [10] In conclusion, quinoline derivatives have broad application prospects in medicine, food, and other fields.…”

Section: Introductionmentioning

confidence: 98%

Preparation of Novel Chitosan Oligosaccharide Quaternary Ammonium Derivatives Bearing Quinoline with Antioxidative and Antibacterial Activities

et al. 2023

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In this study, five new chitosan oligosaccharide quaternary ammonium derivatives bearing quinoline are synthesized by reaction between 6‐O‐chloroacetyl‐2‐N, N, N‐trimethyl quaternary ammonium salt chitosan oligosaccharide (CTCOS, compound 1) and quinoline derivatives. The derivatives are characterized by analytical techniques including Fourier Transform Infrared (FTIR), 1H Nuclear Magnetic Resonance (1H NMR) spectroscopy, and elemental analysis. The obtained results confirm that quinoline groups are successfully introduced into the CTCOS molecule. Meanwhile, the antioxidant activities of the prepared chitosan oligosaccharide derivatives are evaluated in vitro. The experimental results show that the derivatives have excellent free radical scavenging ability. The free radical scavenging abilities are all over 75% at the concentration of 1.6 mg mL−1. Moreover, antibacterial tests show that derivative 2e has the best antibacterial activities. Its minimum inhibitory concentration (MIC) value and minimum bactericidal concentration (MBC) value against Staphylococcus aureus and Escherichia coli are 0.0625 and 0.03125 mg mL−1, respectively. In addition, the cytotoxicity of chitosan oligosaccharide and its derivatives is examined by MTT colorimetric assay in RAW 264.7 macrophages, observing that all derivatives are non‐cytotoxic. Consequently, the findings indicate that the enhanced antioxidant activity, antibacterial activity, and biocompatibility of these chitosan oligosaccharide derivatives can enlarge the scope of the application of chitosan oligosaccharides, particularly as antioxidant and antibacterial agents in food packaging, pharmaceutical, cosmetics industries, and other fields.

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“…Bazin et al [51] reported the diethyl ((N-(4-bromophenyl) sulfamoyl) (2-chloro-8-methylquinolin-3-yl) methyl) phosphonate A to have a very potent activity against E. coli, with an MIC of 0.125 µg/mL. Moreover, the quinoline benzodioxole derivative B showed excellent antibacterial activity, with an MIC of 3.125 µg/mL against E. coli and S. aureus strains [52]. The quinoline-3-carbonitrile derivative C synthesized by Khan et al [53] exhibited antibacterial potential against Gram-negative bacteria with the highest activity towards E. coli, with an MIC of 4 µg/mL.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, and Antibiofilm Activities of Some Novel 7-Methoxyquinoline Derivatives Bearing Sulfonamide Moiety against Urinary Tract Infection-Causing Pathogenic Microbes

Ghorab

Soliman

El-Sayyad

et al. 2023

IJMS

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A new series of 4-((7-methoxyquinolin-4-yl) amino)-N-(substituted) benzenesulfonamide 3(a–s) was synthesized via the reaction of 4-chloro-7-methoxyquinoline 1 with various sulfa drugs. The structural elucidation was verified based on spectroscopic data analysis. All the target compounds were screened for their antimicrobial activity against Gram-positive bacteria, Gram-negative bacteria, and unicellular fungi. The results revealed that compound 3l has the highest effect on most tested bacterial and unicellular fungal strains. The highest effect of compound 3l was observed against E. coli and C. albicans with MIC = 7.812 and 31.125 µg/mL, respectively. Compounds 3c and 3d showed broad-spectrum antimicrobial activity, but the activity was lower than that of 3l. The antibiofilm activity of compound 3l was measured against different pathogenic microbes isolated from the urinary tract. Compound 3l could achieve biofilm extension at its adhesion strength. After adding 10.0 µg/mL of compound 3l, the highest percentage was 94.60% for E. coli, 91.74% for P. aeruginosa, and 98.03% for C. neoformans. Moreover, in the protein leakage assay, the quantity of cellular protein discharged from E. coli was 180.25 µg/mL after treatment with 1.0 mg/mL of compound 3l, which explains the creation of holes in the cell membrane of E. coli and proves compound 3l’s antibacterial and antibiofilm properties. Additionally, in silico ADME prediction analyses of compounds 3c, 3d, and 3l revealed promising results, indicating the presence of drug-like properties.

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Optimization of activity localization of quinoline derivatives: Design, synthesis, and dual evaluation of biological activity for potential antitumor and antibacterial agents

Cited by 26 publications

References 50 publications

Heterocyclic Compounds as Hsp90 Inhibitors: A Perspective on Anticancer Applications

Heterocyclic Compounds as Hsp90 Inhibitors: A Perspective on Anticancer Applications

Preparation of Novel Chitosan Oligosaccharide Quaternary Ammonium Derivatives Bearing Quinoline with Antioxidative and Antibacterial Activities

Synthesis, Antimicrobial, and Antibiofilm Activities of Some Novel 7-Methoxyquinoline Derivatives Bearing Sulfonamide Moiety against Urinary Tract Infection-Causing Pathogenic Microbes

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