Development of 8-benzyloxy-substituted quinoline ethers and evaluation of their antimicrobial activities

Chung, Po Yee; Gambari, Roberto; Chen, Yi Xin; Cheng, Chor Hing; Bian, Zhaoxiang; Chan, Albert S. C.; Tang, Johnny; Leung, Polly H.M.; Chui, Chung Hin; Lam, Kim Hung

doi:10.1007/s00044-014-1217-4

Cited by 11 publications

(11 citation statements)

References 40 publications

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“…For the tested samples, 1% DMSO (as negative control) and 6 µg terbinafine (as positive control) were placed in the holes of agar. The plates were subsequently incubated at 35˚C for 48 h and the inhibition zones (mm, in terms of diameter) of fungi on the agar plates were recorded (23,25,26).…”

Section: Determination Of Mic and Minimum Fungicidal Concentration (Mmentioning

confidence: 99%

Sensitization of Candida albicans to terbinafine by berberine and berberrubine

et al. 2016

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Abstract. Candida albicans (C. albicans) is an opportunistic fungal pathogen, particularly observed in immunocompromised patients. C. albicans accounts for 50-70% of cases of invasive candidiasis in the majority of clinical settings. Terbinafine, an allylamine antifungal drug, has been used to treat fungal infections previously. It has fungistatic activity against C. albicans. Traditional Chinese medicines can be used as complementary medicines to conventional drugs to treat a variety of ailments and diseases. Berberine is a quaternary alkaloid isolated from the traditional Chinese herb, Coptidis Rhizoma, while berberrubine is isolated from the medicinal plant Berberis vulgaris, but is also readily derived from berberine by pyrolysis. The present study demonstrates the possible complementary use of berberine and berberrubine with terbinafine against C. albicans. The experimental findings assume that the potential application of these alkaloids together with reduced dosage of the standard drug would enhance the resulting antifungal potency.

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Section: Determination Of Mic and Minimum Fungicidal Concentration (Mmentioning

confidence: 99%

Sensitization of Candida albicans to terbinafine by berberine and berberrubine

et al. 2016

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“…We have previously reported a reaction for the preparation of 8-substituted quinoline ethers under basic condition in organic solvent with the help of phase transfer agent [ 14 ]. We now extended our reported protocol into a facile reaction in water for the substitution of 8-hydroxyquinoline (8HQ) and extended the protocol for various commercially available quinolines, such as 8-aminoquinoline (8AQ) and 2-methyl-8-hydroxyquinoline (8QD), to prepare the corresponding substituted quinolines for the study of substituent and linker (between quinoline core and sulfonyl group) effects on the biological activities towards cancer cells.…”

Section: Resultsmentioning

confidence: 99%

“…In particular, tropical plants, such as Galipea officinalis and Galipea longiflora , are naturally occurring sources of several important tetrahydroquinoline and quinoline alkaloids [ 11 ]. Extensive studies, including our reported work, demonstrated that quinoline derivatives have a wide range of biological activities [ 12 ] leading, for instance, to anticancer [ 13 ], antimicrobial [ 14 ], and anti-inflammatory effects [ 15 ].…”

Section: Introductionmentioning

confidence: 99%

Targeting DNA Binding for NF-κB as an Anticancer Approach in Hepatocellular Carcinoma

Chung

Lam

Zhou

et al. 2018

Cells

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Quinoline core has been shown to possess a promising role in the development of anticancer agents. However, the correlation between its broad spectrum of bioactivity and the underlying mechanism of actions is poorly understood. The present study, with the use of bioinformatics approaches, reported a series of designed molecules which integrated quinoline core and sulfonyl moiety, with the objective of evaluating the substituent and linker effects on anticancer activities and associated mechanistic targets. We identified potent compounds (1h, 2h, 5 and 8) exhibiting significant anticancer effects towards liver cancer cells (Hep3B) with the 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) relative values of cytotoxicity below 0.40, a value in the range of doxorubicin positive control with the value of 0.12. Bulky substituents and the presence of bromine atom, as well as the presence of sulfonamide linkage, are likely the favorable structural components for molecules exerting a strong anticancer effect. To the best of our knowledge, our findings obtained from chemical synthesis, in vitro cytotoxicity, bioinformatics-based molecular docking analysis (similarity ensemble approach, SEA),and electrophoretic mobility shift assay provided the first evidence in correlation to the anticancer activities of the selected compound 5 with the modulation on the binding of transcription factor NF-κB to its target DNA. Accordingly, compound 5 represented a lead structure for the development of quinoline-based NF-κB inhibitors and this work added novel information on the understanding of the mechanism of action for bioactive sulfonyl-containing quinoline compounds against hepatocellular carcinoma.

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“…Quinoline compounds have attracted great attention in the field of drug development [1][2][3][4][5][6][7]. In this sense, our research group has shown the synthesis and pharmacologic properties of new quinoline derivatives [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Further analysis of acute antinociceptive and anti‐inflammatory actions of 4‐phenylselenyl‐7‐chloroquinoline in mice

Silva

Reis

Pinz

et al. 2017

Fundamemntal Clinical Pharma

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A new quinoline containing selenium, 4-phenylselenyl-7-chloroquinoline (4-PSQ), was described and synthetized by our research group. Recently, we demonstrated the potential antinociceptive and anti-inflammatory of 4-PSQ. For this reason, the first objective of this study was to expand our previous findings by investigating the contribution of glutamatergic, serotonergic, and nitrergic systems to the acute antinociceptive action of this compound. Pretreatment with 4-PSQ (0.01-25 mg/kg, p.o.) reduced the nociception induced by glutamate. MK-801 (an uncompetitive antagonist of the N-Methyl-d-aspartate (NMDA) receptor) blocked the antinociceptive effect exerted by 4-PSQ (25 mg/kg, p.o.) in the acetic acid-induced abdominal writhing test. The pretreatment with WAY100635 (a selective antagonist of 5-HT receptor), ketanserin (a selective antagonist of 5-HT receptor), and pindolol (a nonselective antagonist of 5-HT receptors) partially blocked the antinociceptive effect caused by 4-PSQ (25 mg/kg, per oral, p.o.) in the acetic acid-induced abdominal writhing test. Nitric oxide precursor, l-arginine hydrochloride, partially reversed antinociception caused by 4-PSQ or ω-nitro-l-arginine (l-NOARG). Treatments did not modify the locomotor and exploratory activities of mice. Additionally, the acute anti-inflammatory effect of 4-PSQ in a model of pleurisy induced by carrageenan in mice was investigated. 4-PSQ reduced the cellular migration, pleural exudate accumulation, and myeloperoxidase activity induced by carrageenan exposure. 4-PSQ protected against the increase in reactive species levels and reduction of nonprotein thiol levels induced by carrageenan. Data presented here showed that the modulation of serotonergic, nitrergic, and glutamatergic systems contributed to the antinociceptive effect of 4-PSQ and it reinforced the therapeutic potential of this quinolinic compound for acute inflammation.

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Development of 8-benzyloxy-substituted quinoline ethers and evaluation of their antimicrobial activities

Cited by 11 publications

References 40 publications

Sensitization of Candida albicans to terbinafine by berberine and berberrubine

Sensitization of Candida albicans to terbinafine by berberine and berberrubine

Targeting DNA Binding for NF-κB as an Anticancer Approach in Hepatocellular Carcinoma

Further analysis of acute antinociceptive and anti‐inflammatory actions of 4‐phenylselenyl‐7‐chloroquinoline in mice

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