Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides

Kos, Jiří; Nevin, Eoghan; Šoral, Michal; Kushkevych, Ivan; Goněc, Tomáš; Bobáľ, Pavel; Kollár, Péter; Coffey, Aidan; O’Mahony, Jim; Liptaj, Tibor; Kráľová, Katarína; Jampílek, Josef

doi:10.1016/j.bmc.2015.03.018

Cited by 43 publications

(47 citation statements)

References 34 publications

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“…Similar effects were observed previously, for example, with ring-substituted 6-hydroxynaphthalene-2-carboxanilides, where 3-Cl, 4-Cl, 3-Br, and 3-CF 3 substituted derivatives decreased the viability of M. tuberculosis H37Ra in the range from 41.2% to 46.5% at the lowest tested concentration (MICs = 8 µg/mL) [20], with 8-hydroxy- N -(3-trifluoromethylphenyl)quinoline-2-carbox-amide, where the decrease of the viability of M. tuberculosis H37Ra was to 18.8% at MIC = 8 µg/mL [60], and with N -alkoxyphenylhydroxynaphthalenecarboxanilides substituted in C (3) ’ position of the anilide core by a longer alkoxy tail [61,62]. Since the MTT assay was positive, it can be stated that the tested compounds caused a decrease of mycobacterial cell metabolism.…”

Section: Resultssupporting

confidence: 85%

“…The preliminary in vitro screening of the antiproliferative activity of the most effective antimicrobial compounds was performed using a Water Soluble Tetrazolium salts-1 (WST-1) assay kit [78] and the human monocytic leukemia THP-1 cell line by means of the method described recently [20,79]. The principle of the WST-1 assay kit is that antiproliferative compounds inhibit mitochondrial dehydrogenases.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds were designed based on the experience with naphthalenecarboxamides—simple molecules with a number of biological activities, and in fact, the new ring-substituted (2 E )- N -phenyl-3-phenylprop-2-enamides can be considered as open analogues of recently described naphthalene-2-carboxanilides [19,20]. …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides

Pospíšilová

Kos

Michnová

et al. 2018

IJMS

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A series of sixteen ring-substituted N-arylcinnamamides was prepared and characterized. Primary in vitro screening of all the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra, Fusarium avenaceum, and Bipolaris sorokiniana. Several of the tested compounds showed antistaphylococcal, antitubercular, and antifungal activities comparable with or higher than those of ampicillin, isoniazid, and benomyl. (2E)-N-[3,5-bis(trifluoromethyl)phenyl]-3-phenylprop-2-enamide and (2E)-3-phenyl-N-[3-(trifluoromethyl)phenyl]prop-2-enamide showed the highest activities (MICs = 22.27 and 27.47 µM, respectively) against all four staphylococcal strains and against M. tuberculosis. These compounds showed an activity against biofilm formation of S. aureus ATCC 29213 in concentrations close to MICs and an ability to increase the activity of clinically used antibiotics with different mechanisms of action (vancomycin, ciprofloxacin, and tetracycline). In time-kill studies, a decrease of CFU/mL of >99% after 8 h from the beginning of incubation was observed. (2E)-N-(3,5-Dichlorophenyl)- and (2E)-N-(3,4-dichlorophenyl)-3-phenylprop-2-enamide had a MIC = 27.38 µM against M. tuberculosis, while a significant decrease (22.65%) of mycobacterial cell metabolism determined by the MTT assay was observed for the 3,5-dichlorophenyl derivative. (2E)-N-(3-Fluorophenyl)- and (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide exhibited MICs = 16.58 and 33.71 µM, respectively, against B. sorokiniana. The screening of the cytotoxicity of the most effective antimicrobial compounds was performed using THP-1 cells, and these chosen compounds did not shown any significant lethal effect. The compounds were also evaluated for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. (2E)-N-(3,5-dichlorophenyl)-3-phenylprop-2-enamide (IC50 = 5.1 µM) was the most active PET inhibitor. Compounds with fungicide potency did not show any in vivo toxicity against Nicotiana tabacum var. Samsun. The structure–activity relationships are discussed.

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Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides

Pospíšilová

Kos

Michnová

et al. 2018

IJMS

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“…One possible explanation was the first-line anti-tuberculosis drugs might directly or indirectly interfere the enzymes in the vitamin D metabolism pathway such as CYP27A1 or CYP24A1 which may interfere with the activation of the vitamin D receptor in macrophages. Another limitation is the concentrations of the anti-TBs were based on the minimal inhibitory concentration (MIC) from published in vitro THP-1 cell culture and TB experiments in the literature [25], [26], [27], [28]. Also our THP-1 cells were not infected by Mtb .…”

Section: Discussionmentioning

confidence: 99%

“…The concentrations of each drug were examined over a range of doses known to inhibit Mtb growth from previously published studies [24], [25], [26], [27], [28], [29] at a final concentration of 1.0 µg/mL, 5.0 µg/mL and 10.0 µg/mL. THP-1 cells were then incubated in 37 °C, 5% CO 2 for 6 hours, following which cell suspensions were centrifuged and supernatants removed.…”

Section: Methodsmentioning

confidence: 99%

The effects of first-line anti-tuberculosis drugs on the actions of vitamin D in human macrophages

Chesdachai

Zughaier

et al. 2016

Journal of Clinical & Translational Endocrinology

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Tuberculosis (TB) is a major global health problem. Patients with TB have a high rate of vitamin D deficiency, both at diagnosis and during the course of treatment with anti-tuberculosis drugs. Although data on the efficacy of vitamin D supplementation on Mycobacterium tuberculosis (Mtb) clearance is uncertain from randomized controlled trials (RCTs), vitamin D enhances the expression of the anti-microbial peptide human cathelicidin (hCAP18) in cultured macrophages in vitro. One possible explanation for the mixed (primarily negative) results of RCTs examining vitamin D treatment in TB infection is that anti-TB drugs given to enrolled subjects may impact actions of vitamin D to enhance cathelicidin in macrophages. To address this hypothesis, human macrophage-like monocytic (THP-1) cells were treated with varying doses of first-line anti-tuberculosis drugs in the presence of the active form of vitamin D, 1N1,25-dihydroxyvitamin D3 (1,25(OH)2D3). The expression of hCAP18 was determined by quantitative reverse transcriptase polymerase chain reaction (qRT-PCR). 1,25(OH)2D3 strongly induced expression of hCAP18 mRNA in THP-1 cells (fold-change from control). The combination of the standard 4-drug TB therapy (isoniazid, rifampicin, pyrazinamide and ethambutol) in the cultured THP-1 cells demonstrated a significant decrease of hCAP18 mRNA at the dosage of 10 ug/mL. In 31 subjects with newly diagnosed drug-sensitive TB randomized to either high-dose vitamin D3 (1.2 million IU over 8 weeks, n=13) versus placebo (n=18), there was no change from baseline to week 8 in hCAP18 mRNA levels in peripheral blood mononuclear cells or in plasma concentrations of LL-37, the protein product of hCAP18.These data suggest that first-line anti-TB drugs may alter the vitamin D-dependent increase in hCAP18 and LL-37 human macrophages.

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Voltammetry of a Novel Antimycobacterial Agent 1‐Hydroxy‐N‐(4‐nitrophenyl)naphthalene‐2‐carboxamide in a Single Drop of a Solution

et al. 2017

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The aim of this study is the development of a miniaturized voltammetric method for the determination of an antimycobacterial agent 1-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide (HNN) in a single drop (20 mL) of a solution by cathodic and anodic voltammetry at a glassy carbon electrode. Cyclic voltammetry was used to investigate its redox properties followed by the optimization of differential pulse voltammetric determination in a regular 10 mL volume. The optimal medium for the analytical application of both cathodic and anodic voltammetry was found to be Britton-Robinson buffer pH 7.0 and dimethyl sulfoxide (9 : 1, v/v). HNN gave one cathodic peak at around À0.6 V and one anodic peak at around + 0.2 V vs. Ag j AgCl (3 mol L À1 KCl) reference electrode. Determination of HNN in a 10 mL volume gave the limit of quantification around 10 nmol L À1 by both adsorptive stripping anodic and cathodic voltammetry. Afterwards, miniaturized voltammetric methods in a single drop of solution (20 mL) were investigated. This approach requested some modifications of the cell design and voltammetric procedures. A novel method of removing dissolved oxygen in a single drop had to be developed and tested. Developed miniaturized voltammetric methods gave parameters comparable to the determination of HNN in 10 mL. The applicability of the miniaturized method was verified by the determination of HNN in a drop of a bacterial growth medium.

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Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides

Cited by 43 publications

References 34 publications

Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides

Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides

The effects of first-line anti-tuberculosis drugs on the actions of vitamin D in human macrophages

Voltammetry of a Novel Antimycobacterial Agent 1‐Hydroxy‐N‐(4‐nitrophenyl)naphthalene‐2‐carboxamide in a Single Drop of a Solution

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