Antibacterial naphthoquinone derivatives targeting resistant strain Gram-negative bacteria in biofilms

Novais, Juliana S.; Moreira, Caroline S.; Silva, Ana Carolina J. A.; Loureiro, Raquel S.; Figueiredo, Agnes Marie Sá; Ferreira, Vı́tor F.; Castro, Helena C.; Rocha, David R. da

doi:10.1016/j.micpath.2018.03.024

Cited by 40 publications

(18 citation statements)

References 80 publications

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“…Tandon et al [20,21] described the synthesis and biological evaluation of several new sulfanyl aminonaphthoquinones (compounds IV and V) that displayed important antibacterial activity. Novais et al [22] also reported 1,4-naphthoquinone-based sulfanyl derivatives, and their resistance toward Gram-negative bacteria in biofilms was investigated (compound VI). However, the detailed toxicity and action mechanism for these reported naphthoquinones in humans are unknown to date (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Ravichandiran

Masłyk

Sheet³

et al. 2019

ChemistryOpen

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1,4‐Naphthoquinones are an important class of compounds present in a number of natural products. In this study, a new series of 1,4‐naphthoquinone derivatives were synthesized. All the synthesized compounds were tested for in vitro antimicrobial activity. In this present investigation, two Gram‐positive and five Gram‐negative bacterial strains and one pathogenic yeast strain were used to determine the antibacterial activity. Naphthoquinones tested for its antibacterial potencies, among seven of them displayed better antimicrobial activity against Staphylococcus aureus ( S. aureus ; 30–70 μg/mL). Some of the tested compounds showed moderate to low antimicrobial activity against Pseudomonas aeruginosa ( P. aeruginosa ) and Salmonella bongori ( S. bongori ; 70–150 μg/mL). In addition, most active compounds against S. aureus were evaluated for toxicity to human blood cells using a hemolysis assay. For better understanding, reactive oxygen species (ROS) generation, time‐kill kinetic study, and apoptosis, necrosis responses were investigated for three representative compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Ravichandiran

Masłyk

Sheet³

et al. 2019

ChemistryOpen

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“…Naphthoquinones are a kind of common natural compounds, which have bactericidal, anti-oxidant and antiviral effects (Zhivetyeva et al, 2016;Novais et al, 2018). Some studies have shown that naphthoquinone derivatives have anti-tumor and apoptosis-inducing effects (Li et al, 2017;Liu et al, 2018).…”

Section: Discussionmentioning

confidence: 99%

A potential estrogen receptor inhibitor compound 34 induces apoptosis via ROS-independent intrinsic apoptosis in MCF-7 cells

Ding

Zhu

Teng

et al. 2019

Bangladesh J Pharmacol

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This study aimed to investigate the anti-tumor effects of compound 34 on MCF-7 cells in vitro, and explore its mechanisms. MTT results showed that compound 34 selectively inhibited estrogen receptor-positive cells proliferation. Hoechst 33342 staining showed nuclear pyknosis, nuclear debris associated with apoptotic bodies. JC-1 staining showed the loss of mitochondrial membrane potential. Although compound 34 increased intracellular reactive oxygen species (ROS), compound 34-induced apoptosis was not prevented by pretreatment with ROS scavengers. Western blotting showed apoptosis-related protein like cytochrome c and cleaved PARP protein increased. Furthermore, docking studies exhibited that compound 34 could bind into ERα. In summary, compound 34 selectively inhibited estrogen receptor positive cells proliferation and induced apoptosis in MCF-7 cells via ROS-independent intrinsic apoptosis in MCF-7 cells. It may be a potential targeted drug of estrogen receptor for therapeutic application of breast cancer. Video Clip of Methodology: Assay of Cell Proliferation: 5 min 5 sec Full Screen Alternate

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“…9) improved the inhibition of biofilm formation by more than 60% with a better profile than the standard antibacterial drug, ciprofloxacin. 53,54) 1,4-Naphthoquinone derivatives were found to significantly affect some fungal strains and suppress various bacteria growth, hyphal formation and cell aggregation. 55) A series of novel, substituted 2-chloro-3-[(thiazol-2-yl)amino]-1,4-naphthoquinones (30)(31)(32)(33)(34)(35)(36) (Fig.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 99%

1,4-Naphthoquinones: Some Biological Properties and Application

2020

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Over the past decade, a number of new 1,4-naphthoquinones have been isolated from natural sources and new 1,4-naphthoquinones with diverse structural features have been synthesized. Cardioprotective, antiischemic, hepatoprotective, neuroprotective and some other new properties were found for these compounds; their role in protecting against neurodegenerative diseases has been established. Their anti-inflammatory, antimicrobial and antitumor activities have been studied in more detail; new, previously unknown intracellular molecular targets and mechanisms of action have been discovered. Some compounds of this class are already being used as a medicinal drugs and some substances can be used as biochemical tools and probes for non-invasive detection of pathological areas in cells and tissues in myocardial infarction and neurodegenerative diseases using modern molecular imaging techniques.

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Antibacterial naphthoquinone derivatives targeting resistant strain Gram-negative bacteria in biofilms

Cited by 40 publications

References 80 publications

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

Synthesis and Antimicrobial Evaluation of 1,4‐Naphthoquinone Derivatives as Potential Antibacterial Agents

A potential estrogen receptor inhibitor compound 34 induces apoptosis via ROS-independent intrinsic apoptosis in MCF-7 cells

1,4-Naphthoquinones: Some Biological Properties and Application

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