Efficacy of 2-hydroxy-3-phenylsulfanylmethyl-[1,4]-naphthoquinone derivatives against different Trypanosoma cruzi discrete type units: Identification of a promising hit compound

Lara, L.S.; Moreira, Caroline S.; Calvet, Cláudia M.; Lechuga, Guilherme Curty; Souza, Raquel Santos; Bourguignon, Saulo Cabral; Ferreira, Vı́tor F.; Rocha, David R. da; Pereira, Mirian Cláudia de Souza

doi:10.1016/j.ejmech.2017.12.052

Cited by 39 publications

(19 citation statements)

References 60 publications

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“…[4,5] Notably,1 ,4-naphthoquinonesg raftedw ith an amino or substituted amino group at the 2-position have been potential candidates in medical and biological applications. Furthermore, recent researchh as demonstrated that these molecules exhibit antitubercular, [6] antimalarial, [7] trypanocidal, [8] anticancer, [9] and antimicrobial [10] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

et al. 2019

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1,4‐Naphthoquinones are exceptional building blocks in organic synthesis and have been used to synthesize several well‐known pharmaceutically active agents. Herein we report the synthesis, structural characterization, and biological evaluation of new phenylaminosulfanyl‐1,4‐naphthoquinone derivatives. We evaluated the cytotoxic activity of the synthesized compounds against three human cancer cell lines: A549, HeLa, and MCF‐7. Most of the synthesized compounds displayed potent cytotoxic activity. Specifically, compounds 5 e [3,5‐dichloro‐N‐(4‐((4‐((1,4‐dioxo‐3‐(phenylthio)‐1,4‐dihydronaphthalen‐2‐yl)amino)phenyl)sulfonyl)phenyl)benzamide], 5 f [N‐(4‐((4‐((1,4‐dioxo‐3‐(phenylthio)‐1,4‐dihydronaphthalen‐2‐yl)amino)phenyl)sulfonyl)phenyl)‐3,5‐dinitrobenzamide], and 5 p [N‐(4‐((4‐((1,4‐dioxo‐3‐(phenylthio)‐1,4‐dihydronaphthalen‐2‐yl)amino)phenyl)sulfonyl)phenyl)thiophene‐2‐carboxamide] showed remarkable cytotoxic activity. The synthesized compounds showed low toxicity in normal human kidney HEK293 cells. The cytotoxic mechanism of compounds 5 e, 5 f, and 5 p was explored in MCF‐7 cells. The results confirmed that these three compounds induce apoptosis and arrest the cell cycle at the G1 phase. In addition, compounds 5 e, 5 f, and 5 p were found to induce apoptosis via upregulation of caspase‐3 and caspase‐7 proteins as well as by upregulation of the gene expression levels of caspases‐3 and ‐7. Our findings demonstrate that compounds 5 e, 5 f, and 5 p could be potent agents against a number of cancer types.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

et al. 2019

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“…[7,8] 1,4-Naphthoquinones and its related compounds are well-established for irreversible complexation during ROS generation in proteins, which leads to loss of protein function. [9] Due to these properties, 1,4-naphthoquinone derivatives exhibit biological properties such as antimicrobial, [10] antimalarial, [11] antitubercular, [12] anticancer, [13] and trypanocidal [14] activities.…”

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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“…83) A new series of 1,4-naphthoquinones, bearing various cyclic and aliphatic amines at 2-position, were designed and synthesized to identify antiproliferative agents for triple-negative breast cancer. Among them two compounds (64)(65) (Fig. 16) significantly inhibited in vitro the proliferation of MDA-MB-231 cells.…”

Section: Cardioprotective and Anti-ischemic Propertiesmentioning

confidence: 98%

“…In subsequent studies, the biologically active nucleus of natural quinones was modified by organic synthesis 63,64) and the newly obtained biologically active derivatives of these 1,4-naphthoquinones were patented. 65) The efficacy of a series of 2-hydroxy-3-phenylsulfanylmethyl- [ (46) (Fig. 11) showed higher susceptibility to bloodstream trypomastigotes and exhibited a greater efficacy against trypomastigotes from different T. cruzi of Brazil and CL strains through the induction of intracellular autophagy and elevation of ROS level, leading to parasite death.…”

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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Efficacy of 2-hydroxy-3-phenylsulfanylmethyl-[1,4]-naphthoquinone derivatives against different Trypanosoma cruzi discrete type units: Identification of a promising hit compound

Cited by 39 publications

References 60 publications

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

Synthesis and Anticancer Evaluation of 1,4‐Naphthoquinone Derivatives Containing a Phenylaminosulfanyl Moiety

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

1,4-Naphthoquinones: Some Biological Properties and Application

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