Biological activity of 1,2,3-triazole-2-amino-1,4-naphthoquinone derivatives and their evaluation as therapeutic strategy for malaria control

Souza, Renata Maria Costa; Pimentel, Lílian Maria Lapa Montenegro; Ferreira, Laryssa Kathleen Mendonça; Pereira, Valéria Rêgo Alves; Santos, Aline Caroline da Silva; Dantas, Willyenne Marília; Silva, Carla Jasmine Oliveira; Brito, Ramayana Morais de Medeiros; Andrade, José Lucas; Andrade‐Neto, Valter Ferreira de; Fujiwara, Ricardo Toshio; Bueno, Lilian Lacerda; Silva, Valdemiro Da; Pena, Lindomar; Câmara, Celso A.; Rathi, Brijesh; Oliveira, Ronaldo N. de

doi:10.1016/j.ejmech.2023.115400

Cited by 11 publications

(1 citation statement)

References 60 publications

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“…Modifying 1,4-naphthoquinone moiety at the C2 and C3 positions leads to obtaining a new compound with high biological activity. The pharmacokinetic research showed that the synthetic derivatives exhibit good solubility and bioavailability [ 18 , 19 , 20 , 21 , 22 ].…”

Section: Introductionmentioning

confidence: 99%

Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives: Synthesis, Anticancer Activity, and Molecular Docking Study

Kadela-Tomanek,

Krzykawski,

Halama

et al. 2023

Molecules

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One of the most essential health problems is cancer, the first or second cause of death worldwide. Head and neck cancers are hard to detect due to non-specific symptoms. The treatment often relies on a combination of radio and chemotherapy. For this reason, the research of new anticancer compounds is fundamental. The natural and synthetic compounds with 1,4-naphthoquinone scaffold is characterized by high anticancer activity. The study aimed to evaluate the synthesis and anticancer activity of hybrids 1,4-naphthoquinone with thymidine derivatives. The series of compounds allows us to check the influence of the substituent in the C3′ position of the thymidine moiety on the cytotoxicity against squamous cancer cell lines (SCC-9 and SCC-25) and submandibular gland cancer (A-253). An annexin V/propidium iodide (PI) co-staining assay shows that derivatives cause the apoptotic in SCC-25 and A-253 cell lines. The molecular docking study examined the interaction between the active site of the BCL-2 protein and the hybrids.

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Section: Introductionmentioning

confidence: 99%

Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives: Synthesis, Anticancer Activity, and Molecular Docking Study

Kadela-Tomanek,

Krzykawski,

Halama

et al. 2023

Molecules

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Exploring the Recent Pioneering Developments of Small Molecules in Antimalarial Drug Armamentarium: A Chemistry Prospective Appraisal

Bagratee,

Prawlall,

Ndlovu

et al. 2024

Chemistry & Biodiversity

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Malaria is a very destructive and lethal parasitic disease that causes significant mortality worldwide, resulting in the loss of millions of lives annually. The uncontrolled intake of antimalarial drugs often employed in clinical settings has resulted in the emergence of numerous strains of plasmodium that are resistant to these drugs, including multidrug‐resistant strains. Hence, there is an urgent need for developing unique classes of antimalarial drugs that function with distinct mechanisms of action. In this context, the design and development of hybrid compounds that combine pharmacophoric properties from different lead molecules into a single unit gives a unique perspective towards further development of malaria drugs in the next generation. In light of this, we have reviewed the progress of hybrid antimalarial agents from 2021 up to the present. This manuscript presents a comprehensive overview of the latest advancements in the medicinal chemistry pertaining to small molecules, with a specific focus on their potential as antimalarial agents. This review explores a variety of physiologically active compounds that have been described in the literature in order to lay a strong foundation for the logical design and eventual identification of antimalarial drugs based on lead frameworks.

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In Vitro and In Vivo Biological Evaluation of Novel 1,4‐Naphthoquinone Derivatives as Potential Anticancer Agents

Ravichandiran,

Martyna,

Kochanowicz

et al. 2024

ChemMedChem

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A novel library of naphthoquinone derivatives (3–5aa) was synthesized and evaluated for their anticancer properties. Specifically, compounds 5i, 5l, 5o, 5q, 5r, 5s, 5t, and 5v demonstrated superior cytotoxic activity against the cancer cell lines that were studied. Notably, compound 5v displayed a greater cytotoxic effect on MCF‐7 cells compared to the standard drug doxorubicin. To further investigate the mechanism of cytotoxic effect, additional anticancer studies were conducted with 5v in MCF‐7 cells. The findings showed that 5v triggered cytotoxic effects in MCF‐7 cells through the initiation of cell cycle arrest at the G1/S phase and necrosis. In vivo ecotoxicity studies indicated that 5v had lower toxicity towards zebrafish larvae (LC50 = 50.15 μM) and had an insignificant impact on cardiac functions. In vivo xenotransplantation of MCF‐7 cells in zebrafish larvae demonstrated a significant reduction in tumour volume in the xenograft. Approximately 95% of the zebrafish larvae with 5v xenografts survived after 10 days of the treatment. Finally, a computational modelling study was conducted on four protein receptors, namely ER, EFGR, BRCA1, and VEFGR2. The findings highlight the importance of the aminonaphthoquinone moiety, amide linkage, and propyl thio moiety in enhancing the anticancer properties.

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Biological activity of 1,2,3-triazole-2-amino-1,4-naphthoquinone derivatives and their evaluation as therapeutic strategy for malaria control

Cited by 11 publications

References 60 publications

Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives: Synthesis, Anticancer Activity, and Molecular Docking Study

Hybrids of 1,4-Naphthoquinone with Thymidine Derivatives: Synthesis, Anticancer Activity, and Molecular Docking Study

Exploring the Recent Pioneering Developments of Small Molecules in Antimalarial Drug Armamentarium: A Chemistry Prospective Appraisal

In Vitro and In Vivo Biological Evaluation of Novel 1,4‐Naphthoquinone Derivatives as Potential Anticancer Agents

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