Novel NO-releasing plumbagin derivatives: Design, synthesis and evaluation of antiproliferative activity

Bao, Na; Ou, Jinfeng; Xu, Manyi; Guan, Fuqin; Shi, Wei; Sun, Jianbo

doi:10.1016/j.ejmech.2017.05.046

Cited by 22 publications

(5 citation statements)

References 16 publications

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“…In particular, hybrids 31a,b (IC 50 : 1.73–4.54 μ M) were found to be most active and could act as lead compounds for further modifications. The furoxan‐plumbagin hybrids 32a,b (IC 50 : 1.21–3.33 μ M, MTT assay) showed considerable activity against MDA‐MB‐231 and HepG2 cancer cell lines, but the activity was lower than that of napabucasin (IC 50 : 0.34 and 0.66 μ M) [56].…”

Section: Miscellaneous Furoxan Hybridsmentioning

confidence: 99%

The current scenario of furoxan hybrids with anticancer potential

Shi

Wang

Yan³

2023

Journal of Heterocyclic Chem

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Cancer is one of the most common and deadliest diseases affecting millions of human beings globally. Treatment of cancer has achieved great advancements, and chemotherapy remains one of the most important means. However, the chemotherapy suffers from apparent limitations including drug resistance, systemic toxicity, adverse effects, and tumor recurrence, creating an urgent demand to develop novel anticancer chemotherapeutics. Furoxan derivatives could exert anticancer activity via releasing high concentrations of nitric oxide (NO), which could induce cellular apoptosis, arrest cell cycle, inhibit the migration and invasion of cells, and suppress angiogenesis. Hence, furoxan derivatives demonstrated potent in vitro and in vivo anticancer efficiency. In particular, furoxan hybrids, combination of other anticancer pharmacophores with furoxan moiety, demonstrated significant therapeutic effects on various cancers including drug‐resistant forms since these derivatives could act on multiple targets in cancer cells simultaneously. Accordingly, furoxan hybrids constitute an important source in the development of novel chemotherapeutic agents with anticancer activity. This review is to highlight the current scenario of furoxan hybrids with anticancer potential, covering articles published from 2012 to present. The structure–activity relationships and mechanisms of action are discussed to continuously open up a map for the remarkable exploration of more effective candidates.

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Section: Miscellaneous Furoxan Hybridsmentioning

confidence: 99%

The current scenario of furoxan hybrids with anticancer potential

Shi

Wang

Yan³

2023

Journal of Heterocyclic Chem

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“…[21] Plumbagin (3) is a naphthoquinone analog widely distributed in various plants, including Iridaceae, Plumbaginaceae, Ebenceae, Drosophyllaceae, Nepenthaceae, and Droseraceae, [22] and exhibits highly potent bioactivities. [23] Lapachol (4), a natural pigment, is the main constituent of Stereospermum sueovelens DC (Bignoni-aceae), [24] and its conversion into various derivatives also have similar biological activity. Shikonin ( 5) is also a 1,4-NQ derivative, isolated from traditional medicinal plant species of the genus Lithospermum, Alkanna, Arnebia, Anchusa, Onosma, and Echium belonging to the Boraginaceae family.…”

Section: Natural 14-nq Analogsmentioning

confidence: 99%

1,4‐Naphthoquinone Analogs and Their Application as Antibacterial Agents

2022

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Antimicrobial resistance threatens the effective prevention and treatment of an ever‐increasing range of infections caused by different types of bacteria. Addressing antibacterial resistance and protecting human health requires multi‐sectoral, long‐acting, and professional administration. Sustainable investment in the R&D of antimicrobial drugs is one of the critical strategies for solving the current problem. Specifically, the development of novel effective drug candidates with a unique mode of action is essential for overcoming antibacterial resistance. 1,4‐Naphthoquinone is a quinone derivative from naphthalene, one of the most important subclasses of quinone. 1,4‐Naphthoquinones have been studied as potential candidates against various diseases, including cancer and malaria, and are a promising new compound that can treat bacterial infections. This review focuses on 1,4‐naphthoquinone analogs for their activity against bacteria.

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“…Particularly, furoxans could induce ferroptosis of tumor cells by covalently inhibiting glutathione peroxidase 4 (GPX4) . These profiles of furoxans made them be widely used in synthesis of antitumor compounds based on a hybridization strategy, which could achieve a synergistic therapeutic effect, overcome drug resistance, and reduce toxicity …”

Section: Introductionmentioning

confidence: 99%

“…24 (GPX4). 25 These profiles of furoxans made them be widely used in synthesis of antitumor compounds based on a hybridization strategy, 26 which could achieve a synergistic therapeutic effect, 27 overcome drug resistance, 28 and reduce toxicity. 29 In this study, a total of twenty-eight NOD-AVB conjugates were designed and synthesized based on a hybridization strategy.…”

Section: Introductionmentioning

confidence: 99%

Discovery of NO Donor-Aurovertin Hybrids as Dual Ferroptosis and Apoptosis Inducers for Treating Triple Negative Breast Cancer

Ma,

Xu,

Yuan

et al. 2024

J. Med. Chem.

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Triple-negative breast cancer (TNBC) is a highly lethal malignancy, and its clinical management encounters severe challenges due to its high metastatic propensity and the absence of effective therapeutic targets. To improve druggability of aurovertin B (AVB), a natural polyketide with a significant antiproliferative effect on TNBC, a series of NO donor/AVB hybrids were synthesized and tested for bioactivities. Among them, compound 4d significantly inhibited the proliferation and metastasis of TNBC in vitro and in vivo with better safety than that of AVB. The structure−activity relationship analysis suggested that the types of NO donor and the linkers had considerable effects on the activities. Mechanistic investigations unveiled that 4d induced apoptosis and ferroptosis by the reduction of mitochondrial membrane potential and the down-regulation of GPX4, respectively. The antimetastatic effect of 4d was associated with the upregulation of DUSP1. Overall, these compelling results underscore the tremendous potential of 4d for treating TNBC.

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Novel NO-releasing plumbagin derivatives: Design, synthesis and evaluation of antiproliferative activity

Cited by 22 publications

References 16 publications

The current scenario of furoxan hybrids with anticancer potential

The current scenario of furoxan hybrids with anticancer potential

1,4‐Naphthoquinone Analogs and Their Application as Antibacterial Agents

Discovery of NO Donor-Aurovertin Hybrids as Dual Ferroptosis and Apoptosis Inducers for Treating Triple Negative Breast Cancer

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