Synthesis and Cytotoxic Evaluation of a Series of  2-Amino-Naphthoquinones against Human Cancer Cells

Moraes, Thiago Augusto Pereira de; Filha, Maria J. S.; Câmara, Celso A.; Silva, Tania M. S.; Soares, Bruno Moreira; Bomfim, Igor S.; Pessoa, Cláudia; Ximenes, George C.; Silva, Valdemiro A.

doi:10.3390/molecules190913188

Cited by 29 publications

(27 citation statements)

References 29 publications

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“…The compounds used in this study ( Figure 1) are novel, synthetically-derived polycyclic aromatic hydrocarbons, belonging to the aminonaphthoquinone class of compounds (coded Rau 008, Rau 010, Rau 015 and Rau 018). Aminonaphthoquinones have shown potential as anti-cancer agents (28,29). In particular, the cytotoxicity of Rau 010 and Rau 018 was assayed against cervical carcinoma (HeLa) and T-cell leukaemia (Jurkat) cells and it was found that these aminonaphthoquinones showed significant anti-proliferative activity against both cell lines (29).…”

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confidence: 99%

Evaluation of the Effects of Aminonaphthoquinone Derivatives in Combination with Curcumin Against ER-positive Breast Cancer and Related Tumours

Pereira

Mohammed

Otterlo

et al. 2017

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mentioning

confidence: 99%

Evaluation of the Effects of Aminonaphthoquinone Derivatives in Combination with Curcumin Against ER-positive Breast Cancer and Related Tumours

Pereira

Mohammed

Otterlo

et al. 2017

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“…Cytotoxic activity of 4'-leucinoavarone was recently studied in more details [44,45]. (peripheral blood mononuclear cells) [46]. For this type of compounds, glycine, alanine and phenylalanine derivatives showed a better activity than β-alanine and proline ones.…”

Section: Fig 3 Tautomeric Forms Of Avarone and Tert-butylquinone Dementioning

confidence: 98%

Synthesis and biological activity of amino acid derivatives of avarone and its model compound

Vilipić

Novaković

Stanojković

et al. 2015

Bioorganic & Medicinal Chemistry

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A series of eighteen derivatives of marine sesquiterpene quinone avarone and its model system tert-butylquinone with amino acids has been synthesized by nucleophilic addition of amino acids to the quinones. In vitro cytotoxic activity toward human cancer cell lines (HeLa, A549, Fem-X, K562, MDA-MB-453) and normal MRC-5 cell line was determined. Several compounds showed very strong inhibitory activity with IC50 values less than 10 μM. Avarone derivatives were more active than the corresponding tert-butylquinone derivatives. The results of the cytofluorimetric analysis of cell cycle of HeLa cells showed that apoptosis might be one of possible mechanism of action of these compounds in cancer cells. In order to examine the influence of caspases on cell death, the apoptotic mechanisms induced by the tested compounds were determined using specific caspases 3, 8 and 9 inhibitors. For all compounds antibacterial activities against six strains of Gram-positive and four strains of Gram-negative bacteria were determined, as well as antifungal activity against three fungal species.

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“…The mechanism of fighting against microorganisms using amino-naphthoquinones has been elucidated in detail in a previous publication [8][9][10]. In brief, the amino-naphthoquinones inhibits growth of microorganisms by using an electrochemical mode of action to penetrate and disrupt their essential structures.…”

Section: Investigation Of the Treated Oxidation Cotton Fabric With Namentioning

confidence: 99%

Use of amino-naphthoquinones for production of antimicrobial textiles

Li¹

2016

Funct.Mater.

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This study described a method for enhancing the durability of amino-naphthoquinones embedded on cotton fabrics by creating aldehyde groups in the molecular structure of cotton cellulose. These aldehyde groups undergo intermolecular coupling with the amino group to form imines whereby naphthoquinones are covalently bonded to the cotton cellulose. The results suggest that these antibacterial compounds are tightly bound to the cotton fabric and impart to the fabric antibacterial properties, which retain their antibacterial activity after 15 laundry cycles. Such type of antimicrobial finish can find wide application in the health and hygiene textile sector.Описан способ повышения устойчивости аминонафтохинов, входящих в хлопковые ткани, путем создания альдегидных групп в молекулярной структуре хлопковой целлюлозы. Полученные результаты свидетельствуют о том, что указанные антибактериальные соединения тесно связаны с хлопковой тканью, они придают ткани антибактериальные свойства, которые сохраняют свою антибактериальную активность даже после 15 циклов обработки. Такой тип антибактериальной обработки может найти широкое применение в здравоохранении и в гигиеническом секторе текстильной отрасли.Використання амінонафтохінонів для виробництва антибактеріального текстилю. Хун Лі, Чао Дін, Інг Чао Лі, Ін Ван, Цю Хун Ван В роботі описано спосіб підвищення міцності вбудованих в бавовняні тканини амінонафтохінонов шляхом створення альдегідних груп в молекулярній структурі бавовняної целюлози. Отримані результати свідчать про те, що зазначені антибактеріальні сполуки тісно зв'язані з бавовняною тканиною, вони надають тканині антибактеріальні властивості, які зберігають свою антибактеріальну активність навіть після 15 циклів обробки. Такий тип антибактеріальної обробки може знайти широке застосування в охороні здоров'я і в гігієнічному секторі текстильної галузі.

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Synthesis and Cytotoxic Evaluation of a Series of 2-Amino-Naphthoquinones against Human Cancer Cells

Abstract: ) than values shown by tumour cell lines. The mechanism of cell growth inhibition and structure-activity relationships remains as a target for future investigations.

Cited by 29 publications

References 29 publications

Evaluation of the Effects of Aminonaphthoquinone Derivatives in Combination with Curcumin Against ER-positive Breast Cancer and Related Tumours

Evaluation of the Effects of Aminonaphthoquinone Derivatives in Combination with Curcumin Against ER-positive Breast Cancer and Related Tumours

Synthesis and biological activity of amino acid derivatives of avarone and its model compound

Use of amino-naphthoquinones for production of antimicrobial textiles

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