Crystal structure of 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione

Isidório, Raquel Geralda; Melo, Ottoni Flaviano; José, Alves Ricardo; Lúcio, Speziali Nivaldo

doi:10.1107/s2056989018011647

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“…Lawsone was purchased from Sigma-Aldrich Brazil, São Paulo. Compounds 1 [ 20 ], 4 [ 21 ] and 9–16 [ 22 ] were prepared according to literature. Data regarding the synthesis and characterization of compounds 2, 3 and 5–8 are described in Additional file 1 .…”

Section: Methodsmentioning

confidence: 99%

Anti-proliferative and pro-apoptotic activity of glycosidic derivatives of lawsone in melanoma cancer cell

et al. 2021

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Background Melanoma is a malignant cancer that affects melanocytes and is considered the most aggressive skin-type cancer. The prevalence for melanoma cancer for the last five year is about one million cases. The impact caused of this and other types of cancer, revel the importance of research into potential active compounds. The natural products are an important source of compounds with biological activity and research with natural products may enable the discovery of compounds with potential activity in tumor cells. Methods The Sulforhodamine B was used to determine cell density after treatment with lawsone derivatives. Apoptosis and necrosis were analyzed by flow cytometer. Morphological changes were observed by fluorescence using the Phalloidin/FITC and DAPI stains. The clonogenic and wound healing assays were used to analyze reduction of colonies formation and migratory capacity of melanoma cells, respectability. Results In pharmacological screening, seven compounds derived from lawsone were considered to have high cytotoxic activity (GI > 75%). Three compounds were selected to assess the inhibitory concentration for 50% of cells (IC50), and the compound 9, that has IC50 5.3 μM in melanoma cells, was selected for further analyses in this cell line. The clonogenic assay showed that the compound is capable of reducing the formation of melanoma colonies at 10.6 μM concentration. The compound induced apoptotic morphological changes in melanoma cells and increased by 50% the cells dying from apoptosis. Also, this compound reduced the migratory capacity of melanoma cells. Conclusions The results of this study showed that the evaluated lawsone derivatives have potential activity on tumor cells. The compound 9 is capable of inducing cell death by apoptosis in melanoma cells (B16F10).

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Section: Methodsmentioning

confidence: 99%

Anti-proliferative and pro-apoptotic activity of glycosidic derivatives of lawsone in melanoma cancer cell

et al. 2021

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Crystal structure of 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione

Abstract: The naphthoquinone unit in 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione is essentially planar and the linear propargyl group is nearly perpendicular to the naphthalene ring system. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds form an infinite tape structure.

Cited by 1 publication

References 14 publications

Anti-proliferative and pro-apoptotic activity of glycosidic derivatives of lawsone in melanoma cancer cell

Anti-proliferative and pro-apoptotic activity of glycosidic derivatives of lawsone in melanoma cancer cell

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Crystal structure of 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione

Abstract: The naphtho­quinone unit in 2-hy­droxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione is essentially planar and the linear propargyl group is nearly perpendicular to the naphthalene ring system. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds form an infinite tape structure.

Cited by 1 publication

References 14 publications

Anti-proliferative and pro-apoptotic activity of glycosidic derivatives of lawsone in melanoma cancer cell

Anti-proliferative and pro-apoptotic activity of glycosidic derivatives of lawsone in melanoma cancer cell

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Abstract: The naphthoquinone unit in 2-hydroxy-3-(prop-2-yn-1-yl)naphthalene-1,4-dione is essentially planar and the linear propargyl group is nearly perpendicular to the naphthalene ring system. In the crystal, O—H⋯O and C—H⋯O hydrogen bonds form an infinite tape structure.