Synthesis of quinoidal molecules: Strategies towards bioactive compounds with an emphasis on lapachones

Castro, Solange L. de; Emery, Flávio da Silva; Júnior, Eufrânio N. da Silva

doi:10.1016/j.ejmech.2013.07.057

Cited by 102 publications

(47 citation statements)

References 119 publications

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“…We discovered a series of lapachones with modified C-rings (Scheme 1a) with potent activity against cancer lineages [27]. Lately, interest in preparing quinone-based triazoles has been stimulated by our discovery of bioactive compounds endowed with unique subunits in their chemical structures [28].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

Cruz

Silvers

Jardim

et al. 2016

European Journal of Medicinal Chemistry

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Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian carcinoma cells). Some compounds showed IC50 values < 0.3 μM. The cytotoxic potential of the quinones evaluated was also assayed using non-tumor cells, exemplified by peripheral blood mononuclear (PBMC), V79 and L929 cells. Mechanistic role for NAD(P)H:Quinone Oxidoreductase 1 (NQO1) was also elucidated. These compounds could provide promising new lead derivatives for more potent anticancer drug development and delivery, and represent one of the most active classes of lapachones reported.

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Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

Cruz

Silvers

Jardim

et al. 2016

European Journal of Medicinal Chemistry

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“…[12] On the basis of our experience in developing phenazinic derivatives, herein we describe the synthesis of a probe for Cd 2+ , the design of which was based on the phenazine fluorophore and N,Nbis(2-picolyl)amine as a coordination site bound by a 1,2,3-triazolyl unity, as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Phenazine‐Based 1,2,3‐Triazole from Naturally Occurring Naphthoquinone Designed as a Probe for Cd²⁺ Ions

et al. 2014

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Simultaneously synthesizing and structuring atomically thick or ultrathin 2D non‐precious metal nanocrystal may offer a new class of materials to replace the state‐of‐art noble‐metal electrocatalysts; however, the synthetic strategy is the bottleneck which should be urgently solved. Here we report the synthesis of an ultrathin nickel nanosheet array (Ni‐NSA) through in situ topotactic reduction from Ni(OH)2 array precursors. The Ni nanosheets showed a single‐crystalline lamellar structure with only ten atomic layers in thickness and an exposed (111) facet. Combined with a superaerophobic (low bubble adhesive) arrayed structure the Ni‐NSAs exhibited a dramatic enhancement on both activity and stability towards the hydrazine‐oxidation reaction (HzOR) relative to platinum. Furthermore, the partial oxidization of Ni‐NSAs in ambient atmosphere resulted in effective water‐splitting electrocatalysts for the hydrogen‐evolution reaction (HER).

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“…The natural compound lapachol is the most plentiful naphthoquinoidal compound isolated from the trees of the family Bignoniaceae and has been extensively studied because of its imperative biological activities, including antitumor effect . β‐Lapachone as the most promising compound of the lapachol group is cytotoxic to a diversity of human cancer cells which are naturally more liable to oxidative damage compared to normal cells . β‐Lapachone has been extensively studied in recent years and is now in phase II clinical trials as a monotherapy or in combination with other antitumor drugs .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel benzo[c]acridine‐diones as potential anticancer agents and tubulin polymerization inhibitors

Behbahani

Tabeshpour

Mirzaei

et al. 2019

Archiv der Pharmazie

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A new series of novel benzo[c]acridine-diones possessing pharmacophoric elements of antitubulins with central dihydropyridine bridge were designed and synthesized as potential anticancer agents and tubulin polymerization inhibitors. The cytotoxic activity of the synthesized compounds was evaluated against eight cancer cell lines including MCF-7, A2780, HeLa, HepG2, DU145, A549, PC3, and LNCAP cancer cells and normal cells (HUVEC) through 3-[4,5-dimethylthiazol-2yl]-2,5-diphenyl tetrazolium bromide (MTT) assay, wherein β-lapachone and combretastatin A-4 were used as positive controls. Some of our compounds (4c and 4g) showed significant cytotoxic activity on cancer cells with IC 50 values in the range of 5.23-24.32 μM. None of the synthesized compounds showed significant cytotoxicity on normal HUVEC cells. Among all investigated derivatives, compound 4g showed promising greater antiproliferative activity against all tested cancer cells with the highest sensitivity observed for the PC3 cell line. Results from the flow cytometry analysis of PC3 and MCF-7 cancer cells treated with 4g showed an induced cell-cycle arrest at G2/M, and therefore induced apoptosis which occurred at low concentration of test compound, whereas annexin V-FITC/propidium iodide staining assay in the aforementioned cancer cell lines treated with 4g showed that 4g can cause necrosis in PC3 and MCF-7 cancer cells at higher concentration. Compound 4g proved to be an inhibitor of tubulin polymerization in a mode similar to that of colchicine and in a dose-dependent manner. Molecular docking studies of 4g into the colchicine-binding site of tubulin exhibited a possible mode of interaction between this compound and tubulin.

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Synthesis of quinoidal molecules: Strategies towards bioactive compounds with an emphasis on lapachones

Cited by 102 publications

References 119 publications

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

Synthesis of a Phenazine‐Based 1,2,3‐Triazole from Naturally Occurring Naphthoquinone Designed as a Probe for Cd²⁺ Ions

Synthesis and biological evaluation of novel benzo[c]acridine‐diones as potential anticancer agents and tubulin polymerization inhibitors

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Synthesis of quinoidal molecules: Strategies towards bioactive compounds with an emphasis on lapachones

Cited by 102 publications

References 119 publications

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

Synthesis and antitumor activity of selenium-containing quinone-based triazoles possessing two redox centres, and their mechanistic insights

Synthesis of a Phenazine‐Based 1,2,3‐Triazole from Naturally Occurring Naphthoquinone Designed as a Probe for Cd2+ Ions

Synthesis and biological evaluation of novel benzo[c]acridine‐diones as potential anticancer agents and tubulin polymerization inhibitors

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Synthesis of a Phenazine‐Based 1,2,3‐Triazole from Naturally Occurring Naphthoquinone Designed as a Probe for Cd²⁺ Ions