2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ethers: Their Cytotoxic Activity

Ishikawa, Tsutomu; Saito, Tatsuru; Kurosawa, Ayako; Watanabe, Tetsu; Maruyama, Sakiko; Ichikawa, Y.; R, Yamada; Okuzawa, Hiroko; Sato, Hiromi; Ueno, Koichi

doi:10.1248/cpb.59.472

Cited by 7 publications

(6 citation statements)

References 11 publications

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“…201 The active compounds were then further screened against a panel of eight cancer cell-lines comprised of ovarian cancer (HeLa), renal cancer (Caki-1and 786-O), lung cancer (A549), breast cancer (MCF-7) and mesothelioma cancer (H28, H2052, and MSTO-211H). 201 The active compounds were then further screened against a panel of eight cancer cell-lines comprised of ovarian cancer (HeLa), renal cancer (Caki-1and 786-O), lung cancer (A549), breast cancer (MCF-7) and mesothelioma cancer (H28, H2052, and MSTO-211H).…”

Section: -Aryl-14-naphthoquinone-1-oxime Methyl Ethersmentioning

confidence: 99%

Understanding cancer and the anticancer activities of naphthoquinones – a review

2015

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The non-communicable disease, cancer, is one of the major causes of death across the world and is forecast to increase by 75% to reach close to 25 million cases over the next two decades. Radiotherapy and surgical approaches have been unsuccessful in controlling the incidence of most cancers. The development of chemotherapeutic strategies involving novel small molecule antitumour agents has therefore been the focus area of cancer chemotherapy for several decades as another strategy to combat and control the incidence of cancer. Many natural products as well as several synthetic drugs have a naphthoquinone chromophore. The anticancer activities of naphthoquinones have been the focus of much research to discover novel anticancer agents. The naturally occurring 1,2-naphthoquinone-based compound, ß-Lapachone (ARQ 761), is currently being assessed for its anti-tumour activity against advanced solid tumours. This review describes the most recent applications of naphthoquinones and their derivatives in cancer drug discovery. The biology relevant to the design of novel naphthoquinone anticancer agents is also discussed. Furthermore, the discussion of the biology will contribute to understanding cancer as well as the applications of naphthoquinones as anticancer agents.

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Section: -Aryl-14-naphthoquinone-1-oxime Methyl Ethersmentioning

confidence: 99%

Understanding cancer and the anticancer activities of naphthoquinones – a review

2015

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“…Macarpine and QO-1 were chemically synthesized by Ishikawa et al (1,2). Macarpine, QO-1, paclitaxel (TAX), vinblastine (VBL), and vinorelbine (VNR) (Wako Pure Chemical Industry, Osaka) were dissolved in and diluted with dimethyl sulfoxide (DMSO) and stored at −20°C at a concentration of 5 mM.…”

Section: Reagentsmentioning

confidence: 99%

“…1A. It has been suggested in a preliminary experiment on the structureactivity relationship (SAR) that the 6,7-methylenedioxy-1,4-naphthoquinone-1-oxime methyl ether skeleton, a common core structure in the 2-aryl-1,4-naphthoquinone-1-oxime methyl ether derivatives, could play an important role for the activity of these compounds (2,3).…”

Section: Introductionmentioning

confidence: 99%

New 2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ether Compound Induces Microtubule Depolymerization and Subsequent Apoptosis

Sato

Yanagihara

et al. 2012

J Pharmacol Sci

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Abstract. In this study, we describe the antitumor activity of QO-1, one of the new 2-aryl-1,4-naphthoquinone-1-oxime methyl ether derivatives. QO-1 is a derivative of macarpine, a natural occurring product from Rutaceae plant. It could potently inhibit cell growth when tested on 19 cancer cell lines. To investigate its mechanism, two cell lines (HeLa and MCF-7) sensitive to QO-1 were selected. Based on flow cytometry, it was found to induce G 2 /M-phase arrest. Moreover, it could cause microtubule depolymerization both in vitro and in vivo. On the other hand, QO-1 activated spindle assembly checkpoint (SAC) proteins. Expression of Bub1, one of the SAC, was gradually increased, reaching a peak after 16 -20 h, and then gradually decreased. Instead, QO-1 increased the sub-G 1 population, which suggested a cell death population. Actually, expression of Bcl-2 family proteins and activation of caspase-3/7 were evidences of apoptosis. Consistent with these results, cells with DNA fragmentation and multinucleated cells were increased timedependently after QO-1 exposure. In conclusion, QO-1 has promising antitumor effects via microtubule depolymerization.

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“…The derivatization of naphthoquinone has been the subject of great interest among researchers in the biomedical field, since a plethora of synthetic and natural naphthoquinones have already been reported as potent anticancer agents. These quinones include aminonaphthoquinones, sulfonamide derivatives of naphthoquinones, heterocycle fused naphthoquninones, quinone monoxime derivatives, amide, ester and triazole functionalized, and glycosylated naphthoquinones…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Quinone‐Based N‐Sulfonyl‐1,2,3‐triazoles: Chemical Reactivity of Rh(II) Azavinyl Carbenes and Antitumor Activity

et al. 2017

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Quinone‐based N‐sulfonyl‐1,2,3‐triazoles were synthesized by click chemistry and subsequently evaluated against eight types of cancer cell lines. Some of the compounds exhibited potent cytotoxicity with IC50 values < 1.0 μM. Also, the cytotoxic potential of the quinones was evaluated against peripheral blood mononuclear (PBMC) and V79 cells. Additionally, the chemical reactivity of Rh(II) aza‐vinyl carbenes generated in situ from these triazoles was studied. These compounds could provide promising new lead derivatives for more potent anticancer drug development.

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2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ethers: Their Cytotoxic Activity

Cited by 7 publications

References 11 publications

Understanding cancer and the anticancer activities of naphthoquinones – a review

Understanding cancer and the anticancer activities of naphthoquinones – a review

New 2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ether Compound Induces Microtubule Depolymerization and Subsequent Apoptosis

Synthesis of Quinone‐Based N‐Sulfonyl‐1,2,3‐triazoles: Chemical Reactivity of Rh(II) Azavinyl Carbenes and Antitumor Activity

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