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Lapachone AND dunnione

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https://www.readbyqxmd.com/read/26088596/synthesis-characterization-and-antileukemic-properties-of-naphthoquinone-derivatives-of-lawsone
#1
Ryuta Inagaki, Masayuki Ninomiya, Kaori Tanaka, Mamoru Koketsu
Naphthoquinones are considered privileged structures for anticancer drug molecules. The Heck reaction of 2-hydroxy-1,4-naphthoquinone (lawsone) with 1-bromo-3-methyl-2-butene offered easy access to lapachol. Several naturally occurring linear and angular heterocyclic quinoids (α-lapachone, β-lapachone, dunnione, and related analogues) were prepared from lapachol. Furthermore, we demonstrated that the synthetic naphthoquinones inhibit cell proliferation in human leukemia HL-60 cells. In particular, angular-type derivatives were found to possess moderate cytotoxicity and to elevate the levels of intracellular glutathione disulfide (GSSG)...
August 2015: ChemMedChem
https://www.readbyqxmd.com/read/10203579/bcl-2-protects-against-beta-lapachone-mediated-caspase-3-activation-and-apoptosis-in-human-myeloid-leukemia-hl-60-cells
#2
S M Planchon, S M Wuerzberger-Davis, J J Pink, K A Robertson, W G Bornmann, D A Boothman
We previously demonstrated that beta-lapachone (beta-lap) killed cancer cells solely by apoptosis. Beta-Lap induced apoptosis in HL-60 cells in a dose-dependent manner as measured by flow cytometry and DNA ladder formation. Cell cycle changes, such as accumulations in S and G2-phases, were not observed. Apoptosis was accompanied by activation of caspase 3 and concomitant cleavage of poly(ADP-ribose) polymerase (PARP) to an 89 kDa polypeptide. PARP cleavage was blocked by zDEVD-fmk or zVAD-fmk, caspase-specific cleavage site inhibitors...
May 1999: Oncology Reports
https://www.readbyqxmd.com/read/9660542/effects-of-1-2-naphthoquinones-on-human-tumor-cell-growth-and-lack-of-cross-resistance-with-other-anticancer-agents
#3
M E Dolan, B Frydman, C B Thompson, A M Diamond, B J Garbiras, A R Safa, W T Beck, L J Marton
The sensitivity of human tumor and rat prostate tumor cells to a series of naphthoquinones, including tricyclic compounds of the beta-lapachone and dunnione families as well as 4-alkoxy-1,2-naphthoquinones, was evaluated. To better understand the mechanism of cytotoxicity of 1,2-naphthoquinones, the roles of various resistance mechanisms including P-glycoprotein, multidrug resistant associated protein, glutathione (GSH) and related enzymes, altered topoisomerase activity, and overexpression of genes that control apoptosis (bcl-2 and bc-xL) were studied...
June 1998: Anti-cancer Drugs
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