Cytotoxicity of new polyfluorinated 1,4-naphtoquinones with diverse substituents in the quinone moiety

Cytotoxicity of new polyfluorinated 1,4-naphtoquinones with diverse substituents in the quinone moiety Full article

Journal

Bioorganic and Medicinal Chemistry
ISSN: 0968-0896 , E-ISSN: 1464-3391

Output data

Year: 2011, Volume: 19, Number: 1, Pages: 256-260 Pages count : DOI: 10.1016/j.bmc.2010.11.027

Tags

Fluorinated derivatives of 1,4-naphthoquinones; Antitumor

Authors

Zakharova Ol'ga D. ¹ , Ovchinnikova Ludmila P. ² , Goryunov Leonid I. ³ , Troshkova Nadezhda M. ³ , Shteingarts Vitalij D. ³ , Nevinsky Georgy A. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Inst Chem Biol & Fundamental Med, Siberian Div, Novosibirsk 630090, Russia
2	(Данные Web of science) Russian Acad Sci, Inst Cytol & Genet, Siberian Div, Novosibirsk 630090, Russia
3	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

Fluorinated derivatives of 1,4-naphthoquinones are highly potent inhibitors of Cdc25A and Cdc25B phosphatases and growth of tumor cells. Eight new derivatives of polyfluoro-1,4-naphthoquinone were synthesized and their cytotoxicity in human myeloma, human mammary adenocarcinoma, mouse fibroblasts and primary mouse fibroblast cells as well as their mutagenic and antioxidant properties in a Salmonella tester strain were studied. The efficiency of suppressing the growth of two lines of tumor cells decreased in the order: 2-(2-hydroxy-ethylamino)-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (1), 2,3-dimethoxy5,6,7,8-tetrafluoro-1,4-naphthoquinone (2), 2-[2- hydroxyethyl(methyl) amino]-3,5,6,7,8-pentafluoro-1, 4-naphthoquinone (3), 2-morpholino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (4), 2-[bis-(2-hydroxyethyl)amino]-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (5), 2-[(2- hydroxy)ethylsulfanyl)]-5,6,7,8-tetrafluoro-1,4-naphthoquinone (6), 2-methoxy-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (7), and 1,4-dioxo-3-(1-pyridinio)-1,4-dihydro-5,6,7,8-tetrafluoronaphthalene-2-olate (8). Taking into account these data together with the better cytotoxic effect against cancer cells as compared with normal mammalian cells, protecting of bacterial cells from spontaneous and H2O2-dependent mutagenesis, and lower general toxicity of the compounds towards different cells, one can propose that compounds 3-5 may be considered as useful potential inhibitors of growth of tumor cells. (C) 2010 Elsevier Ltd. All rights reserved.

Zakharova O.D. , Ovchinnikova L.P. , Goryunov L.I. , Troshkova N.M. , Shteingarts V.D. , Nevinsky G.A.
Cytotoxicity of new polyfluorinated 1,4-naphtoquinones with diverse substituents in the quinone moiety
Bioorganic and Medicinal Chemistry. 2011. V.19. N1. P.256-260. DOI: 10.1016/j.bmc.2010.11.027 WOS Scopus РИНЦ OpenAlex

Published print:

Jan 1, 2011

Web of science:	WOS:000285724800025
Scopus:	2-s2.0-78650727345
Elibrary:	16647169
OpenAlex:	W2070017200

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Scopus	15
Elibrary	14
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