Cytotoxicity of new n-butylamino and sulfur-containing derivatives of polyfluorinated 1,4-naphthoquinone.
Four new n-butylamino and two sulfur-containing derivatives of polyfluoro-1,4-naphthoquinone were synthesized and their mutagenic and antioxidant properties in Salmonella cells, as well as the cytotoxicity in human myeloma (RPMI 8226), human mammary adenocarcinoma (MCF-7), mouse fibroblasts (LMTK) and primary mouse fibroblast cells (PMF) were studied. 2-n-Butylamino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (1) showed efficient inhibition of the growth of the tumor cells. 2,8-Di-(n-butyl-amino)-3,5,6,7-tetrafluoro-1,4-naphthoquinone (2) had significantly less growth-inhibiting properties, while 2,6-di-(n-butylamino)-3,5,7,8-tetrafluoro-1,4-naphthoquinone (3) and 2,6,8-tri-(n-butylamino)-3,5,7-tetrafluoro-1,4-naphthoquinone (4), demonstrated very low cytotoxicity. Compounds 1 and 2 were remarkably less cytotoxic while compound 3 and 4 were not cytotoxic toward LMTK and PMF cells as compared with tumor human cell lines. Cytotoxicity of 2-(2'-methylthioethyl)amino-3,5,6,7,8-pentafluoro-1,4-naphthoquinone (5) and (2,2'-dithiodi-2)-3,5,6,7,8-pentafluoro-1,4-naphthoquinone-2-ylamino)ethan (6) toward mammalian cells was compared with that for compounds 1 and 2.
Zakharova
Ol'ga A
OA
Institute of Biological Chemistry and Fundamental Medicine, Siberian Division of Russian Academy of Sciences, 8 Lavrentiev Ave., 630090 Novosibirsk, Russia.
Goryunov
Leonid I
LI
Troshkova
Nadezhda M
NM
Ovchinnikova
Ludmila P
LP
Shteingarts
Vitalij D
VD
Nevinsky
Georgy A
GA
D000588:Amines / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects / Q000235:genetics; D045744:Cell Line, Tumor; D005461:Fluorine / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D051379:Mice; D016296:Mutagenesis / Q000187:drug effects; D009285:Naphthoquinones / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D013455:Sulfur / Q000737:chemistry*
D000588:Amines; D000970:Antineoplastic Agents; D000975:Antioxidants; D009285:Naphthoquinones; D005461:Fluorine; D013455:Sulfur; C035342:1,4-naphthoquinone