caa a22 4500 465789390 CHVBK 20180323112019.0 cr unu---uuuuu 170327e19900201xx s 000 0 eng 10.1007/BF00216918 doi (NATIONALLICENCE)springer-10.1007/BF00216918 Fluorinated anthracyclines: Synthesis and biological activity [Elektronische Daten] [Ken Tonkin, Robert Brownlee, Franco Zunino, Don Phillips] A number of fluorine containing derivatives of daunomycin and Adriamycin have been synthesised with a fluorine substituent located on the C-9 side chain. They included the p-trifluoromethyl-(4) and p-fluorobenzoate (3) esters of Adriamycin and the trifluoro-ethyl-hydrazones of Adriamycin (2) and daunomycin (1). The less polar derivatives (esters 3 and 4) appear to enter HeLa cells more readily than the polar derivatives (hydrazones 1 and 2) as indicated by the rates and extent of cellular uptake and the uptake was by facilitated diffusion. All four fluorinated derivatives were less active than their parent anthracyclines, but the difference was less pronounced when considering specific potency. The fluorinated derivatives (1-4) behaved sufficiently similar to daunomycin and Adriamycin to enable their use as fluorine probes in 19F NMR physicochemical and cellular studies of anthracyclines. Kluwer Academic Publishers, 1990 fluorinated anthracyclines nationallicence HPLC nationallicence cell accumulation nationallicence cytotoxicity nationallicence NMR nationallicence Tonkin Ken Department of Biochemistry, La Trobe University, 3083, Bundoora, Victoria, Australia aut Brownlee Robert Department of Chemistry, La Trobe University, 3083, Bundoora, Victoria, Australia aut Zunino Franco Division of Experimental Oncology B, National Cancer Institute, Milan, Italy aut Phillips Don Department of Biochemistry, La Trobe University, 3083, Bundoora, Victoria, Australia aut Investigational New Drugs Kluwer Academic Publishers 8/1(1990-02-01), 1-6 0167-6997 8:1<1 1990 8 10637 https://doi.org/10.1007/BF00216918 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00216918 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Tonkin Ken Department of Biochemistry, La Trobe University, 3083, Bundoora, Victoria, Australia aut NATIONALLICENCE 700 1- Brownlee Robert Department of Chemistry, La Trobe University, 3083, Bundoora, Victoria, Australia aut NATIONALLICENCE 700 1- Zunino Franco Division of Experimental Oncology B, National Cancer Institute, Milan, Italy aut NATIONALLICENCE 700 1- Phillips Don Department of Biochemistry, La Trobe University, 3083, Bundoora, Victoria, Australia aut NATIONALLICENCE 773 0- Investigational New Drugs Kluwer Academic Publishers 8/1(1990-02-01), 1-6 0167-6997 8:1<1 1990 8 10637 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer