title: [Synthesis, properties and interaction with eukaryotic cells of alkylating derivatives of oligodeoxyribonucleotides containing cholesterol or phenazinium residue covalently bound to the 3'-terminus].
abstract: Radioactive alkylating 5'-[32P]-[4-(N-2-chlorethyl)N-methylaminobenzyl]-5'-phospham ide decadeoxyribothymidilate derivatives containing either free hydroxyl group (reagent I), hydrophobic cholesterol residue (reagent II) or polyaromatic phenazinium residue (reagent III) at 3'-termini were synthesized. The products were purified by HPLC and used for oligonucleotide-directed alkylating of DNA in isolated rat liver nuclei, Krebs-2 ascite carcinoma cells and L-929 murine fibroblasts. The uptake of reagent II by the cells was two orders of magnitude higher than that of reagent I and III. Intracellular alkylation of DNA by reagent II both in isolated nuclei and in living cells was about one order of magnitude higher than in the case of reagent I. The presence of phenazinium at 3'-termini of the reagent III leads to a sufficient increase of the alkylation extent compared to reagent I despite a quite low extent of its uptake by the cells.
authors.forename: A S
authors.initials: AS
authors.lastname: Butorin
authors.forename: V V
authors.initials: VV
authors.lastname: Vlasov
authors.forename: L V
authors.initials: LV
authors.lastname: Gus'kova
authors.forename: V F
authors.initials: VF
authors.lastname: Zarytova
authors.forename: E M
authors.initials: EM
authors.lastname: Ivanova
authors.forename: N D
authors.initials: ND
authors.lastname: Kobets
authors.forename: A S
authors.initials: AS
authors.lastname: Raĭt
authors.forename: L V
authors.initials: LV
authors.lastname: Iurchenko
mesh_terms: D000477:Alkylating Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D000478:Alkylation; D000818:Animals; D002287:Carcinoma, Krebs 2 / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D002784:Cholesterol; D002843:Chromatin / Q000187:drug effects / Q000378:metabolism; D004247:DNA / Q000187:drug effects* / Q000378:metabolism; D004273:DNA, Neoplasm / Q000187:drug effects / Q000378:metabolism; D007202:Indicators and Reagents; D007739:L Cells; D051379:Mice; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D010619:Phenazines; D051381:Rats; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000477:Alkylating Agents; D002843:Chromatin; D004273:DNA, Neoplasm; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D010619:Phenazines; D004247:DNA; D002784:Cholesterol
vernacular_title: Sintez, svoĭstva i vzaimodeĭstvie s éukarioticheskimi kletkami alkiliruiushchikh proizvodnykh oligodezoksiribonukleotidov, soderzhashchikh kovalentno prisoedinennyĭ k 3'-kontsu ostatok kholesterina ili fenaziniia.