title: [Reactive oligonucleotide derivatives containing methylphosphonate groups. V. Increased effectiveness of complementary addressed modification of target DNA by alkylating derivatives of methylphosphonate analogs of octathymidylate containing N-(2-hydroxyethyl)phenazinium residues].
abstract: Efficiency of the intracomplex alkylation of octadecadeoxyribonucleotide d(pC5A8C5) (target) by Rp- and Sp-individual diastereomers of the methylphosphonate octathymidylate 4-(N-methyl-N-2-chloroethylamino)benzyl phosphoramide (-pNHCH2RCl) derivatives bearing an additional N-(2-hydroxyethyl)phenazinium residue (phn), viz. ClRCH2NHpTp.(TpTp)3TpNH(CH2)2NHPhn (I) and PhnNH(CH2)2NHpTp(TpTp)3TpNHCH2RCl (II) (p = -OP(O) (CH3)O-), has been investigated. Stabilisation of the complementary complex formed by the target oligonucleotide and methylphosphonate oligonucleotide derivatives by the Phn group considerably rose the efficiency of the intracomplex alkylation of the target as compared with alkylation by reagents without Phn. RP-isomeric derivatives of (I) and (II) proved to be the most effective alkylating reagents. Specificity of alkylation of nucleic acid target by reagents (I) and (II) is studied.
authors.forename: N V
authors.initials: NV
authors.lastname: Amirkhanov
authors.forename: V F
authors.initials: VF
authors.lastname: Zarytova
mesh_terms: D000477:Alkylating Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001483:Base Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000187:drug effects*; D004249:DNA Damage; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000494:pharmacology*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D010619:Phenazines / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: D000477:Alkylating Agents; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; D010619:Phenazines; D004247:DNA
vernacular_title: Reaktsionnosposobnye proizvodnye oligonukleotidov, soderzhashchikh metilfosfonatnye gruppy. V. Povyshenie éffektivnosti komplementarno- adresovannoĭ modifikatsii DNK-misheni alkiliruiushchimi proizvodnymi metilfosfonatnykh analogov oktatimidilata, soderzhashchimi ostatki N-(2-gidroksiétil)fenaziniia.