title: [Reactivity of oligonucleotide derivatives, containing methylphosphonate groups. VI. Increase in the effectiveness of directed action of alkylating derivatives of oligonucleotide methylphosphonate analogs on nucleic acids in the presence of effectors--3',5'-bis-N-(2-hydroxyethyl)-phenazine derivatives of oligonucleotides].
abstract: Effectors for increasing the efficiency of DNA modification with the alkylating methylphosphonate analogues of oligodeoxyribonucleotides (MFAO) were suggested. Oligodeoxyribonucleotide d(pC5A8ACAATG) used as a target DNA treated with alkylating derivatives of octathymidylate having alternating methylphosphonate and phosphodiester internucleotide bonds (both Rp- and Sp-individual diastereoisomers of MFAO were used) and bearing alkylating 4-(N-methyl-N-2-chloroethylamino)benzyl phosphoramide residue at the 3'-end. The reactions were carried out in the presence of an effector, hexadeoxyribonucleotide derivative PhnNH(CH2)2NHpCATTGTpNH(CH2)2NHPhn bearing two N-(2-hydroxyethyl)phenazinium (Phn) residues at the 3'- and 5'-ends and being complementary to the part of the target DNA neighbouring with octaadenylate. It was shown that Tm of the duplex formed by the target DNA, octathymidylate and effector is by 7-13 degrees C higher than in the absence of the effector, thus considerably increasing the efficiency of the intracomplex alkylation of the target (e.g., at 40 degrees C, the increase for the reagent based on the Rp-isomer is sixfold). Specificity of the target DNA modification by the MFAO alkylating derivatives in the presence of effector is same as with reagents based on oligodeoxyribonucleotides with natural internucleotide bonds.
authors.forename: N V
authors.initials: NV
authors.lastname: Amirkhanov
authors.forename: V F
authors.initials: VF
authors.lastname: Zarytova
authors.forename: A S
authors.initials: AS
authors.lastname: Levina
mesh_terms: D000477:Alkylating Agents; D001483:Base Sequence; D004247:DNA / Q000737:chemistry* / Q000187:drug effects; D004591:Electrophoresis, Polyacrylamide Gel; D008969:Molecular Sequence Data; D009841:Oligonucleotides / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010619:Phenazines / Q000737:chemistry*; D013696:Temperature
chemical_list: D000477:Alkylating Agents; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D010619:Phenazines; C032627:methylphosphonic acid; D004247:DNA
vernacular_title: Reaktsionnosposobnye proizvodnye oligonukleotidov, soderzhashchikh metilfosfonatnye gruppy. VI. Povyshenie éffektivnosti napravlennogo vozdeĭstviia na nukleinovye kisloty alkiliruiushchikh proizvodnykh metilfosfonatnykh analogov oligonukleotidov v prisutstvii éffektorov--3'5'-bis-N-(2-gidroksiétil) fenazinievykh proizvodnykh oligonukleotidov.