[Porphyrin derivatives of oligonucleotides. I. Synthesis of oligonucleotide derivatives bearing 2,4-di(alpha-(2-hydroxyethoxy)ethyl)- deuteroporphyrin IX or a metal complex of it and study of the oxidative modification of DNA by these derivatives].
A method for coupling 2,4-di[alpha-(2-hydroxyethoxy)ethyl] deuteroporphyrin dimethyl ether (IX), DDPOH and its complexes with metals to the 5'- or 3'-end of oligonucleotides was elaborated. In the presence of an oxidizing agent (H2O2), Fe(III)DDP-derivatives of oligonucleotides modified single-stranded DNA. The reaction was strictly site-specific and occurred at two neighbouring guanosine residues. A few types of modification were observed: cross-linking, modification leading to DNA cleavage upon piperidine treatment, and direct chain scission. The total modification yield reached 90%. Covalent attachment of Fe(III)DDP-group to oligonucleotides increased the efficiency of their uptake and the melting temperature of their complementary complexes.
E I
EI
Frolova
E M
EM
Ivanova
N I
NI
Komarova
A S
AS
Raĭm
V V
VV
Vlasov
G V
GV
Ponomarev
G V
GV
Kirillova
D001483:Base Sequence; D003432:Cross-Linking Reagents; D004247:DNA / Q000737:chemistry*; D003905:Deuteroporphyrins / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D008969:Molecular Sequence Data; D009841:Oligonucleotides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011166:Porphyrins / Q000737:chemistry*
D003432:Cross-Linking Reagents; D003905:Deuteroporphyrins; D008670:Metals; D009841:Oligonucleotides; D011166:Porphyrins; C081204:2,4-di-(2-hydroxyethoxy)ethyl-deuteroporphyrin IX; D004247:DNA
Porfirinovye proizvodnye oligonukleotidov. I. Sintez proizvodnykh oligonukleotidov nesushchikh 2,4-di(alpha-(2-gidroksiétoksi)étil)- deĭteroporfirin IX ili ego metallokompleksy i issledovanie okislitel'noĭ modifikatsii DKN étimi proizvodnymi.