Complementary addressed reagents carrying EDTA‐Fe(II) groups for directed cleavage of single‐stranded nucleic acids

Boutorin, A.S.; Vlassov, V. V.; Kazakov, S. A.; Kutiavin, I. V.; Podyminogin, Mikhail A.

doi:10.1016/0014-5793(84)80869-8

Cited by 73 publications

(21 citation statements)

References 10 publications

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“…27 for review). It is also possible to induce strand breaks in the target nucleic acid by covalent linkage of metal complexes that generate hydroxyl radicals (27)(28)(29)(30)(31)(32)(33). Here we describe a photoactive system that can be used to photocrosslink the oligonucleotide to its complementary sequence.…”

Section: Discussionmentioning

confidence: 99%

Sequence-specific binding and photocrosslinking of alpha and beta oligodeoxynucleotides to the major groove of DNA via triple-helix formation.

Praseuth

Perrouault

Doan

et al. 1988

Proc. Natl. Acad. Sci. U.S.A.

217

119

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A photocrosslinking reagent (p-azidophenacyl) was covalently linked to an octathymidylate synthesized with either the natural ((3) anomer of thymidine or the synthetic (a) anomer. The oligothymidylate was further substituted by an acridine derivative to stabilize the hybrid formed with a complementary octadeoxyadenylate sequence via intercalation. A single-stranded 27-mer containing a (dA)8 sequence and a 27-mer duplex containing a (dA-dT)8 sequence were used as targets. Upon UV irradiation, photocrosslinking of the octathymidylate to its target sequence was observed, generating bands that migrated more slowly in denaturing gels. In the 27-mer duplex, both strands were photocrosslinked to the octathymidylate. Upon alkaline treatment of the irradiated samples, cleavage of the 27-mers was observed at specific sites. These reactions were analyzed at different salt concentrations. The location of the cleavage sites allowed us to demonstrate the following. (i) Both a and (3 oligothymidylates can recognize a DNA double helix containing an oligo(dA)-oligo(dT) sequence; the oligothymidylate binds to the major groove of DNA in a parallel orientation with respect to the adenine-containing strand of the DNA double helix. (ii) a oligothymidylates form helices with a complementary singlestranded oligodeoxyadenylate; the two strands have a parallel orientation independently of whether or not an intercalating agent is attached to the oligothymidylate. (iii) At low salt concentration, (3 oligothymidylates form a double helix with an oligodeoxyadenylate in which, as expected, the two strands are antiparallel; at high salt concentration, a triple helix is formed in which the second oligothymidylate is oriented parallel to the adenine-containing strand. These results show that it is possible to recognize an oligopurine-oligopyrimidine sequence in a DNA double helix via local triple-helix formation and to target photochemical reactions to specific sequences in both double-stranded and single-stranded nucleic acids.

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Section: Discussionmentioning

confidence: 99%

Sequence-specific binding and photocrosslinking of alpha and beta oligodeoxynucleotides to the major groove of DNA via triple-helix formation.

Praseuth

Perrouault

Doan

et al. 1988

Proc. Natl. Acad. Sci. U.S.A.

217

119

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“…One approach to overcoming this has been to modify a DNA-recognizing molecule chemically with a reagent capable of chemical cleavage of DNA. The most commonly used reagent for such chemical cleavage is probably the Fe(II)-EDTA system, which has been attached to oligonucleotides (Boutorin et al, 1984;Dreyer & Dervan, 1985), to intercalators (Hertzberg & Dervan, 1984) and to a combination of these binding species (Boidet-Forget et al, 1988). Minorgroove-directed drugs (Taylor et al, 1984) and anti-sense oligodeoxyribonucleoside methanephosphonates (Lin et al, 1989) have joined the catalogue.…”

Section: Introductionmentioning

confidence: 99%

Chemical cleavage of plasmid DNA by glutathione in the presence of Cu(II) ions. The Cu(II)-thiol system for DNA strand scission

Reed

Douglas

1991

Biochemical Journal

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In the presence of Cu(II) ions, supercoiled DNA is cleaved in neutral solution by low concentrations of thiols. Supercoiled plasmid DNA is cleaved first to open circular DNA, which in turn produces linear DNA and eventually fragments. Cleavage is strongly temperature-dependent and is maximal at 0.10-0.25 M-NaCl concentration. In the presence of excess of either component of the Cu(II)-thiol pair, the extent of cleavage depended on the concentration of the limiting partner, and was easily detectable down to micromolar concentrations of limiting GSH. Scavengers of oxygen-derived species (such as hydrogen peroxide, superoxide radical ion and hydroxyl radical) indicated that the hydroxyl radical may be involved in the cleavage mechanism. DNA cleavage leads to some production of 2-thiobarbituric acid-reactive species and some of the cleavage sites, at least, had 5'-hydroxy and/or 3'-hydroxy groups. There was extensive base damage before cleavage. Studies with S1 nuclease indicated no gross sequence preference for Cu(II)-GSH cleavage of pSP64 plasmid DNA. The Cu(II)-thiol system did not appear to target special structural features in the DNA such as Z-DNA inserts, cruciform structures or left-handed (but non-Z) DNA. Cleavage might arise from a reagent generated either by the Cu(II)-thiol combination in free solution or by attack involving Cu(II) ions pre-bound to DNA. The attack of GSH plus Cu(II) ions on DNA may be a potential toxic lesion under physiological conditions unless special protective measures operate efficiently in the cell.

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“…They are capable of producing active oxygen-containing species in a catalytic reaction in the presence of oxidants (6)(7)(8)(9)(10). These groups are bound with oligonucleotides and the reagents obtained can site-specifically modify the DNA-target (11)(12)(13)(14)(15). But no catalytic process of degradation of the nucleic acids with the oligonucleotide derivatives bearing reactive groups including EDTA, 1,10-phenanthroline and porphyrines has been demonstrated yet.…”

Section: Introductionmentioning

confidence: 99%

Catalytic site-specific cleavage of a DNA-target by an oligonucleotide carrying bleomycin A5

Sergeyev¹,

Godovikova²,

Зарытова³

1995

Nucl Acids Res

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Complementary addressed reagents carrying EDTA‐Fe(II) groups for directed cleavage of single‐stranded nucleic acids

Cited by 73 publications

References 10 publications

Sequence-specific binding and photocrosslinking of alpha and beta oligodeoxynucleotides to the major groove of DNA via triple-helix formation.

Sequence-specific binding and photocrosslinking of alpha and beta oligodeoxynucleotides to the major groove of DNA via triple-helix formation.

Chemical cleavage of plasmid DNA by glutathione in the presence of Cu(II) ions. The Cu(II)-thiol system for DNA strand scission

Catalytic site-specific cleavage of a DNA-target by an oligonucleotide carrying bleomycin A5

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