Nucleic Acids Research, 1995, Vol. 23, No. 6 949-953
© 1995
CHEMISTRY |
Linkage isomerization reaction of intrastrand cross-links in trans-diamminedichloroplatinum(II)-modified single-stranded oligonucleotides
Centre de Biophysique Moléculaire, CNRS, Rue Charles Sadron, 45071 Orleans Cedex 2, France
*To whom correspondence should be addressed
Received December 9, 1994. Revised February 2, 1995. Accepted February 2, 1995.
The stability of trans-{Pt(NH3)2[d(CGAG)-N7-G,N7-G]} adducts, resulting from cross-links between two guanine residues at d(CGAG) sites within single-stranded oligonucleotides by trans-diamminedichloro-platinum(II), has been studied under various conditions of temperature, salt and pH. The trans-{Pt(NH3)2[d(CGAG)-N7-G,N7-G]} cross-links rearrange into trans-{Pt(NH3)2[d(CGAG)-N3-C,N7-G]} cross-links. The rate of rearrangement is independent of pH, in the range 5–9, and of the nature and concentration of the salt (NaCl or NaClO4) In the range 10–400 mM. The reaction rate depends upon temperature, the t
values for the disappearance of the (G,G) Intrastrand crosslink ranging from 120 h at 30°C. to 70 min at 80°C. The linkage Isomerization reaction occurs In oligonucleotides as short as the platinated tetramer d(CGAG). Replacement of the intervening residue A by T has no major effect on the reaction. The C residue adjacent to the adduct on the 5' side plays a key-role in the reaction; its replacement by a G, A or T residue prevents the reaction occuring. No rearrangement was observed with the C residue adjacent to the adduct on the 3' side. It is proposed that the linkage isomerization reaction results from a direct attack of the base residue on the platinum(II) square complex.
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