Abstract
The reaction between trans-diamminedichloroplatinum(II) and single-stranded oligonucleotides containing the sequence d(GXG) (X being an adenine, cytosine or thymine residue) yields trans-[Pt(NH3)2[(GXG)-GN7,GN7]] intrastrand cross-links. These cross-links do not prevent the pairing of the platinated oligonucleotides with their complementary strands but they decrease the thermal stability of the duplexes. The thermal stability is not much affected by the chemical nature of the X residue and its complementary base. By gel electrophoresis, it is shown that the trans- [Pt(NH3)2[d(GTG)-GN7,GN7]] cross-link bends the DNA double helix (26 degrees) and unwinds it (45 degrees). The pairing of the platinated oligonucleotides with their complementary strands promotes the rearrangement of the 1,3-intrastrand cross-links into interstrand cross-links. At a given temperature, the nature of the X residue, its complementary base and of the base pairs adjacent to the adducts do not dramatically affect the rate of the reaction. To know whether trans-[Pt(NH3)2[d(GXG)-GN7,GN7]] cross-links do not rearrange in some sequences, the location of these adducts was searched in double-stranded DNA after reaction with trans-diamminedichloroplatinum(II) by means of the 3'-5' exonuclease activity of T4 DNA polymerase. At low level of platination, trans-[Pt(NH3)2[d(GXG)-GN7,GN7]] cross-links were not detected. Monofunctional adducts and interstrand cross-links were mainly formed. These results are discussed in relation with the clinical inefficiency of trans-diamminedichloroplatinum(II).
MeSH Terms
Base Sequence
Cisplatin/chemistry
Cross-Linking Reagents
DNA/chemistry
DNA, Single-Stranded/chemistry
DNA-Directed DNA Polymerase
Drug Stability
Hot Temperature
Molecular Sequence Data
Nucleic Acid Conformation
Oligonucleotides/chemistry
Stereoisomerism
Viral Proteins/metabolism
Chemicals
Cross-Linking Reagents
DNA, Single-Stranded
Oligonucleotides
Viral Proteins
gene 43 protein, Enterobacteria phage T4
transplatin
DNA
DNA-Directed DNA Polymerase
Cisplatin
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Boudvillain M
Centre de Biophysique Moleculaire, CNRS, Orleans, France.
Dalbiès R
Aussourd C
Leng M
References (26)
26 references, click to expand
-
Linkage isomerization reaction of intrastrand cross-links in trans-diamminedichloroplatinum(II)-modified single-stranded oligonucleotides.
Nucleic Acids Res. 1995 Mar 25;23(6):949-53
PMID: 7731808
-
Rapid gene-specific repair of cisplatin lesions at the human DUG/DHFR locus comprising the divergent upstream gene and dihydrofolate reductase gene during early G1 phase of the cell cycle assayed by using the exonucleolytic activity of T4 DNA polymerase.
Proc Natl Acad Sci U S A. 1994 Nov 8;91(23):10977-81
PMID: 7971995
-
Sequence-dependent termination of in vitro DNA synthesis by cis- and trans-diamminedichloroplatinum (II).
Proc Natl Acad Sci U S A. 1985 Jul;82(14):4616-9
PMID: 3895221
-
DNA bending at adenine . thymine tracts.
Nature. 1986 Apr 10-16;320(6062):501-6
PMID: 3960133
-
Characterization of the ternary complexes formed in the reaction of cis-diamminedichloroplatinum (II), ethidium bromide and nucleic acids.
Nucleic Acids Res. 1987 Feb 25;15(4):1779-97
PMID: 3822839
-
Interaction of trans-diamminedichloroplatinum(II) with DNA: formation of monofunctional adducts and their reaction with glutathione.
Biochemistry. 1987 Jun 16;26(12):3303-7
PMID: 3651385
-
The formation, isolation and characterization of DNA adducts produced by anticancer platinum complexes.
Pharmacol Ther. 1987;34(2):155-66
PMID: 3317449
-
Calibration of DNA curvature and a unified description of sequence-directed bending.
Proc Natl Acad Sci U S A. 1988 Mar;85(6):1763-7
PMID: 3162306
-
The major adduct of the antitumor drug cis-diamminedichloroplatinum(II) with DNA bends the duplex by approximately equal to 40 degrees toward the major groove.
Proc Natl Acad Sci U S A. 1988 Jun;85(12):4158-61
PMID: 3380785
-
Characterization of bifunctional adducts produced in DNA by trans-diamminedichloroplatinum(II).
Chem Biol Interact. 1988;67(1-2):71-80
PMID: 3262435
-
Identification and characterization of a novel linkage isomerization in the reaction of trans-diamminedichloroplatinum(II) with 5'-d(TCTACGCGTTCT).
Biochemistry. 1990 Feb 27;29(8):2102-10
PMID: 2328242
-
Synthesis and characterization of trans-[Pt(NH3)2Cl2] adducts of d(CCTCGAGTCTCC).d(GGAGACTCGAGG).
Biochemistry. 1990 Jan 23;29(3):811-23
PMID: 2159792
-
Determination of the extent of DNA bending by an adenine-thymine tract.
Biochemistry. 1990 May 1;29(17):4227-34
PMID: 2361140
-
Distortions induced in double-stranded oligonucleotides by the binding of cis- or trans-diammine-dichloroplatinum(II) to the d(GTG) sequence.
Nucleic Acids Res. 1990 Aug 11;18(15):4395-400
PMID: 2388824
-
Bending studies of DNA site-specifically modified by cisplatin, trans-diamminedichloroplatinum(II) and cis-[Pt(NH3)2(N3-cytosine)Cl]+.
Biophys Chem. 1990 Apr;35(2-3):179-88
PMID: 2397272
-
Interstrand cross-links are preferentially formed at the d(GC) sites in the reaction between cis-diamminedichloroplatinum (II) and DNA.
Proc Natl Acad Sci U S A. 1991 Mar 1;88(5):1982-5
PMID: 2000402
-
DNA unwinding produced by site-specific intrastrand cross-links of the antitumor drug cis-diamminedichloroplatinum(II).
Biochemistry. 1991 Aug 13;30(32):8026-35
PMID: 1868076
-
Phosphorodithioate DNA as a potential therapeutic drug.
Science. 1993 Mar 12;259(5101):1564-70
PMID: 7681216
-
Detection of minor adducts in cisplatin-modified DNA by transcription footprinting.
FEBS Lett. 1993 May 24;323(1-2):55-8
PMID: 8495748
-
DNA interstrand cross-links of trans-diamminedichloroplatinum(II) are preferentially formed between guanine and complementary cytosine residues.
Proc Natl Acad Sci U S A. 1993 Jun 1;90(11):5345-9
PMID: 8506383
-
DNA conformational change produced by the site-specific interstrand cross-link of trans-diamminedichloroplatinum(II).
Biochemistry. 1993 Nov 2;32(43):11676-81
PMID: 8218235
-
Instability of the monofunctional adducts in cis-[Pt(NH3)2(N7-N-methyl-2-diazapyrenium)Cl](2+)-modified DNA: rates of cross-linking reactions in cis-platinum-modified DNA.
Nucleic Acids Res. 1993 Dec 25;21(25):5846-51
PMID: 8290343
-
Sequence specificity of DNA-DNA interstrand cross-link formation by cisplatin and dinuclear platinum complexes.
Biochemistry. 1994 May 10;33(18):5404-10
PMID: 8180163
-
Gradual and oriented B-Z transition in 5'-untranscribed region of mouse ribosomal DNA.
J Biol Chem. 1994 Jul 29;269(30):19238-44
PMID: 8034685
-
DNA double helix promotes a linkage isomerization reaction in trans-diamminedichloroplatinum(II)-modified DNA.
Proc Natl Acad Sci U S A. 1994 Aug 16;91(17):8147-51
PMID: 8058771
-
A new method for sequencing DNA.
Proc Natl Acad Sci U S A. 1977 Feb;74(2):560-4
PMID: 265521