Steric control of DNA interstrand cross-link sites of trans platinum complexes: specificity can be dictated by planar nonleaving groups
Language English Country Germany Media print
Document type Comparative Study, Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.
PubMed
10907747
DOI
10.1007/pl00010665
Knihovny.cz E-resources
- MeSH
- DNA Adducts metabolism MeSH
- Quinolines chemistry MeSH
- Cisplatin metabolism MeSH
- Cytosine chemistry MeSH
- DNA Footprinting MeSH
- DNA chemistry MeSH
- Guanine chemistry MeSH
- Nucleic Acid Conformation MeSH
- Ligands MeSH
- Oligonucleotides chemical synthesis chemistry MeSH
- Antineoplastic Agents chemistry MeSH
- Cross-Linking Reagents chemistry MeSH
- Base Sequence MeSH
- Stereoisomerism MeSH
- Thiazoles chemistry MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Research Support, U.S. Gov't, Non-P.H.S. MeSH
- Comparative Study MeSH
- Names of Substances
- DNA Adducts MeSH
- Quinolines MeSH
- Cisplatin MeSH
- Cytosine MeSH
- DNA MeSH
- Guanine MeSH
- Ligands MeSH
- Oligonucleotides MeSH
- Antineoplastic Agents MeSH
- quinoline MeSH Browser
- Cross-Linking Reagents MeSH
- Thiazoles MeSH
Recent findings that novel trans-dichloroplatinum(II) complexes exhibit antitumor activity violate the classical structure-activity relationships of platinum(II) complexes. These novel "nonclassical" trans platinum complexes also comprise those containing planar aromatic amines. Initial studies have shown that these compounds form a considerable amount of DNA interstrand cross-links (up to approximately 30%) with a rate markedly higher than clinically ineffective transplatin. The present work has shown, using Maxam-Gilbert footprinting, that trans-[PtCl2(NH3)(quinoline)] and trans-[PtCl2(NH3)(thiazole)], representatives of the group of new antitumor trans-dichloroplatinum complexes containing planar amines, preferentially form DNA interstrand cross-links between guanine residues at the 5'-GC-3' sites. Thus, DNA interstrand cross-linking by trans-[PtCl2(NH3)(quinoline)] and trans-[PtCl2(NH3)(thiazole)] is formally equivalent to that by antitumor cisplatin, but different from clinically ineffective transplatin which preferentially forms these adducts between complementary guanine and cytosine residues. This result shows for the first time that simple chemical modification of the structure of an inactive compound alters its DNA binding site into a DNA adduct of an active drug.
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Biophysical studies on the stability of DNA intrastrand cross-links of transplatin
