Steric control of DNA interstrand cross-link sites of trans platinum complexes: specificity can be dictated by planar nonleaving groups
Jazyk angličtina Země Německo Médium print
Typ dokumentu srovnávací studie, časopisecké články, práce podpořená grantem, Research Support, U.S. Gov't, Non-P.H.S.
PubMed
10907747
DOI
10.1007/pl00010665
Knihovny.cz E-zdroje
- MeSH
- adukty DNA metabolismus MeSH
- chinoliny chemie MeSH
- cisplatina metabolismus MeSH
- cytosin chemie MeSH
- DNA footprinting MeSH
- DNA chemie MeSH
- guanin chemie MeSH
- konformace nukleové kyseliny MeSH
- ligandy MeSH
- oligonukleotidy chemická syntéza chemie MeSH
- protinádorové látky chemie MeSH
- reagencia zkříženě vázaná chemie MeSH
- sekvence nukleotidů MeSH
- stereoizomerie MeSH
- thiazoly chemie MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Research Support, U.S. Gov't, Non-P.H.S. MeSH
- srovnávací studie MeSH
- Názvy látek
- adukty DNA MeSH
- chinoliny MeSH
- cisplatina MeSH
- cytosin MeSH
- DNA MeSH
- guanin MeSH
- ligandy MeSH
- oligonukleotidy MeSH
- protinádorové látky MeSH
- quinoline MeSH Prohlížeč
- reagencia zkříženě vázaná MeSH
- thiazoly 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
