期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 10, 页码 3036-3056出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901999
关键词
antiproliferation; DNA recognition; intercalations; structure-activity relationships; RNA recognition
资金
- DFG (Deutsche Forschungsgemeinschaft)
- Fonds der Chemischen Industrie
- Alexander von Humboldt Foundation
- Ministry of Science, Education and Sport of Croatia [98-0982914-2918, 0980982464-2514]
- DAAD
We present a systematic study of different guanidiniocarbonylpyrrole-aryl derivatives designed to interact with DNA or RNA both through intercalation of an aromatic moiety into the base stack of the nucleotide and through groove binding of a guanidiniocarbonylpyrrole cation. We varied 1) the size of the aromatic ring (benzene, naphthalene, pyrene and acridine), 2) the length and flexibility of the linker connecting the two binding groups, and 3) the total number of positive charges present at different pH values. The compounds and their interactions with DNA and RNA were studied by UV/Vis, fluorescence and CD spectroscopy. Antiproliferative activities against human tumour cell lines were also determined. Our studies show that efficient interaction with, for example, DNA requires a significantly large aromatic ring (pyrene) connected through a flexible linker to the pyrrole moiety. However, a positive charge, as in 12, is also needed. Compound 12 allows for base-pair-selective recognition of ds-DNA at physiological pH values. The antiproliferative activities of these compounds correlate with their binding affinities towards DNA, suggesting that their biological effects are most probably due to DNA binding.
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