Bis-4-aminoquinolines: novel triple-helix DNA intercalators and antagonists of immunostimulatory CpG-oligodeoxynucleotides.
Six dimeric 2-(2-naphthyl)quinolin-4-amines with a linker between the amino groups and eight dimeric 2-(4-anilino)quinolin-4-amines linked between the anilino groups were synthesized and evaluated for their interaction with duplex/triplex DNA's and as antagonists of immunostimulatory oligodeoxynucleotides with a CpG-motif (CpG-ODN). The most powerful triple-helix DNA intercalator known to date, with high affinity toward T.A.T triplets and triplex/duplex selectivity, was found. The potent antagonism of immunostimulatory CpG-ODN by several bis-4-aminoquinolines is not related to their DNA interactions.
Strekowski
Lucjan
L
Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA. lucjan@gsu.edu
Say
Martial
M
Zegrocka
Oliwia
O
Tanious
Farial A
FA
Wilson
W David
WD
Manzel
Lori
L
Macfarlane
Donald E
DE
D000276:Adjuvants, Immunologic / Q000037:antagonists & inhibitors* / Q000494:pharmacology; D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D004247:DNA / Q000378:metabolism; D007202:Indicators and Reagents; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D009838:Oligodeoxyribonucleotides / Q000037:antagonists & inhibitors* / Q000494:pharmacology; D009841:Oligonucleotides / Q000037:antagonists & inhibitors* / Q000494:pharmacology
D000276:Adjuvants, Immunologic; D000634:Aminoquinolines; C408982:CPG-oligonucleotide; D007202:Indicators and Reagents; D007364:Intercalating Agents; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; D004247:DNA