Synthesis and structure-DNA binding relationship analysis of DNA triple-helix specific intercalators.
4-[N-(Aminoalkyl)amino]-2-arylquinolines with conformational freedom around positions 2 and 4 of the quinoline stabilize strongly poly(dT.dA.dT) (triplex DNA) and bind weakly to poly-(dA.dT) (duplex DNA). Basicity of N1 of the quinoline parallels the interaction strength of these compounds with the triple-helical DNA structure suggesting that N1 of the quinoline is protonated in the complex with the DNA triplex. The experimental results support the interaction model suggested previously.
Strekowski
L
L
Department of Chemistry, Georgia State University, Atlanta 30303, USA.
Gulevich
Y
Y
Baranowski
T C
TC
Parker
A N
AN
Kiselyov
A S
AS
Lin
S Y
SY
Tanious
F A
FA
Wilson
W D
WD
D004247:DNA / Q000737:chemistry* / Q000378:metabolism*; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000378:metabolism*; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D011071:Poly T / Q000378:metabolism; D011067:Poly dA-dT / Q000378:metabolism; D011804:Quinolines / Q000737:chemistry* / Q000378:metabolism; D013053:Spectrophotometry; D013329:Structure-Activity Relationship; D013816:Thermodynamics
D007364:Intercalating Agents; D011804:Quinolines; D011071:Poly T; D011067:Poly dA-dT; D004247:DNA