Topologically constrained DNA intercalators: Synthesis and DNA binding studies

The synthesis and DNA binding properties of three macrocyclic diacridines (31, 32 and 33) is discussed. The two acridines are connected by linker chains at the 4- and 9-positions. Macrocycles 31 and 32 are linked via spermine at the 9-position and have been shown to bind to DNA by bisintercalation using absorption spectroscopy titrations, thermal denaturation studies, and viscometric titrations of both calf thymus DNA and closed circular supercoiled DNA. Macrocycle 31 dissociates 10 to 40 times slower from poly(d(A-T)) $\sb2$ and poly(d(G-C)) $\sb2$ than its analogous mono-linked analogue, spermine diacridine (7). $\sp1$H NMR studies of 31 complexed to d(CGCG)$\sb2$ indicate that the macrocycle binds to DNA by formation of a catenated complex in which one linking chain is located in opposite grooves of the DNA. The NMR studies and absorption spectral titrations suggest that 31 binds by insertion of the acridines on each side of one base pair in violation of the neighbor exclusion principle.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Lamberson, Carol R.

Contributors dc:contributor

• Zimmerman, Steven C.

• Chemistry, Organic

Statement dc:rights

• Copyright 1991 Lamberson, Carol R.

Language dc:language

eng

Identifier

AAI9136644
(UMI)AAI9136644

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/19162