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8624582 
Journal Article 
A Fluorescent Bisanthracene Macrocycle Discriminates between Matched and Mismatch-Containing DNA 
Granzhan, A; Teulade-Fichou, MP 
2009 
Yes 
Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 
WILEY-V C H VERLAG GMBH 
WEINHEIM 
15 
6 
1314-1318 
English 
19115291 
WOS:000263093800004 
The macrocyclic anthracene derivative that binds to matched and mismatched base pairs in DNA by distinct modes was investigated. The macrocycle was readily synthesized by a [2+2]-type cyclocondensation of anthracene-9,10- dicarboxaldehyde with 2,2'-oxybis(ethylamine), followed by the reduction of the macrocylic and conversion of the amine to a water-soluble hydrochloride salt. The two binding modes could be identified when the titration was performed with a mismatch-containing duplex I-TC. The absorption of the ligand rapidly decreased upon addition of I-TC up to a ligand-to-dna ratio of 4, which corresponds to binding of four ligand molecules to the duplex. The changes of fluorescence properties of macrocycle upon interaction with all 16 base-pair combinations of the duplexes I-YX were determined. It was observed that the probe is able to signal the presence of a single mismatched thymine residue in the duplexes that contain 16 other AT and GC pairs. 
Anthracenes; DNA mismatches; DNA recognition; Fluorescence; Macrocycles