Molecular recognition of acetylaminofluorene- and aminofluorene-modified guanosine

Citation
Ma. Santos et al., Molecular recognition of acetylaminofluorene- and aminofluorene-modified guanosine, SUPRAMOL CH, 11(3), 2000, pp. 201-215
Citations number
29
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
SUPRAMOLECULAR CHEMISTRY
ISSN journal
1061-0278 → ACNP
Volume
11
Issue
3
Year of publication
2000
Pages
201 - 215
Database
ISI
SICI code
1061-0278(2000)11:3<201:MROAAA>2.0.ZU;2-0
Abstract
New receptors based upon a carboxamidonaphthyridine unit derivatized with t he polyaromatic segments [4-(1-pyrenyl)butyroylamino] and [3(9-anthracenyl) propanoylamino] have been synthesized and studied by H-1 NMR titration in t heir binding interaction to the guanosine-C8 adducts from the carcinogens 2 -acetylaminofluorene and 2-aminofluorene. The high binding energy, in compa rison with that of the non-derivatized analogues, is rationalized in terms of a bi-site interaction (hydrogen bonding and aromatic stacking). Although many factors may contribute to the strength of the host-guest complexes de scribed herein, it appears that in some cases pi-pi interaction may induce a concomitant bending in the hydrogen bond system.