Molecular recognition of nucleosides and nucleotides by a water-soluble cyclo-bis-intercaland receptor based on acridine subunits

Marie-Paule Teulade-fichou, Jean-Pierre Vigneron, Jean-Marie Lehn

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

71 Citations (Scopus)

Abstract

The macrocyclic bisacridine receptor I prepared by diamine-di-aldehyde condensation has been found to complex nucleotides strongly in water. The important changes of the fluorescence properties of 1 upon complexation revealed the remarkable ability of the receptor to discriminate between the two types of nucleobase: addition of purine nucleotides produced a strong quenching of the emission whereas a considerable enhancement of the fluorescence intensity was induced by pyrimidine nucleotides. By comparison with the binding properties of the acyclic monochromophoric reference compound 7 these opposite variations of the fluorescence have been interpreted in terms of electronic interaction (rc/7t stacking) and conformational changes of the receptor 1 (increase of the interchromophoric distance). The stability constants were determined by fluorescence measurements and high values ranging from 10<sup>4</sup> to 10<sup>8</sup> M<sup>1</sup> were obtained for the 1/1 complexes. The selec-tivities observed were shown to be dependent on both electrostatic and structural factors. © 1995, Taylor & Francis Group, LLC. All rights reserved.
Original languageEnglish
Pages (from-to)139-147
JournalSupramolecular Chemistry
Volume5
Issue number2
DOIs
Publication statusPublished - 1995
Externally publishedYes

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