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Calixarene Dimers as Host Molecules for Biologically Important Di‐ and Oligophosphates
Author(s) -
Zadmard Reza,
TaghvaeiGanjali Saeed,
Gorji Banafsheh,
Schrader Thomas
Publication year - 2009
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200900085
Subject(s) - calixarene , dimer , chemistry , cationic polymerization , molecule , supramolecular chemistry , stereochemistry , crystallography , fluorescence , polymer chemistry , organic chemistry , physics , quantum mechanics
A dimeric calixarene, with an aliphatic C 6 ‐bridge and six anilinium head groups at its upper rim, preferably complexes diphosphates and oligonucleotides with more than 10 bonds between both anionic moieties. Free binding energies correlate with the length of the aliphatic bridge in a roughly linear fashion. The binding event, which is monitored by fluorescence titrations and competition experiments, relies on Coulomb interactions, as opposed to a nonpolar variant with tert ‐butyl instead of ammonium groups; here, hydrophobic forces prevail, rendering the calixarene dimer selective for less polar cofactors such as FAD. The best guest for the hexaanilinium dimer is found in ssDNA, which carries multiple copies of the optimal trinucleotide for maximum attraction towards the extended cationic host. The recognition event is also observed in the environment of a lipid monolayer, and provides a means to quantify dimer diphosphate interactions by measuring p/A shifts.