Calixarene Dimers as Host Molecules for Biologically Important Di‐ and Oligophosphates |
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Authors: | Reza Zadmard Dr Saeed Taghvaei‐Ganjali Dr Banafsheh Gorji Dr Thomas Schrader Prof?Dr |
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Institution: | 1. Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335‐186, Tehran (Iran), Fax: (+98)?21‐4458‐0762;2. Department of Chemistry, Islamic Azad University, North Tehran Branch, P.O. Box 15875‐5981, Tehran (Iran);3. Institut für Organische Chemie, Universit?t Duisburg‐Essen, Universit?tsstr. 5, 45117 Essen (Germany), Fax: (+49)?201‐183‐4252 |
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Abstract: | A dimeric calixarene, with an aliphatic C6‐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. |
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Keywords: | calixarenes DNA host– guest systems molecular ruler oligonucleotides |
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