AN APPLICATION OF THE ARRAY OF LIPIDATED OLIGOPEPTIDES RESEMBLING ARTIFICIAL RECEPTORS FOR MOLECULAR RECOGNITION. THE STUDIES ON THE LIPOPHLILICITY OF SOME PIPERAZINES

Justyna Kolesińska 1Anna Musiał 2Barbara Malawska 2Zbigniew J. Kamiński 1

1. Technical University of Łódź, Institute of Organic Chemistry (PŁ), Żeromskiego 116, Łódź 90-924, Poland
2. Jagiellonian University, Collegium Medicum, Department of Pharmaceutical Chemistry, Medyczna 9, Kraków 30-688, Poland

Abstract

We found that supramolecular structures formed from N-acylated peptides attached on the a regular basis to the CH2OH groups on the surface of cellulose support via aminophenylamino-1,3,5-triazine very efficiently recognize small guests molecules, resembling the artificial receptors. In the contrary to the rigid structure of the most of artificial receptor described in the literature [1] (especially those, prepared by imprinting in the polymer matrix), the supramolecular structure is highly flexible. Thus, it is expected, that the host structures adjust their shape to fit the guests molecules most efficiently.
The array of the receptors wave been synthesized and used in the studies. Thus, even in the case, when the single receptor in a differential array does not necessarily have selectivity for a particular analyte, the combined fingerprint response can be extracted as a diagnostic pattern visually, or using chemometric tools.
In order to study the mechanism of the molecular recognition, we compared the selectivity of binding of triphenylmethyl dyes, Paclitaxel®, arylpiperazine derivatives with gradually increased lipophilicity and their fluorinated analogues respectively. Arylpiperazine derivatives have been chosen as model compounds with amide group, ester moiety, amine group, and lipophilic fragment in a molecule. These different fragment of a molecule, as well as lipophilicity might be responsible for interacting in a target site.
The interactions of colorless guest with the array were visualized by the subsequent processes of competitive adsorption-desorption of appropriate dye.
We found, that the binding process depends on the structure of amino-acids as well as lipidic fragment of the receptor and analyte structure. The complex nature of the host-guest interactions interactions will be discussed.
Acknowledgements: The study was supported by the Polish State Committee for Scientific Research under the Project 4-T09A 189 25.
[1] a) Zimmerman, S.C., et al. 2002. Synthetic hosts by monomolecular imprinting inside dendrimers. Nature 418, 399-403; b) Wright A.T.; Anslyn, E.V. , Differential receptor arrays and assays for solution-based molecular recognition, Chem. Soc. Rev., 2006, 35(1), 14-28.

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Presentation: Oral at V Multidyscyplinarna Konferencja Nauki o Leku, by Zbigniew J. Kamiński
See On-line Journal of V Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2006-02-21 09:54
Revised:   2009-06-07 00:44
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