Synthesis and application of library of artificial receptors immobilized on cellulose support

Justyna Frączyk 1Zbigniew J. Kamiński 1Agnieszka Mrozek 2

1. Technical University of Łódź, Institute of Organic Chemistry (PŁ), Żeromskiego 116, Łódź 90-924, Poland
2. Technical University of Łódź, Institute of General and Ecological Chemistry, Żwirki 36, Łódź 90-924, Poland

Abstract

We found that supramolecular structures formed by self-organisation of monolayer of
N-lipidated peptides attached to the CH2OH groups of cellulose support via aminophenylamino-1,3,5-triazine are able to create ”holes” and “pockets” in dynamic equilibrium, which can very efficiently recognized the structure (shape, size and polarity) of small guests molecules [1]. The supramolecular structures formed from N-lipidated peptide chains are highly flexible, therefore it has to be expected, that the host adjust its shape to fit the guest molecule most efficiently, resembling natural receptors. The array of the artificial receptors have 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 any chemometric tools [2]. The selectivity of binding was studied by experiments involving triphenylmethyl dyes. It has been found that any changes of size, polarity, hydrogen bonding ability of substituents of phenyl groups altered the binding profile. Based on this observation, we concluded that the selectivity of binding depends on the structure of peptide and lipidic fragment of the artificial receptor and vary with the analyte structure. An attempts were made to rationalise the relation between binding pattern and structure of receptor and analyte using SAR studies.

Acknowledgements: The study was supported by the Ministry of Science and High Education under the Research Project N N204 326737.

Literature: [1] a) Fraczyk, J.; Kaminski, Z.J. J. Comb. Chem. 10, 934-940 (2008). b) Frączyk, J.; Malawska, B.; Kaminski, Z. J. J. Comb. Chem., 11, 446-451 (2009). c) Frączyk, J; Kolesińska, B.; Czarnecka, A.; Malawska, B. Więckowska, A.; Bajda. M.; Kamiński, Z.J. QSAR & Comb. Sci. 28, 728-736 (2009). [2] Wright A.T.; Anslyn, E.V. Chem. Soc. Rev., 2006, 35(1), 14-28.

 

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Presentation: Poster at SMCBS'2009 International Workshop, by Justyna Frączyk
See On-line Journal of SMCBS'2009 International Workshop

Submitted: 2009-09-07 13:33
Revised:   2009-09-07 13:33