4th EucheMs chemistry congress

Poster Session 2
s1243
chem. Listy 106, s257–s1425 (2012)
Poster session 2 - Nanochemistry, Nanotechnology
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deveLoPMent of veSiCLe-BASed
CheMoSenSorS: direCted funCtionALizAtion
of veSiCLe SurfACeS
A. MueLLer 1 , B. KoeniG 1
1 Institute of Organic Chemistry, University of Regensburg,
Regensburg, Germany
For the development of highly specific vesicle-based
chemosensors, a well defined two-dimensional assembly of
different binding sites on the spherical vesicle surface is necessary.
However, simple addition of the desired receptors to the
phospholipid mixture during vesicle preparation is subject to
restrictions: Firstly, suitable artificial amphiphilic receptor
molecules are needed – often only accessible by a tedious
synthesis. Secondly, based on previous works from our group, the
embedded binding sites are supposed to gather in tightly packed
patches due to phase separation. [1] This makes a directed receptor
assembly on the surface difficult. In order to overcome those
limitations, our approach relies on a subsequent controlled
attachment of receptors on unfunctionalized liposome
membranes, which are only modified with special binding
anchors. As a fast and reliable reaction for covalent fixation, the
UV light induced thiol–ene click reaction is used. This reaction
fulfills the essential requirement of water and oxygen tolerance
and exhibits biocompatibility. Here, we present preliminary results
from our investigations towards a defined receptor structuring on
vesicle surfaces.
references:
1. B. Gruber, S. Stadlbauer, A. Späth, S. Weiss, M. Kalinina,
B. König, Angew. Chem. Int. Ed. 2010, 49, 7125–7128.
Keywords: Supramolecular chemistry; Molecular recognition;
Vesicles; Sensors; Click chemistry;
4 th EucheMs chemistry congress
P - 0 7 6 2
‘MoLeCuLAr CLiP’ reCePtorS for
dihydroxyBenzeneS with SuitABLe BindinG
SiteS for enhAnCed CoPPer CoMPLexAtion
B. MurrAy 1 , J. MorAn 1 , J. MCGinLey 2
1 Institute of Technology Tallaght, Science, Dublin 24, Ireland
2 National University of Ireland Maynooth, Chemistry,
Maynooth Co. Kildare, Ireland
Email: brian.murray@ittdublin.ie
Urea-based Molecular Clips mimic natural receptors, with
an upper organic-cavity that binds to dihydroxybenzene (DHB)
molecules. [1] Many neurotransmitters such as dopamine contain a
DHB moiety.
The locking phenyl groups of the Molecular Clip hold it in
a convergent conformation for binding a DHB, but these groups
– with suitable modification can also serve as a binding site for
metals. The addition of nitrogen-containing groups here are ideal
for copper complexation [2] , whose ions play a large role in neural
functions. Elevated Cu2+ levels have been implicated in the
formation of protein plaques that are found in the neural tissue of
Alzheimer’s patients. [3] Such clips may act a model for the binding
and control of the redox states of copper, and protection of
DHB-type neurotransmitters.
Current work involves the addition of bipyridine moieties
to the lower locking phenyl ring system, and synthesis of new
benzil molecules which can be further functionalised to enhance
copper complexation.
references:
1. B. A. Murray and G. S. Whelan, Pure & Appl. Chem.
1996, 68, 1561-1567.
2. M. Kozien, PhD. Thesis, ITT Dublin, 2009.
3. A. Binolfi, G. R. Lamberto, R. Duran, L. Quintanar,
C. W. Bertoncini, J. M. Souza, C. Cervenansky,
M. Zweckstetter, C. Griesinger and C. O. Fernández,
J. Am. Chem. Soc., 2008, 130, 11801-11812.
Keywords: Supramolecular chemistry; Molecular recognition;
Dopamines; Copper; Allosterism;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc