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J Colloid Interface Sci. 2006 Apr 1;296(1):165-77. Epub 2005 Sep 15.

Synthesis and characterization of an electroactive surface that releases gamma-aminobutyric acid (GABA).

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  • 1Department of Chemical and Biomolecular Engineering, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave., Urbana, IL 61801, USA.


We report the synthesis and characterization of a new electroactive surface capable of releasing the neurotransmitter gamma-aminobutyric acid (GABA) upon reduction. The GABA was anchored to an alkanethiol via electrochemically active quinone (abbreviation, TM-GABA). The quinone unit, upon reduction to the hydroquinone, cyclizes to release GABA into solution. The half-life is 99 s. The self-assembled monolayer (SAM) of TM-GABA on gold was prepared and characterized with several surface sensitive techniques. X-ray photoelectron spectroscopy (XPS) explored the SAM formation of TM-GABA on Au surfaces. Cyclic voltammograms showed the ability to electrochemically control the quinone unit at the distal end of the chain. GABA was selectively released upon electrochemical reduction at a potential of -700 mV. The functional GABA terminal group was detected by surface plasmon resonance measurements of anti-GABA antibody binding.

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