Synthesis and characterization of an electroactive surface that releases gamma-aminobutyric acid (GABA).
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.
Yan
Chun
C
Department of Chemical and Biomolecular Engineering, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave., Urbana, IL 61801, USA. cyan@uiuc.edu
Matsuda
Wakana
W
Pepperberg
David R
DR
Zimmerman
Steven C
SC
Leckband
Deborah E
DE
D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013499:Surface Properties; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D001672:Biocompatible Materials; D013438:Sulfhydryl Compounds; C515088:TM-GABA; D005680:gamma-Aminobutyric Acid