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

Yan, Changfeng; Matsuda, Wakana; Pepperberg, David R.; Zimmerman, Steven C.; Leckband, Deborah

doi:10.1016/j.jcis.2005.08.029

Cited by 10 publications

(5 citation statements)

References 45 publications

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“…We , and others , previously reported that the two-electron reduction of various quinone trimethyl-lock ( Q3 ) systems by chemical agents (Na 2 S 2 O 4 or NaBH 4 ) or electrolysis produces the corresponding hydroquinone, HQ3 , possessing a sterically congested configuration, and HQ3 spontaneously dissociates from the parent structure as the lactone 3-HQ3 . On the basis of time-course data that exhibit an immediate increase in fluorescence intensity of calcein following the addition of the reducing agent Na 2 S 2 O 4 to the calcein-loaded 1-Q3 liposomes (Figure , Curve A), chemical reduction of liposomal 1-Q3 to 1-HQ3 resulted in the liberation of encapsulated calcein from the carrier!…”

Section: Resultsmentioning

confidence: 99%

Redox-Triggered Contents Release from Liposomes

et al. 2008

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An exciting new direction in responsive liposome research is endogenous triggering of liposomal payload release by overexpressed enzyme activity in affected tissues and offers the unique possibility of active and site-specific release. Bringing to fruition the fully expected capabilities of this new class of triggered liposomal delivery system requires a collection of liposome systems that respond to different upregulated enzymes; however, a relatively small number currently exist. Here we show that stable, ~100 nm diameter liposomes can be made from previously unreported quinone-dioleoyl phosphatidylethanolamine (Q-DOPE) lipids, and complete payload release (quenched fluorescent dye) from Q-DOPE liposomes occurs upon their redox activation when the quinone headgroup possesses specific substituents. The key component of the triggerable, contents-releasing Q-DOPE liposomes is a “trimethyl-locked” quinone redox switch attached to the N-terminus of DOPE lipids that undergoes a cleavage event upon two-electron reduction. Payload release by aggregation and leakage of “uncapped” Q-DOPE liposomes is supported by results from liposomes wherein deliberate alteration of the “trimethyl-locked” switch completely deactivates the redox-destructible phenomena (liposome opening). We expect that Q-DOPE liposomes and their variants will be important in treatment of diseases with associated tissues that overexpress quinone reductases, such as cancers and inflammatory diseases, because the quinone redox switch is a known substrate for this group of reductases.

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Section: Resultsmentioning

confidence: 99%

Redox-Triggered Contents Release from Liposomes

et al. 2008

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“…Like other redox-active SAMs, these monolayers take advantage of the redox properties of quinones to confer some particular functionalities to the modified surface. For example, quinones have been used as building blocks for electrochemically controlled post-assembly strategies [3][4][5][6][7][8][9] or, conversely, for the electrochemically triggered release of biochemical ligands [10,11].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Bouffier

Lister

Higgins

et al. 2012

Journal of Electroanalytical Chemistry

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“…4 Biofunctionalization using neurotransmitters is a new research area, which holds the promise of a multitude of technical and medical applications. [5][6][7][8][9] We consider the immobilization of neurotransmitters by chemisorption to surfaces with the aim to create model systems for the development of technologies to accomplish molecular recognition and drug screening. In previous work, we have presented investigations on a tyrosine and a dopamine analogue.…”

Section: Introductionmentioning

confidence: 99%

“…Biofunctionalization using neurotransmitters is a new research area, which holds the promise of a multitude of technical and medical applications. − …”

Section: Introductionmentioning

confidence: 99%

Noradrenaline and a Thiol Analogue on Gold Surfaces: An Infrared Reflection−Absorption Spectroscopy, X-ray Photoelectron Spectroscopy, and Near-Edge X-ray Absorption Fine Structure Spectroscopy Study

et al. 2010

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Self-assembled monolayers and multilayers of a noradrenaline analogue (Nor-Pt) on gold substrates as well as multilayers of noradrenaline have been investigated by means of the molecular orientation, the molecule−surface interaction, the molecular composition and the functional group availability for further biointeraction processes, using X-ray photoelectron spectroscopy (XPS), infrared reflection−absorption spectroscopy (IRAS), and near-edge X-ray absorption fine structure (NEXAFS) spectroscopy. A chemical shift (1.7 eV) of the S 2p peak to lower binding energies is observed, in the XPS spectrum, indicating that the Nor-Pt molecules are chemisorbed onto the gold substrate. The IR results show that Nor-Pt adsorbate has the CO stretching vibration modes parallel oriented relative to the gold substrate. The average tilt angle of the aromatic ring relative to the gold surface normal is determined to be approximately 51°, based on the NEXAFS measurements on Nor-Pt monolayers. The experimental results and assignments are supported with theoretical studies where we use the building block principle in the spectral analysis and compare with the measurements of noradrenaline and Nor-Pt. The theoretical calculations are shown to be useful; for angle dependence NEXAFS studies as resonances with fully π* or σ* character are preferred for correct analysis.

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

Cited by 10 publications

References 45 publications

Redox-Triggered Contents Release from Liposomes

Redox-Triggered Contents Release from Liposomes

Electrochemical investigations of dissolved and surface immobilised 2-amino-1,4-naphthoquinones in aqueous solutions

Noradrenaline and a Thiol Analogue on Gold Surfaces: An Infrared Reflection−Absorption Spectroscopy, X-ray Photoelectron Spectroscopy, and Near-Edge X-ray Absorption Fine Structure Spectroscopy Study

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