In vitro bacterial bioluminescence coupled with a mediated electrochemical process of flavin on a viologen polymer electrode

Karatani, Hajime; Konaka, Taku

doi:10.1016/s0302-4598(98)00156-1

Cited by 6 publications

(3 citation statements)

References 31 publications

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“…The detachment of the flavin cofactor from the side-walls of SWNTs was realized by treating with a surfactant (sodium dodecyl sulfate (SDS)) or by reducing the attached FMN to FMNH 2 . These findings pave the way to ultimately link SWNTs with bacterial luciferase toward nanostructured bioluminescence devices, wherein the redox cycling of the flavin cofactor is electrically provided through the nanotube as opposed to the use of mediators …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Redox Behavior of Flavin Mononucleotide-Functionalized Single-Walled Carbon Nanotubes

Papadimitrakopoulos

2007

J. Am. Chem. Soc.

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In this contribution, we describe the synthesis and covalent attachment of an analogue of the flavin mononucleotide (FMN) cofactor onto carboxylic functionalities of single-walled carbon nanotubes (SWNTs). The synthesis of FMN derivative (12) was possible by coupling flavin H-phosphonate (9) with an aliphatic alcohol, using a previously unreported N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride coupling. We found that the flavin moiety of 12-SWNT shows a strong pi-pi interaction with the nanotube side-walls. This leads to a collapsed FMN configuration that quenches flavin photoluminescence (PL). The treatment of 12-SWNT with sodium dodecyl sulfate (SDS) overcomes this strong nanotube/isoalloxazine interaction and restores the FMN into extended conformation that recovers its luminescence. In addition, redox cycling as well as extended sonication were proven capable to temporally restore PL as well. Cyclic voltammetry of FMN onto SWNT forests indicated profound differences for the extended and collapsed FMN configurations in relation to oxygenated nanotube functionalities that act as mediators. These findings provide a fundamental understanding for flavin-related SWNT nanostructures that could ultimately find a number of usages in nanotube-mediated biosensing devices.

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Section: Introductionmentioning

confidence: 99%

“…These findings pave the way to ultimately link SWNTs with bacterial luciferase toward nanostructured bioluminescence devices, wherein the redox cycling of the flavin cofactor is electrically provided through the nanotube as opposed to the use of mediators. 23…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Redox Behavior of Flavin Mononucleotide-Functionalized Single-Walled Carbon Nanotubes

Papadimitrakopoulos

2007

J. Am. Chem. Soc.

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“…In contrast to the chemical reduction, the electrochemical reduction of FMN offers an easy to operate a contamination-free method for the reduction of FMN to FMNH2. 23,24,28 In the present study, the steady-state BL luminescence system developed by the present authors has been applied to examine the effects of hydrophobic molecules on the BL luminescence reaction. By using the proposed system, the effect of the alkyl chain-length of the n-alkylaldehyde substrate on the BL luminescence intensity was first examined.…”

Section: Introductionmentioning

confidence: 99%

Inhibition of Electrochemically Controlled Bioluminescence of Bacterial Luciferase by n-Alkyl Alcohols

2011

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An electrochemical system has been developed in order to assay the effect of hydrophobic molecules on the bioluminescence of bacterial luciferase (BL). The inhibition of BL luminescence by the long-chain n-alkyl alcohol has been examined using this system. The 1-heptanol, 1-octanol, 1-nonanol, 1-decanol, 1-undecanol and 1-dodecanol inhibited the BL reaction in a dose-dependent manner. The IC50 value, that is, the inhibitor concentration required to decrease the luminescence intensity by half, of these alcohols decreased with increasing the alkyl chain-length of the alcohols. In contrast, the shorter chain 1-hexanol did not inhibit the BL luminescence at all in the examined concentration range. These results indicate that the molecular size and hydrophobicity of the n-alkyl alcohol are the key factors to the inhibitory potency of the BL reaction. The IC50 values are in agreement with values obtained for the bioluminescence of the firefly luciferase system. The proposed electrochemical BL luminescence system will be used for an inhibitory assay of hydrophobic drugs, such as general anesthetics on protein functions.

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Steady-state bioluminescence of bacterial luciferase using electrochemical regeneration of flavin substrate and its application to inhibitory analysis

Yamasaki

Nakashima

Yamada

et al. 2009

Bioelectrochemistry

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In vitro bacterial bioluminescence coupled with a mediated electrochemical process of flavin on a viologen polymer electrode

Cited by 6 publications

References 31 publications

Synthesis and Redox Behavior of Flavin Mononucleotide-Functionalized Single-Walled Carbon Nanotubes

Synthesis and Redox Behavior of Flavin Mononucleotide-Functionalized Single-Walled Carbon Nanotubes

Inhibition of Electrochemically Controlled Bioluminescence of Bacterial Luciferase by n-Alkyl Alcohols

Steady-state bioluminescence of bacterial luciferase using electrochemical regeneration of flavin substrate and its application to inhibitory analysis

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