Catalysis of electro-oxidation of antibiotics by nitroxyl radicals and the electrochemical sensing of vancomycin

Ono, Tetsuya; Sugiyama, Kazuko; Komatsu, S; Kumano, Masayuki; Yoshida, Kentaro; Dairaku, Takenori; Fujimura, Tsutomu; Sasano, Yusuke; Iwabuchi, Yoshiharu; Kashiwagi, Yoshitomo; Sato, Katsuhiko

doi:10.1039/d1ra03681e

Cited by 11 publications

(4 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Both ACT ( 2 ) and NNO have also been shown to be able to be used to detect vancomycin through this electrochemical method. 144 While the high reactivity of NNO is advantageous in many aspects, one limitation is that antibiotics with primary amines and thiols are not compatible. 50 Since ACT has been shown to be an effective electrochemical sensor, 4-trifluoromethylacetamido nitroxide ( 71 ) was investigated to detect vancomycin.…”

Section: New Horizons and Applications Of 1 Andmentioning

confidence: 99%

Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Bray,

Stephens,

Weierbach

et al. 2023

Chem. Commun.

View full text Add to dashboard Cite

show abstract

Section: New Horizons and Applications Of 1 Andmentioning

confidence: 99%

Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Bray,

Stephens,

Weierbach

et al. 2023

Chem. Commun.

View full text Add to dashboard Cite

show abstract

“…A trough level of 10 to 20 μg/mL (6.73 to 13.46 μM) has been proposed as a blood concentration during VCM treatment. Maintaining a safe blood concentration range is critical for the safe use of VCM, and monitoring is necessary to maintain efficacy and prevent problems [39]. The resulting calibration curve allowed electrochemical quantification of this concentration range of VCM.…”

Section: Nanopore Measurement Of Vcmmentioning

confidence: 99%

Vancomycin sensing using a phenylboronic acid‐modified nanopore pipette

Sato

Nakano

et al. 2023

Electroanalysis

Self Cite

View full text Add to dashboard Cite

Nanopore sensing measures the changes in charge and physical state around the nanopores as changes in ionic current. In this study, we performed vancomycin (VCM) sensing with nanopores modified via Au−S bonds with dithiobis(4‐butyrylamino‐m‐phenylboronic acid) (DTBA‐PBA), a derivative of phenylboronic acid (PBA) bearing a thiol. First, we modified a 3‐mm‐diameter Au electrode with a DTBA‐PBA self‐assembled monolayer (SAM) to confirm the VCM response of the PBA interface by cyclic voltammetry. DTBA‐PBA was then immobilized in the same manner on a nanopore pipette coated with an Au layer. We measured the VCM concentration from the change in ion current using the nanopore pipette. A VCM concentration‐dependent ionic current response was observed in the range of 0.01–1 mM. Many kinds of pharmaceuticals can bind to PBA; therefore, this method could be used for quick, easy, in situ quantification of not only VCM but also other pharmaceuticals with serious side effects.

show abstract

“…[6][7][8] We have focused on nitroxyl radical compounds, which can work as organocatalysts, to develop electrochemical sensors. [9][10][11][12][13] Nitroxyl radical compounds, such as 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), are used in combination with appropriate oxidants, such as NaClO, to catalyze the oxidation of alcohols in organic synthesis. 14,15) Alcohol can also be oxidized electrochemically by applying an electric potential instead of by oxidants.…”

Section: Introductionmentioning

confidence: 99%

“…We have also developed 3-hydroxy-8-azabicyclo[3.2.1] octane N-oxyl (3-HO-ABOO) (previously named nortropine N-oxyl (NNO), whereas here a more systematic name is used for clarity), and reported electrochemical sensing of glucose and drugs under physiological conditions based on these compounds. [9][10][11][12][13] We reported that 7-azabicyclo[2.2.1] heptan-7-ol (ABHOL), a highly active hydroxylamine catalyst with a new structure, exhibits high catalytic activity for alcohol oxidation under aerobic oxidation conditions using a copper salt as a co-catalyst. 23) ABHOL is oxidized to the corresponding nitroxyl radical (7-azabicyclo[2.2.1] heptane N-oxyl; ABHO) under oxidation reaction conditions and exhibits oxidation catalytic activity.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Characterization of a Novel Organoelectrocatalyst, 7-Azabicyclo[2.2.1]heptan-7-ol (ABHOL), and Its Application to Electrochemical Sensors

Toda,

Sugiyama,

Sato

et al. 2024

CHEMICAL & PHARMACEUTICAL BULLETIN

Self Cite

View full text Add to dashboard Cite

Electrochemical enzyme sensors are suitable for simple monitoring methods, for example, as glucose sensors for diabetic patients; however, they have several disadvantages arising from the properties of the enzyme. Therefore, nonenzymatic electrochemical sensors using functional molecules are being developed. In this paper, we report the electrochemical characterization of a new hydroxylamine compound, 7-azabicyclo[2.2.1]heptan-7-ol (ABHOL), and its application to glucose sensing. Although the cyclic voltammogram for the first cycle was unstable, it was reproducible after the second cycle, enabling electrochemical analysis of ethanol and glucose. In the first cycle, ABHOL caused complex reactions, including electrochemical oxidation and comproportionation with the generated oxoammonium ions. The electrochemical probe performance of ABHOL was more efficient than the typical nitroxyl radical compound, 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO), and had similar efficiency to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO), which is activated by the bicyclic structure. The results demonstrated the advantages of ABHOL, which can be synthesized from inexpensive materials via simple methods.

show abstract

Catalysis of electro-oxidation of antibiotics by nitroxyl radicals and the electrochemical sensing of vancomycin

Abstract: An analytical method using nitroxyl radicals was able to quantify vancomycin (VCM) in the concentration range of 10–100 μM, which is an important concentration range for drug monitoring in blood.

Cited by 11 publications

References 42 publications

Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Recent advancements in the use of Bobbitt's salt and 4-acetamidoTEMPO

Vancomycin sensing using a phenylboronic acid‐modified nanopore pipette

Electrochemical Characterization of a Novel Organoelectrocatalyst, 7-Azabicyclo[2.2.1]heptan-7-ol (ABHOL), and Its Application to Electrochemical Sensors

Contact Info

Product

Resources

About