Analysis of Phenothiazine and Its Derivatives Using LC/Electrochemistry/MS and LC/Electrochemistry/Fluorescence

Hayen, Heiko; Kärst, Uwe

doi:10.1021/ac0346050

Cited by 75 publications

(45 citation statements)

References 40 publications

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“…The mass spectrum contained many species which could readily be identified by comparison with the oxidation of the molecule phenothiazine [23]. Under identical experimental conditions the latter gave, by EC/MS at all pH values, the corresponding sulfoxide (m/z ¼ 216.0), the cation radical (m/z ¼ 199.0), the 3-H-phenothiazine-3-one (m/z ¼ 214.0) plus a dimer of PHZ with m/z ¼ 395.0 [23,25]. The chemical oxidation (PAA/KI) of PHZ produced at all pH values the PHZSO plus a small amount of 3-H-phenothiazine-3-one.…”

Section: Ec/ms Ec/lc/ms and Ec/lc/dadmentioning

confidence: 99%

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Electrochemical, Chemical and Enzymatic Oxidations of Phenothiazines

et al. 2005

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The oxidation of several phenothiazine drugs (phenothiazine, promethazine hydrochloride, promazine hydrochloride, trimeprazine hydrochloride and ethopropazine hydrochloride) has been carried out in aqueous acidic media by electrochemical, chemical and enzymatic methods. The chemical oxidation was performed in acetic acid with hydrogen peroxide or in formate buffers using persulfate. The enzymatic oxidation was performed in acetate or ammonium formate buffer by the enzyme horseradish peroxidase in the presence of H 2 O 2 . Molecules with, in the lateral chain, two carbon atoms (2C) separating the ring nitrogen and the terminal nitrogen, showed two parallel oxidation pathways, that is (i) formation of the corresponding sulfoxide and (ii) cleavage of the lateral chain with liberation of phenothiazine (PHZ) oxidized products (PHZ sulfoxide and PHZ quinone imine). Molecules with three carbon atoms (3C) separating the two nitrogens were oxidized to the corresponding sulfoxide. The chemical oxidation of all the studied molecules by hydrogen peroxide resulted in the corresponding sulfoxide with no break of the lateral chain. Oxidation by persulfate yielded, for the 3C derivatives, only the corresponding sulfoxide, but it produced cleavage of the lateral chain for the 2C derivatives. The origin of the distinct oxidation pattern between 2C and 3C molecules might be related to steric effects due to the lateral chain. The data are of interest in drug metabolism studies, especially for the early search. In the case of 2C phenothiazines, the results predict the possibility of an in vivo cleavage of the lateral chain with liberation of phenothiazine oxidized products which are known to produce several adverse side effects.

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Section: Ec/ms Ec/lc/ms and Ec/lc/dadmentioning

confidence: 99%

“…In the present work, taking into account the different literature data and with the help of powerful hyphenated instrumental techniques [23], we reinvestigate the oxidation reaction mechanisms of several structurally related phenothiazines (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Electrochemical, Chemical and Enzymatic Oxidations of Phenothiazines

et al. 2005

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“…1 Several methods have been applied to detect phenothiazine derivatives, such as spectrophotometry, 2 colorimetry, 3 liquid chromatography (LC) 4 and titrimetry. 5 Promethazine hydrochloride, a prominent compound in the large group of phenothiazine derivatives, is widely used as a therapeutic agent for treating various mental and personality disorder.…”

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confidence: 99%

Electrochemical Determination of Trace Promethazine Hydrochloride by a Pretreated Glassy Carbon Electrode Modified with DNA

et al. 2007

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Phenothiazines are a group of basic drugs that include a phenothiazine ring with different substituents attached at the 2-and 10-position, which are used as anti-psychotics, neuroleptics and antihistamines. 1 Several methods have been applied to detect phenothiazine derivatives, such as spectrophotometry, 2 colorimetry, 3 liquid chromatography (LC) 4 and titrimetry. 5 Promethazine hydrochloride, a prominent compound in the large group of phenothiazine derivatives, is widely used as a therapeutic agent for treating various mental and personality disorder. Daniela et al. 6 have reported the determination of promethazine hydrochloride in a pharmaceutical preparation using a flow-injection spectroelectroanalytical method. Lara et al. 7 utilized a capillary zone electrophoresis (CZE) technique for the quantitative analysis of three kinds of phenothiazines. The detection limit for promethazine hydrochloride was obtained to be 3.3 μg/mL; DPV and DC techniques were also applied to detect some phenothiazine drugs. 8 The quantification of drugs or drug monitoring based on DNA-drug interactions has been reported. [9][10][11][12] DNA is usually chosen as a surface-modification element because of its high sensitivity, and compatibility with modern micro-fabrication technologies; it is especially promising for rapid detection. 13,14 Measurements of some trace phenothiazine drugs were performed with a DNA-modified carbon paste electrode (CPE) by using a potentiometric stripping analysis (PSA) method. DNA-modified CPE permits measurements at low concentration levels of some phenothiazines with an accumulation step. 15 These previous studies suggested that a DNA-modified electrode might provide a very promising basis for determining trace promethazine.In the present work, DNA-modified electrode was assembled by immobilizing dsDNA onto the surface of a pretreated glassy carbon electrode (GCE(ox)). A pair of well-defined reversible redox peaks of promethazine was observed at low potential on the DNA/GCE(ox). The redox peak current was evaluated by using CV and DPV techniques. The signal was about 100-fold higher on DNA/GCE(ox) than that obtained on the DNA/GCE. By means of the redox peak currents of promethazine sensitively responding to the promethazine concentration, DNA/GCE(ox) could be applied to determine trace promethazine. The influence of a glassy carbon electrode pretreatment on the sensitivity of determining promethazine was considered. DNA/GCE(ox) was used to determine promethazine in healthy human serum with satisfactory results. Experimental Apparatus and reagentsElectrochemical measurements were performed with a CHI660A electrochemical analyzer (Shanghai Chenhua Apparatus Corporation, China). Glassy carbon electrodes (diameter 3 mm) and DNA modified glassy carbon electrodes were used as the working electrode, respectively. A platinum auxiliary electrode and an Ag/AgCl reference electrode were used for the measurements.Calf thymus (CT) DNA (Cat. No. D1501) and promethazine hydrochloride (Cat. No. P4651) were purchase...

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“…These include spectrofluorimetry [5], chemiluminescence [6], high performance liquid chromatography [7][8][9][10], voltammetry [11][12][13], differential pulse stripping voltammetry [14][15][16][17], polarography [18,19], and electrophoresis [20][21][22][23][24], visible spectrophotometry [25][26][27][28][29] and a combination of the previous ones [30]. These methods exhibit excellent selectivity, but require expensive instrumentation and are unsuitable for screening in the local under survey.…”

Section: Introductionmentioning

confidence: 99%

Disposable solid state probe for optical screening of chlorpromazine

Guerreiro

Sales

2011

Microchim Acta

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We are presenting a simple, low-cost and rapid solid-state optical probe for screening chlorpromazine (CPZ) in aquacultures. The method exploits the colourimetric reaction between CPZ and Fe(III) ion that occurs at a solid/liquid interface, the solid layer consisting of ferric iron entrapped in a layer of plasticized PVC. If solutions containing CPZ are dropped onto such a layer, a colour change occurs from light yellow to dark pink or even light blue, depending on the concentration of CPZ. Visual inspection enables the concentration of CPZ to be estimated. The resulting colouration was also monitored by digital image collection for a more accurate quantification. The three coordinates of the hue, saturation and lightness system were obtained by standard image processing along with mathematical data treatment. The parameters affecting colour were assessed and optimized. Studies were conducted by visible spectrophotometry and digital image acquisition, respectively. The response of the optimized probe towards the concentration of CPZ was tested for several mathematical transformations of the colour coordinates, and a linear relation was found for the sum of hue and luminosity. The limit of detection is 50 μM (corresponding to about 16 μg per mL). The probe enables quick screening for CPZ in real water samples with prior sample treatment.

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Analysis of Phenothiazine and Its Derivatives Using LC/Electrochemistry/MS and LC/Electrochemistry/Fluorescence

Cited by 75 publications

References 40 publications

Electrochemical, Chemical and Enzymatic Oxidations of Phenothiazines

Electrochemical, Chemical and Enzymatic Oxidations of Phenothiazines

Electrochemical Determination of Trace Promethazine Hydrochloride by a Pretreated Glassy Carbon Electrode Modified with DNA

Disposable solid state probe for optical screening of chlorpromazine

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