LC–MS analysis in the e-beam and gamma radiolysis of metoprolol tartrate in aqueous solution: Structure elucidation and formation mechanism of radiolytic products

Slegers, Catherine; Maquille, Aubert; Deridder, Véronique; Sonveaux, Etienne; Jiwan, Jean-Louis Habib; Tilquin, Bernard

doi:10.1016/j.radphyschem.2006.02.001

Cited by 21 publications

(7 citation statements)

References 23 publications

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“…Next, the same nominal mass of two molecular ions at m/z 284 (mass shift of þ16 Da) and their elution at t R ¼ 6.1 and 6.8 min suggested the attachment of eOH group in different positions in the MTPL molecule, leading to different polarities of the formed intermediates. The mass spectra of these two products marked as P283-I and P283-II, respectively, are identical to the ones reported in Benner and Ternes (2009) and Slegers et al (2006). Thus implies that the hydroxylation occurred at the benzene ring and at the b-carbon in the methoxyethyl side chain, respectively.…”

Section: Structural Elucidation Of Electrochemical Oxidation Productssupporting

confidence: 75%

“…2). Products P225 (formed by N-dealkylation of MTPL) and P253 (formed by the cleavage of terminal methyl group) were previously reported as ozonation products of MTPL (Benner and Ternes, 2009), while P237 (formed by the cleavage of the terminal methoxy group) was one of the main products of e-beam and g-radiolysis of MTPL (Slegers et al, 2006). On the other hand, in CID experiments molecular ion m/z 134 was identified as a polar intermediate P133, formed by the cleavage of aromatic ether bond in the MTPL molecule ( Figure S1).…”

Section: Structural Elucidation Of Electrochemical Oxidation Productsmentioning

confidence: 84%

“…Further attack of ROS on the hydroxyl group resulted in the formation of P281-II. Most of the abovementioned products were previously identified as products of MTPL oxidation by OH -formed in radiolytic oxidation (Slegers et al, 2006;Song et al, 2008) and ozonation (Benner and Ternes, 2009). Scission of the aromatic ether bond and oxidative attacks at the methoxyethyl side chain by OH -were observed during electro-Fenton and photoelectron-Fenton treatment of MTPL (Isarain-Chavez et al, 2011).…”

Section: Fig 2 E Proposed Electrochemical Oxidation Pathways Of Metomentioning

confidence: 99%

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Electrochemical degradation of the β-blocker metoprolol by Ti/Ru0.7Ir0.3O2 and Ti/SnO2-Sb electrodes

2011

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BioassaysHalogenated by-product Micropollutant a b s t r a c t Electrochemical oxidation has been proposed for the elimination of pesticides, pharmaceuticals and other organic micropollutants from complex waste streams. However, the detrimental effect of halide ion mediators and the generation of halogenated by-products in this process have largely been neglected thus far. In this study, we investigated the electrochemical oxidation pathways of the b-blocker metoprolol in reverse osmosis concentrate (ROC) from a water reclamation plant using titanium anodes coated with Ti/SnO 2 -Sb exhibited higher oxidizing power for the same applied specific electrical charge, the generation of large fractions of chloro-, chloro-bromo-and bromo derivatives was observed for both electrode coatings. However, degradation rates of metoprolol and its degradation products were generally higher for the Ti/SnO 2 -Sb anode. Chemical analyses of metoprolol and its by-products were complemented with bioanalytical tools in order to investigate their toxicity relative to the parent compound. Results of the bioluminescence inhibition test with Vibrio fischeri and the combined algae test with Pseudokirchneriella subcapitata indicated a substantial increase in non-specific toxicity of the reaction mixture due to the formed halogenated by-products, while the specific toxicity (inhibition of photosynthesis) remained unchanged. ª 2011 Elsevier Ltd. All rights reserved. IntroductionThe unique ability of electrochemical processes to oxidize and/ or reduce organic compounds at controlled electrode potentials and using only electrons as reagents represents a great advantage over existing advanced oxidation processes (AOPs). Due to the generation of a variety of reactive oxygen species (ROS) at the anode (e.g. OH -, H 2 O 2 , O 2 , O 3 ), electrochemical oxidation is considered to be versatile and capable of oxidizing persistent organic micropollutants, nitrogen species and microorganisms (Comninellis et al., 2010). In recent years, there has been an increasing interest in applying electrochemical oxidation for the treatment of refractory waste streams such as landfill leachate and reverse osmosis concentrate (ROC) from water treatment processes (Anglada et al., 2009;Van Hege et al., 2004;Dialynas et al., 2008;Perez et al., 2010). Due to the high concentrations of organic contaminants, disposal of these streams represents a major problem as they require an on-site treatment. A v a i l a b l e a t w w w . s c i e n c e d i r e c t . c o m j o u r n a l h o m e p a g e : w w w . e l s e v i e r . c o m / l o c a t e / w a t r e s w a t e r r e s e a r c h 4 5 ( 2 0 1 1 ) 3 2 0 5 e3 2 1 40043-1354/$ e see front matter ª

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Section: Structural Elucidation Of Electrochemical Oxidation Productssupporting

confidence: 75%

Section: Structural Elucidation Of Electrochemical Oxidation Productsmentioning

confidence: 84%

Section: Fig 2 E Proposed Electrochemical Oxidation Pathways Of Metomentioning

confidence: 99%

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Electrochemical degradation of the β-blocker metoprolol by Ti/Ru0.7Ir0.3O2 and Ti/SnO2-Sb electrodes

2011

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“…To make such a verification a given drug should be irradiated with high doses of ionising radiation (γ, β, E-beam) whose effect should be tested by a number of analytical methods (chromatographic, spectrometric, thermal) permitting evaluation of radiochemical stability of a given drug, allowing observation of all kinds of changes and identification of the products of radiolysis [8][9][10] . Radiochemical stability of MT has been studied by other authors [11][12][13][14] , but the studies mainly concerned the influence of ionising radiation on water solutions of MT. In water solutions MT undergoes radiolysis after such a small dose of irradiation as 12.8 kGy.…”

Section: Introductionmentioning

confidence: 99%

The effect of ionizing radiation on metoprolol

Ogrodowczyk

Marciniec

Czwajda

2012

Drug Development and Industrial Pharmacy

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The influence of ionising radiation on physico-chemical properties of metoprolol tartrate (MT) in solid phase was studied. The compound was irradiated by radiation produced by a beam of high-energy electrons in an accelerator, in doses from 25 to 400 kGy, and the possible changes in the samples were detected by organoleptic analysis (colour, forms, clarity), chromatographic and spectrometric methods. Already at the standard sterilisation dose of 25 kGy, the presence of free radicals (0.3764 × 10(16) spin/g) and a decrease in the melting point by 1°C were noted. At higher doses of irradiation products of radiolysis appeared (100 kGy) and the colour was changed from white to pale cream (200 kGy). Our observation was that with increasing mass loss of MT after irradiation with 100, 200 and 400 kGy, the concentration of free radicals increased from 1.0330 to 1.6869 × 10(16) spin/g. The radiolytic yield of total radiolysis was 4.54 × 10(7) mol/J for 100 kGy, 7.42 × 10(7) mol/J for 200 kGy and 4.74 × 10(7) mol/J for 400 kGy. No significant changes were observed in the character of FT-IR spectra, but in UV an increase in intensity of the band at the analytical wavelength was noted. As follows from the results MT shows high radiochemical stability for the typical sterilisation doses 25-50 kGy, and will probably be able to be sterilised by radiation in the dose of 25 kGy.

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“…For the IS, the process of dissociation was much more complex. The collision produced more complicated fragments and several steps were likely involved in the process [14]. The probable fragmentation mechanism for the IS are proposed in Fig.…”

Section: Ms/ms Detectionmentioning

confidence: 99%

Sensitive quantification of rifaximin in human plasma by liquid chromatography–tandem mass spectrometry

Zhang

Duan

et al. 2007

Journal of Chromatography B

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LC–MS analysis in the e-beam and gamma radiolysis of metoprolol tartrate in aqueous solution: Structure elucidation and formation mechanism of radiolytic products

Cited by 21 publications

References 23 publications

Electrochemical degradation of the β-blocker metoprolol by Ti/Ru0.7Ir0.3O2 and Ti/SnO2-Sb electrodes

Electrochemical degradation of the β-blocker metoprolol by Ti/Ru0.7Ir0.3O2 and Ti/SnO2-Sb electrodes

The effect of ionizing radiation on metoprolol

Sensitive quantification of rifaximin in human plasma by liquid chromatography–tandem mass spectrometry

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