Fragmentation pathways of sulphonamides under electrospray tandem mass spectrometric conditions

Klagkou, Katerina; Pullen, Frank S.; Harrison, Mark E.; Organ, Andy; Firth, Alistair; Langley, G. John

doi:10.1002/rcm.1201

Cited by 73 publications

(61 citation statements)

References 27 publications

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“…The fragment ion with m/z 377 shows secondary fragmentation involving a rearrangement in the SO 2 group, resulting in the loss of SO to a fragment ion with m/z 329 and subsequent loss of C 2 H 6 to a fragment ion with m/z 299 (see Scheme 8). The rearrangement in the SO 2 group resulting in the loss of SO is also observed and extensively studied for sulphonamide antibiotics (Niessen, 1998;Klagkou et al, 2003;Sun, Dai, & Liu, 2008). Secondary fragmentation of the 1-methylpiperazine ring (m/z 99 or 100) leads to a fragment ion with m/z 58 (C 3 H 8 N þ ).…”

Section: Phosphodiesterase-5 Inhibitorsmentioning

confidence: 91%

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Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Niessen¹

2011

Mass Spectrometry Reviews

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The identification of drugs and related compounds by LC-MS-MS is an important analytical challenge in several application areas, including clinical and forensic toxicology, doping control analysis, and environmental analysis. Although target-compound based analytical strategies are most frequently applied, at some point the information content of the MS-MS spectra becomes relevant. In this article, the positive-ion MS-MS spectra of a wide variety of drugs and related substances are discussed. Starting point was an MS-MS mass spectral library of toxicologically relevant compounds, available on the internet. The positive-ion MS-MS spectra of ∼570 compounds were interpreted by chemical and therapeutic class, thus involving a wide variety of drug compound classes, such benzodiazepines, beta-blockers, angiotensin-converting enzyme inhibitors, phenothiazines, dihydropyridine calcium channel blockers, diuretics, local anesthetics, vasodilators, as well as various subclasses of anti-diabetic, antidepressant, analgesic, and antihistaminic drugs. In addition, the scientific literature was searched for available MS-MS data of these compound classes and the interpretation thereof. The results of this elaborate study are presented in this article. For each individual compound class, the emphasis is on class-specific fragmentation, as discussing fragmentation of all individual compounds would take far too much space. The recognition of class-specific fragmentation may be quite informative in determining the compound class of a specific unknown, which may further help in the identification. In addition, knowledge on (class-specific) fragmentation may further help in the optimization of the selectivity in targeted analytical approaches of compounds of one particular class.

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Section: Phosphodiesterase-5 Inhibitorsmentioning

confidence: 91%

“…1998; Klagkou et al, 2003;Sun, Dai, & Liu, 2008). Fragments with charge-retention at the other side of the molecule, for example, ions with m/z 74 and 57 (H 3 N þ C 4 H 9 and þ C 4 H 9 ) are observed as well.…”

Section: Fragmentation Of Toxicologically Relevant Drugsmentioning

confidence: 95%

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Niessen¹

2011

Mass Spectrometry Reviews

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“…Characteristic fragmentation pathways of sulfonamides°were°summarized,°for°instance°in°reference° [24]. After collisional activation of the [M ϩ H] ϩ ion of sulfadiazine, intense signals were observed at m/z 92, 108, and 156 (typical sulfonamide fragments) containing the sulfonamide moiety and at m/z 96 containing the aminopyrimidine ring.…”

Section: Resultsmentioning

confidence: 99%

Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments

Pfeifer¹,

Tuerk

Fuchs³

2005

J. Am. Soc. Mass Spectrom.

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Two major metabolites and one minor metabolite of sulfadiazine were found in pig manure, using a special combination of different MS techniques like parent and product ion scans, H/D exchange, accurate mass measurement, and MS/MS experiments with substructures. N4-acetylsulfadiazine and 4-hydroxysulfadiazine were identified as major metabolites. N4-acetylsulfadiazine could be verified by H/D exchange and comparison with product ion spectra of a synthetic reference compound. In the case of 4-hydroxysulfadiazine, the majority of possible isomers could be discounted after H/D exchange. Substructure-specific MS/MS experiments with fragment ions and comparison with product ion spectra of two references revealed the presence of 4-hydroxysulfadiazine. The minor metabolite was characterized to some degree using H/D exchange and tandem mass spectrometry in combination with a high-resolution time of flight mass spectrometer. The aminopyrimidine moiety contained an additional modification with a likely elemental composition of . Antibiotics and antimicrobial agents are used for both therapeutic and prophylactic purposes in addition to their application as growth promoters. The antimicrobial sulfonamides are one class of pharmaceuticals that is widely used. As a consequence, these compounds have been found in surface and ground water, liquid manure, and soil [3][4][5][6][7][8][9][10][11][12]. After administration to animals, the majority of the pharmaceuticals used are excreted unchanged or as phase I and phase II metabolites. As part of an environmental risk assessment, these metabolites also have to be characterized because phase I metabolites can still be active against bacteria and phase II metabolites can be converted back to the parent drug or phase I metabolites. Moreover, very little is known about the capacity of microbiological decay and the occurrence of new metabolites after incubation for several months in a manure tank.There are only a few references describing the metabolism of sulfadiazine in pigs [13,14]. After intravenous administration of 40 to 60 mg sulfadiazine per kg body weight to male pigs without coadministration of trimethoprim, only low levels of metabolites have been observed. The N-acetyl sulfadiazine was the main metabolite in plasma. Traces of 4-hydroxysulfadiazine were also detected. N-acetyl sulfadiazine and 4-hydroxysulfadiazine were the major metabolites in urine collected up to three hours after application. No further metabolites were identified and investigations in feces were not carried out.The aim of the present work was to use different mass spectrometric strategies to identify possible metabolites of the widely used drug sulfadiazine in manure originating from a pig farm. The metabolites of interest should still have a similar structure as the parent drug and, therefore, retain to a greater or lesser extent their bioactive profile against micro-organisms. Earlier investigations about the biological activity of metabolites showed action of hydroxylated metabolites of sulfadiazine ag...

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“…Q-TOF-MS is also useful to elucidate fragmentation processes of polar pollutants [214]. Because of its high resolution and good sensitivity over a full mass range, TOF-MS would seem to be advantageous for screening purposes.…”

Section: Time-of-flight Msmentioning

confidence: 99%

Analytical Methods for Polar Pollutants

Reemtsma

Quintana

2006

Organic Pollutants in the Water Cycle

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Fragmentation pathways of sulphonamides under electrospray tandem mass spectrometric conditions

Cited by 73 publications

References 27 publications

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Fragmentation of toxicologically relevant drugs in positive‐ion liquid chromatography–tandem mass spectrometry

Structural characterization of sulfadiazine metabolites using H/D exchange combined with various MS/MS experiments

Analytical Methods for Polar Pollutants

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