Mass spectrometric detection of and similarities between 1-androgens

Verheyden, K.; Bizec, Bruno Le; Courtheyn, D.; Mortier, Virginie; Vandewiele, M.; Gillis, W. A.; Vanthemsche, P.; Brabander, H.F. De; Noppe, H.

doi:10.1016/j.aca.2006.10.058

Cited by 12 publications

(12 citation statements)

References 7 publications

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“…Although 1‐ene and 4‐ene‐3‐keto anabolic steroids exhibited a similar fragmentation at low collision energies in the examined region ( m/z ≥M–100), a different fragmentation behaviour at higher collision energy was observed. This difference has also been previously reported for 1‐ene‐3‐keto anabolic steroids 11, 22. In all cases, one abundant product ion was present that could be related to a three‐ring structure including the B‐, C‐ and D‐rings.…”

Section: Resultssupporting

confidence: 81%

Collision‐induced dissociation of 3‐keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation

Pozo

Eenoo

Deventer

et al. 2008

Rapid Comm Mass Spectrometry

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The collision-induced dissociation of forty-one 3-keto anabolic steroids and related compounds has been studied using both triple quadrupole (QqQ) and hybrid quadrupole-time of flight (QTOF) instruments. Due to the complexity of the product ion spectra of these analytes, which generate a large number of ions, only two specific regions were studied in depth: the product ions near the precursor ion (m/z > or =M-100) and the most abundant product ions at a collision energy of 30 eV. Accurate mass measurements were used in order to obtain an unequivocal assignment of the empirical formula and the origin of each selected product ion. Analytes have been divided into eight groups according to the number and position of double bonds and the presence of functional groups such as hydroxyl- or nitrogen-containing rings. A correlation between the steroid structure and the product ions obtained has been postulated. The application of these correlations can be useful in the elucidation of feasible structures for unknown steroids and/or their metabolites.

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Section: Resultssupporting

confidence: 81%

Collision‐induced dissociation of 3‐keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation

Pozo

Eenoo

Deventer

et al. 2008

Rapid Comm Mass Spectrometry

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“…This fact suggests the presence of a steroid with low conjugation in C3 and therefore reduction of the Δ 4 is the most feasible structure for Cys4. The presence of several specific ions such as m/z 69, or losses of 84 Da and 102 Da supports this assignment . The synthesis of the Cys conjugate of (5α)‐1‐androstenedione showed similar fragmentation pathway but with different abundances and eluting at different retention time.…”

Section: Resultsmentioning

confidence: 59%

“…The product ion of NAC5 at low collision energy exhibited the common loss of 163 Da and the ions at m/z 164. At higher collision energies, the occurrence of the ion at m/z 187, m/z 205 and m/z 69 (Table ) suggested the presence of a 1‐ene‐3‐keto moiety in the free AAS . NAC conjugates of 5α and 5β isomers of 1‐testosterone were synthesized.…”

Section: Resultsmentioning

confidence: 99%

Detection and characterization of urinary metabolites of boldione by LC‐MS/MS. Part II: Conjugates with cysteine and N‐acetylcysteine

Pozo

Gómez

Marcos

et al. 2012

Drug Testing and Analysis

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The occurrence of boldione metabolites conjugated with cysteine and N-acetylcysteine in human urine was evaluated. Methods based on precursor ion scan of the protonated aminoacid (m/z 122 and m/z 164 for cysteine and N-acetylcysteine respectively) and neutral losses of the aminoacids (121 Da and 163 Da for cysteine and N-acetylcysteine respectively) were applied for the open detection of conjugates. Results for urine samples collected before and after boldione administration were compared. Using this approach, 24 metabolites (eleven conjugates with cysteine and thirteen conjugated with N-acetylcysteine) were detected. The metabolites were characterized by mass spectrometry and their potential structures were proposed based on this information. The structures of nine of these metabolites were confirmed by the synthesis of the conjugates. According to these results, a metabolic pathway for boldione involving this type of conjugation was presented. Up to our knowledge this is the first time that cysteine conjugates are presented for exogenous anabolic androgenic steroids and the first report of N-acetylcysteine conjugates for steroids.

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“…In addition to steroids such as tetrahydrogestrinone, which was specifically designed to evade detection [102], numerous steroidal 'prodrugs' have become available on the internet [103][104][105][106]. These are, in effect, designer steroids, the structures of which are intended to circumvent USA laws.…”

Section: Future Perspectivementioning

confidence: 99%

Metabolism of Anabolic Steroids and Their Relevance to Drug Detection in Horseracing

Teale¹,

Houghton²

2010

Bioanalysis

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The fight against doping in sport using analytical chemistry is a mature area with a history of approximately 100 years in horseracing. In common with human sport, anabolic/androgenic steroids (AASs) are an important group of potential doping agents. Particular issues with their detection are extensive metabolism including both phase I and phase II. A number of the common AASs are also endogenous to the equine. A further issue is the large number of synthetic steroids produced as pharmaceutical products or as 'designer' drugs intended to avoid detection or for the human supplement market. An understanding of the metabolism of AASs is vital to the development of effective detection methods for equine sport. The aim of this paper is to review current knowledge of the metabolism of appropriate steroids, the current approaches to their detection in equine sport and future trends that may affect equine dope testing.

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Mass spectrometric detection of and similarities between 1-androgens

Cited by 12 publications

References 7 publications

Collision‐induced dissociation of 3‐keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation

Collision‐induced dissociation of 3‐keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation

Detection and characterization of urinary metabolites of boldione by LC‐MS/MS. Part II: Conjugates with cysteine and N‐acetylcysteine

Metabolism of Anabolic Steroids and Their Relevance to Drug Detection in Horseracing

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