59042-34-1Relevant articles and documents
Synthesis of steroid bisglucuronide and sulfate glucuronide reference materials: Unearthing neglected treasures of steroid metabolism
Pranata, Andy,Fitzgerald, Christopher C.,Khymenets, Olha,Westley, Erin,Anderson, Natasha J.,Ma, Paul,Pozo, Oscar J.,McLeod, Malcolm D.
, p. 25 - 40 (2019/01/04)
Doubly or bisconjugated steroid metabolites have long been known as minor components of the steroid profile that have traditionally been studied by laborious and indirect fractionation, hydrolysis and gas chromatography-mass spectrometry (GC–MS) analysis. Recently, the synthesis and characterisation of steroid bis(sulfate) (aka disulfate or bis-sulfate) reference materials enabled the liquid chromatography-tandem mass spectrometry (LC–MS/MS) study of this metabolite class and the development of a constant ion loss (CIL) scan method for the direct and untargeted detection of steroid bis(sulfate) metabolites. Methods for the direct LC–MS/MS detection of other bisconjugated steroids, such as steroid bisglucuronide and mixed steroid sulfate glucuronide metabolites, have great potential to reveal a more complete picture of the steroid profile. However, access to steroid bisglucuronide or sulfate glucuronide reference materials necessary for LC–MS/MS method development, metabolite identification or quantification is severely limited. In this work, ten steroid bisglucuronide and ten steroid sulfate glucuronide reference materials were synthesised through an ordered combination of chemical sulfation and/or enzymatic glucuronylation reactions. All compounds were purified and characterised using NMR and MS methods. Chemistry for the preparation of stable isotope labelled steroid {13C6}-glucuronide internal standards has also been developed and applied to the preparation of two selectively mono-labelled steroid bisglucuronide reference materials used to characterise more completely MS fragmentation pathways. The electrospray ionisation and fragmentation of the bisconjugated steroid reference materials has been studied. Preliminary targeted ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) analysis of the reference materials prepared revealed the presence of three steroid sulfate glucuronides as endogenous human urinary metabolites.
PROGESTERONE RECEPTOR ANTAGONISTS AND USES THEREOF
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Page/Page column 45-46, (2011/11/30)
The present invention relates to a compound of formula (I): for its use as progesterone receptor antagonist, in particular for its use for the prevention and/or the treatment of cancer or uterine pathologies.
Potassium borohydride reductions of immobilised ketosteroids
Briggs, Josie C.,Hodge, Philip,Zhengpu, Zhang
, p. 3943 - 3956 (2007/10/03)
Ketosteroids absorbed into various insoluble supports (powdered polyethylene, microporous 2% crosslinked polystyrene beads, macroporous highly crosslinked polystyrene beads, silica gel and alumina) call be reduced using aqueous potassium barohydride. The use of phase transfer catalysts generally raises yields. In the case of 6-ketosteriods the supported reactions often follow a stereochemical course significantly different from that of analogous reactions in solution. This is attributed to the adsorbtion of the steroid onto the inner surfaces of the supports. In these cases reduction of (he ketosteroid by alkoxyborohydrides is substantially suppressed and thus most of the reduction is brought about by BH4- itself, a relatively sterically undemanding reductant. The net result is that whilst reductions of 6-ketosteroids in solution by potassium borohydride typically gives the 69α- and 6β-alcohols in the ratio 15:85, with the supported steroid the ratios can be as high as 90:10.
