Assay of labile estrogen o-quinones, potent carcinogenic molecular species, by high performance liquid chromatography–electrospray ionization tandem mass spectrometry with phenazine derivatization

Yamashita, Kouwa; Masuda, Akina; Hoshino, Yuka; Komatsu, S; Numazawa, Mitsuteru

doi:10.1016/j.jsbmb.2010.02.016

Cited by 11 publications

(5 citation statements)

References 25 publications

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“…( 41 ) The confirmation of the novel quinone was performed by chemical trapping of the quinone by o -phenylenediamine to form the corresponding phenazine derivative. ( 43 , 44 ) In the presence of N -acetyl- l -cysteine, the quinone of 5HIAA adducted to the free thiol, but 5HIAA- N -acetyl- l -cysteine adduct was not confirmed, probably because of the short life-time of 5HIAA radicals compared with that of serotonin radicals (Fig. 5 B).…”

Section: Generation Of Quinones and Reaction Toward Biomoleculesmentioning

confidence: 95%

“…Chemical trapping for o -quinone by a diamine moiety can be applied to detect and quantify free o -quinone, as mentioned previously. ( 41 , 43 , 44 ) Quinone staining by incubation with nitroblue tetrazolium in alkaline glycinate buffer has been developed and applied for the detection of quinoproteins (quinone-adducted proteins). ( 47 , 48 ) The use of a biotinylated analog combined with (strepto)avidin-labeled enzyme/beads or an analog having an azide moiety for click chemistry is another alternative.…”

Section: Generation Of Quinones and Reaction Toward Biomoleculesmentioning

confidence: 99%

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Covalent adduction of endogenous and food-derived quinones to a protein: its biological significance

Kato

Suga

2018

J. Clin. Biochem. Nutr.

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There are many chemically reactive compounds, including quinone, in living systems and also food. Even after the ingestion of food polyphenols, quinones derived from catechol moieties could form endogenously in the body. Dopaquinone, dopamine quinone, estrogen-derived quinones, tryptamine-4,5-dione, and ubiquinone are examples of an endogenous quinone. These indicate that quinone is ubiquitously formed or present in living systems and food. Quinones can induce a variety of hazardous effects and also could have beneficial physiological effects. This review focuses on the chemical reactivity of quinone toward a biomolecule and its biological action.

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Section: Generation Of Quinones and Reaction Toward Biomoleculesmentioning

confidence: 95%

Section: Generation Of Quinones and Reaction Toward Biomoleculesmentioning

confidence: 99%

Covalent adduction of endogenous and food-derived quinones to a protein: its biological significance

Kato

Suga

2018

J. Clin. Biochem. Nutr.

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“…It is well known that o-phenylenediamine (OPD) is the most commonly used derivatization reagent for quantitative α-dicarbonyl compounds [113][114][115][116]. OPD reacts with α-dicarbonyl compounds, such as methylglyoxal, to produce stable 2-methylquinoxaline with high MS detection sensitivity [117].…”

Section: Aminesmentioning

confidence: 99%

“…MPIA can label aldehydes through reductive amination under weak acid condition to produce secondary amine derivatives without E-/Zisomers and few byproducts. As compared with the widely used DNPH, MPIA derivatives show higher sensitivity, which is probably attributed to the strong proton affinity of the lone pairs on imidazole nitrogen atom and the high hydrophobicity of MPIA derivatives.Different from monoamines, diamines react with α-dicarbonyl compounds to form cyclic compounds, so that a single derivatized product can be obtained without a reducing reagent.It is well known that o-phenylenediamine (OPD) is the most commonly used derivatization reagent for quantitative α-dicarbonyl compounds[113][114][115][116]. OPD reacts with α-dicarbonyl compounds, such as methylglyoxal, to produce stable 2-methylquinoxaline with high MS detection sensitivity[117].…”

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confidence: 99%

Progress and Challenges in Quantifying Carbonyl-Metabolomic Phenomes with LC-MS/MS

2021

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Carbonyl-containing metabolites widely exist in biological samples and have important physiological functions. Thus, accurate and sensitive quantitative analysis of carbonyl-containing metabolites is crucial to provide insight into metabolic pathways as well as disease mechanisms. Although reversed phase liquid chromatography electrospray ionization mass spectrometry (RPLC-ESI-MS) is widely used due to the powerful separation capability of RPLC and high specificity and sensitivity of MS, but it is often challenging to directly analyze carbonyl-containing metabolites using RPLC-ESI-MS due to the poor ionization efficiency of neutral carbonyl groups in ESI. Modification of carbonyl-containing metabolites by a chemical derivatization strategy can overcome the obstacle of sensitivity; however, it is insufficient to achieve accurate quantification due to instrument drift and matrix effects. The emergence of stable isotope-coded derivatization (ICD) provides a good solution to the problems encountered above. Thus, LC-MS methods that utilize ICD have been applied in metabolomics including quantitative targeted analysis and untargeted profiling analysis. In addition, ICD makes multiplex or multichannel submetabolome analysis possible, which not only reduces instrument running time but also avoids the variation of MS response. In this review, representative derivatization reagents and typical applications in absolute quantification and submetabolome profiling are discussed to highlight the superiority of the ICD strategy for detection of carbonyl-containing metabolites.

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“…Yamashita et al reported a sensitive and specific assay method for estrogen o-quinones using LC/ESI-MS/MS combined with the o-phenylenediamine-derivatization. 7) Brassinosteroids (vicinal diol-containing plant hormones) were also analyzed by a derivatization followed by LC/ESI-MS. 8) However, to the best of our knowledge, a practical derivatization procedure specific for the bioanalysis of steroids having a vicinal diol has not been reported.…”

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confidence: 99%

LC/MS/MS of Steroids Having Vicinal Diol as Electrospray-Active Boronates

Higashi

Kawasaki

Matsumoto

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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A derivatization procedure with (3-dimethylaminophenyl)dihydroxyborane (DAPB) was introduced to enhance the detectability of steroids having a vicinal diol in LC/electrospray ionization (ESI)-MS/MS. DAPB reacted with the vicinal diol on the steroids [4β-hydroxycholesterol (4-HCh), pregnanetriol (PT) and 20R,22R-dihydroxycholesterol] in pyridine at 50°C within 1 h. The resulting DAPB-derivatives were highly responsive in ESI-MS operating in the positive-ion mode and gave characteristic product ions during MS/ MS, which enabled sensitive detection using a selected reaction monitoring mode; the detection responses of the DAPB-derivatives were increased by 20-160-fold over those of the intact steroids and the limits of detection were in the low femtomole or attomole range. The derivatization procedure was successfully applied to biological sample analysis; the derivatization followed by LC/ESI-MS/MS enabled the specific detection of trace amounts of 4-HCh in human plasma and PT in human urine with a small sample volume, simple pretreatment and short chromatographic run time.Key words derivatization; electrospray ionization-MS/MS; steroid; vicinal diol; detectability A specific and sensitive method for the characterization and determination of endogenous steroids in biological fluids and tissues is useful for the elucidation of the nature, diagnosis and treatment of diseases. LC coupled with electrospray ionization (ESI)-MS/MS is widely used for steroid analysis due to its specificity, versatility and simultaneous multi-analyte quantification capability.1-3) However, not all steroids are suitable for ESI-MS/MS. One of the limitations in ESI-MS/MS for some steroids is the poor ionization and fragmentation behavior, leading to low sensitivity; current MS/MS instruments are extremely sensitive, but still their absolute sensitivity is analyte-dependent. To overcome this limitation, derivatization of the steroids has often been employed in LC/ESI-MS/ MS [4][5][6] ; a suitable derivatization can enhance the ionization efficiency of a poorly ionizable steroid in ESI-MS and assist fragmentation suitable for the selected reaction monitoring (SRM) mode.In most of the derivatization procedures reported until now, an ESI-active (proton-affinitive or permanently-charged) moiety is introduced to the target steroid through a hydroxyor an oxo-group. [4][5][6] These procedures have been proven to be very useful for LC/ESI-MS/MS of some steroids, but the derivatization utilizing a vicinal bifunctional group, such as vicinal diol and vicinal diketone, has not been fully examined. By such a derivatization, more specific detection and quantification of the target steroid may become possible. Yamashita et al. reported a sensitive and specific assay method for estrogen o-quinones using LC/ESI-MS/MS combined with the o-phenylenediamine-derivatization.7) Brassinosteroids (vicinal diol-containing plant hormones) were also analyzed by a derivatization followed by LC/ESI-MS. 8) However, to the best of our knowledge, a practical derivatization p...

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Assay of labile estrogen o-quinones, potent carcinogenic molecular species, by high performance liquid chromatography–electrospray ionization tandem mass spectrometry with phenazine derivatization

Cited by 11 publications

References 25 publications

Covalent adduction of endogenous and food-derived quinones to a protein: its biological significance

Covalent adduction of endogenous and food-derived quinones to a protein: its biological significance

Progress and Challenges in Quantifying Carbonyl-Metabolomic Phenomes with LC-MS/MS

LC/MS/MS of Steroids Having Vicinal Diol as Electrospray-Active Boronates

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