Ferrocene-based Diels–Alder derivatization for the determination of 1α-hydroxyvitamin D3 in rat plasma by high-performance liquid chromatography–electrospray tandem mass spectrometry

Murao, Naoaki; Ishigai, Masaki; Sekiguchi, Nobuo; Takahashi, Tetsuo; Aso, Yoshinori

doi:10.1016/j.ab.2005.08.002

Cited by 23 publications

(23 citation statements)

References 24 publications

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“…The introduction of a proton‐affinitive or permanently charged moiety, such as a quaternary ammonium cation, at the 4‐position of TAD further enhances the detectability in the (+) ESI‐MS (Figure e–h). A Cookson‐type reagent having the easily oxidizable ferrocene residue [4‐ferrocenylmethyl‐TAD (Figure i)] has also been developed for the LC/(+) ESI‐MS/MS of a VD analog (Murao, Ishigai, Sekiguchi, Takahashi, & Aso, ). On the other hand, the introduction of an electron‐affinitive moiety, such as a nitro group [4‐(4‐nitrophenyl)‐TAD (Figure j)] (Higashi, Yamauchi, & Shimada, ) or pentafluorobenzyl group [4‐pentafluorobenzyl‐TAD (Figure k)] (Wang, Davis, Crews, Gabriel, & Edom, ) at the 4‐position of TAD is favorable for the electron capture APCI‐MS and particle‐beam negative ionization MS, respectively.…”

Section: Concept Of Cookson‐type Reagents For Biomedical Analysismentioning

confidence: 99%

Application of Cookson‐type reagents for biomedical HPLC and LC/MS analyses: a brief overview

Higashi

Shimada

2016

Biomedical Chromatography

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High-performance liquid chromatography (HPLC), LC/mass spectrometry (MS) and LC/tandem mass spectrometry (MS/MS) have been widely used for biomedical analyses, in which chemical derivatization is one of the most important methods to increase the sensitivity and selectivity. A Cookson-type reagent [4-substituted-1,2,4-triazoline-3,5-dione (4-substituted-TAD)] reacts with the compound bearing a conjugated diene, such as the vitamin D compound, to quantitatively form the stable Diels-Alder adduct. The reagent with a chromophore or fluorophore at the 4-position of TAD yields a highly responsive adduct for the UV or fluorescence detection, respectively. The Diels-Alder adduct with a Cookson-type reagent having a permanently charged, proton-affinitive or electron-affinitive moiety is sensitively detected by a specific MS analyzer. This paper is a brief overview of the applications of the reagents for biomedical analyses mainly using HPLC or LC/MS(/MS).

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Section: Concept Of Cookson‐type Reagents For Biomedical Analysismentioning

confidence: 99%

Application of Cookson‐type reagents for biomedical HPLC and LC/MS analyses: a brief overview

Higashi

Shimada

2016

Biomedical Chromatography

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“…In addition, pre- and post-column derivatization has been used to the enhance ionization efficiencies of vitamin D compounds. Cookson-type triazolinediones and triazolinediones-related reagents (e.g., 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD)) have been used as dienophiles to react with the cisoid diene moiety [35–40]. A further increase of the ionization efficiency of 25-OH D was achieved by adding methylamine to the mobile phase, after PTAD derivatization, as reported by Higashi et al [41].…”

Section: Introductionmentioning

confidence: 99%

Quantitative determination of vitamin D metabolites in plasma using UHPLC-MS/MS

et al. 2010

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Vitamin D is an important determinant of bone health at all ages. The plasma concentrations of 25-hydroxy vitamin D (25-OH D) and other metabolites are used as biomarkers for vitamin sufficiency and function. To allow for the simultaneous determination of five vitamin D metabolites, 25-OH D3, 25-OH D2, 24,25-(OH)2 D3, 1,25-(OH)2 D3, and 1,25-(OH)2 D2, in low volumes of human plasma, an assay using ultra-high-performance liquid chromatography–tandem mass spectrometry (UHPLC-MS/MS) was established. Plasma samples were spiked with isotope-labeled internal standards and pretreated using protein precipitation, solid-phase extraction (SPE) and a Diels–Alder derivatization step with 4-phenyl-1,2,4-triazoline-3,5-dione. The SPE recovery rates ranged from 55% to 85%, depending on the vitamin D metabolite; the total sample run time was <5 min. Mass spectrometry was conducted using positive ion electrospray ionization in the multiple reaction monitoring mode on a quadrupole–quadrupole-linear ion trap instrument after pre-column addition of methylamine to increase the ionization efficiency. The intra- and inter-day relative standard deviations were 1.6–4.1% and 3.7–6.8%, respectively. The limit of quantitation for these compounds was determined to be between 10 and 20 pg/mL. The 25-OH D results were compared with values obtained for reference materials (DEQAS). In addition, plasma samples were analyzed with two additional Diasorin antibody assays. All comparisons with conventional methods showed excellent correlations (r2 = 0.9738) for DEQAS samples, demonstrating the high degree of comparability of the new UHPLC-MS/MS technique to existing methods.

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“…A new Cookson-type reagent, 4-ferrocenylmethyl-1,2,4-triazoline-3,5-dione (FMTAD), has been developed for the determination of 1(OH)D 3 in rat plasma using LC-positive ESI-MS/MS [60] (Fig. 3b and Table 1).…”

Section: Determination Of Other Vitamin D Compoundsmentioning

confidence: 99%

Advances in determination of vitamin D related compounds in biological samples using liquid chromatography–mass spectrometry: A review

Higashi

Shimada

Toyo’oka

2010

Journal of Chromatography B

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Ferrocene-based Diels–Alder derivatization for the determination of 1α-hydroxyvitamin D3 in rat plasma by high-performance liquid chromatography–electrospray tandem mass spectrometry

Cited by 23 publications

References 24 publications

Application of Cookson‐type reagents for biomedical HPLC and LC/MS analyses: a brief overview

Application of Cookson‐type reagents for biomedical HPLC and LC/MS analyses: a brief overview

Quantitative determination of vitamin D metabolites in plasma using UHPLC-MS/MS

Advances in determination of vitamin D related compounds in biological samples using liquid chromatography–mass spectrometry: A review

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