Chromatographic profiles of tryptophan and kynurenine enantiomers derivatized with (S)‐4‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐7‐(N,N‐dimethylaminosulfonyl)‐2,1,3‐benzoxadiazole using LC–MS/MS on a triazole‐bonded column

Iizuka, Hideaki; Harashima, Takuya; Takahashi, Shuhei; Kuwabara, Ryosuke; Naito, Yoko; Sakamoto, Tatsuya; Onozato, Mayu; Ichiba, Hideaki; Fukushima, Takeshi

doi:10.1002/chir.22726

Cited by 8 publications

(6 citation statements)

References 15 publications

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“…This was also the case for indirect chiral separation methods, which aim to quantify D-and L-amino acids. Several methods have been developed for the quantification of various D-AAs in different samples, such as D-Ser in plasma [62,65,87,111], DL-Cys and DL-homocysteine (DL-Hcy) [56,57], L-Trp and L-Kyn in serum [88,89], or some amino acids relevant to neurometabolomics, such as DL-Ser, DL-Asp, DL-Asn, DL-Glu, and DL-Gln [80].…”

Section: Targeted Analysis Methods For Amino Acidsmentioning

confidence: 99%

“…(S)-DBD-PyNCS was used for the derivatization of L-Trp and L-Kyn [88,89] in application to human serum samples. L-Trp and L-Kyn were determined with resolution values of 2.22 and 2.13, respectively, and excellent detection sensitivity by FL (in nM range) [89].…”

Section: Targeted Analysis Methods For Amino Acidsmentioning

confidence: 99%

“…for labeling amino acids and related metabolites [87][88][89], or α-hydroxy acids (D-and Llactic acid (LA)) [24], resulting in highly fluorescent reaction products. These derivatizing reagents are known to react with primary and secondary amines in the presence of triethylamine, forming fluorescent thiourea derivatives.…”

Section: N-(4-nitrophenoxycarbonyl)-l-phenylalanine 2-methoxyethyl Es...mentioning

confidence: 99%

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Indirect Enantioseparations: Recent Advances in Chiral Metabolomics for Biomedical Research

Bogos

Pralea

Moldovan

et al. 2022

IJMS

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Chiral metabolomics is starting to become a well-defined research field, powered by the recent advances in separation techniques. This review aimed to cover the most relevant advances in indirect enantioseparations of endogenous metabolites that were published over the last 10 years, including improvements and development of new chiral derivatizing agents, along with advances in separation methodologies. Moreover, special emphasis is put on exciting advances in separation techniques combined with mass spectrometry, such as chiral discrimination by ion-mobility mass spectrometry together with untargeted strategies for profiling of chiral metabolites in complex matrices. These advances signify a leap in chiral metabolomics technologies that will surely offer a solid base to better understand the specific roles of enantiomeric metabolites in systems biology.

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Section: Targeted Analysis Methods For Amino Acidsmentioning

confidence: 99%

Section: Targeted Analysis Methods For Amino Acidsmentioning

confidence: 99%

Section: N-(4-nitrophenoxycarbonyl)-l-phenylalanine 2-methoxyethyl Es...mentioning

confidence: 99%

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Indirect Enantioseparations: Recent Advances in Chiral Metabolomics for Biomedical Research

Bogos

Pralea

Moldovan

et al. 2022

IJMS

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“…Mouse serum samples for l -Trp and l -KYN measurements were prepared according to our previous report [ 39 , 40 ] with minor modifications. Briefly, l -Trp and l -KYN concentrations were determined using LC-MS/MS after derivatization with (R)-DBD-PyNCS.…”

Section: Methodsmentioning

confidence: 99%

Increased Indoleamine 2,3-Dioxygenase Levels at the Onset of Sjögren’s Syndrome in SATB1-Conditional Knockout Mice

Tanaka

Onozato

Mikami

et al. 2021

IJMS

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Sjögren’s syndrome (SS) is a chronic autoimmune disease characterized by dysfunction of salivary and lacrimal glands, resulting in xerostomia (dry mouth) and keratoconjunctivitis sicca (dry eyes). Autoantibodies, such as anti-SSA and anti-SSB antibodies, are hallmarks and important diagnostic factors for SS. In our previous study, we demonstrated that SS-like xerostomia was observed in SATB1 conditional knockout (SATB1cKO) mice, in which the floxed SATB1 gene was specifically deleted in hematopoietic cells as early as 4 weeks of age. In these mice, autoantibodies were not detected until 8 weeks of age in SATB1cKO mice, although exocrine gland function reached its lowest at this age. Therefore, other markers may be necessary for the diagnosis of SS in the early phase. Here, we found that mRNA expression of the interferonγ (IFN-γ) gene and the IFN-responsive indoleamine 2,3-dioxygenase (IDO) gene is upregulated in the salivary glands of SATB1cKO mice after 3 and 4 weeks of age, respectively. We detected l-kynurenine (l-KYN), an intermediate of l-tryptophan (l-Trp) metabolism mediated by IDO, in the serum of SATB1cKO mice after 4 weeks of age. In addition, the upregulation of IDO expression was significantly suppressed by the administration of IFN-γ neutralizing antibodies in SATB1cKO mice. These results suggest that the induction of IFN-dependent IDO expression is an initial event that occurs immediately after the onset of SS in SATB1cKO mice. These results also imply that serum l-KYN could be used as a marker for SS diagnosis in the early phases of the disease before autoantibodies are detectable.

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“…Using the derivatization reagent, ( R )‐DBD‐PyNCS, detection was performed using tandem MS (Iizuka et al, 2017; Takahashi et al, 2016) for the determination of Trp and KYN. In this case, a triazole‐phase column was found to be useful for the determination of both L ‐Trp and L ‐KYN in human serum or rat plasma.…”

Section: Kynureninementioning

confidence: 99%

A review of chromatographic methods for bioactive tryptophan metabolites, kynurenine, kynurenic acid, quinolinic acid, and others, in biological fluids

Fukushima

Umino

Sakamoto

et al. 2022

Biomedical Chromatography

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Kynurenine (KYN) is synthesized from an essential amino acid, tryptophan, by tryptophan 2,3-dioxygenase or indoleamine 2,3-dioxygenase via N-formyl-KYN in vivo.Subsequently, KYN acts as a precursor of some neuroactive metabolites such as kynurenic acid, quinolinic acid, and an important enzyme co-factor, nicotine adenine dinucleotide. These metabolites of tryptophan are a part of the 'kynurenine pathway.' In addition, KYN functions as an endogenous ligand for the aryl hydrocarbon receptor, which acts as a transcription factor. The levels of tryptophan metabolites are important for the assessment of the stage of neurological disorders, and therefore have garnered significant interest for clinical diagnosis. In this review, the detection of kynurenine, kynurenic acid, quinolinic acid, and other tryptophan metabolites performed via chromatographic methods such as HPLC using UV absorbance, fluorescence, and chromatographic-mass spectrometric detection is summarized.

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Chromatographic profiles of tryptophan and kynurenine enantiomers derivatized with (S)‐4‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐7‐(N,N‐dimethylaminosulfonyl)‐2,1,3‐benzoxadiazole using LC–MS/MS on a triazole‐bonded column

Cited by 8 publications

References 15 publications

Indirect Enantioseparations: Recent Advances in Chiral Metabolomics for Biomedical Research

Indirect Enantioseparations: Recent Advances in Chiral Metabolomics for Biomedical Research

Increased Indoleamine 2,3-Dioxygenase Levels at the Onset of Sjögren’s Syndrome in SATB1-Conditional Knockout Mice

A review of chromatographic methods for bioactive tryptophan metabolites, kynurenine, kynurenic acid, quinolinic acid, and others, in biological fluids

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