Simple and practical derivatization procedure for enhanced detection of carboxylic acids in liquid chromatography–electrospray ionization-tandem mass spectrometry

Higashi, Tatsuya; Ichikawa, Takuya; Inagaki, Shinsuke; Min, Jun Zhe; Fukushima, Takeshi; Toyo’oka, Toshimasa

doi:10.1016/j.jpba.2010.03.001

Cited by 108 publications

(72 citation statements)

References 21 publications

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“…SecoA-COOH and SecoB-COOH (structures, see Fig. 7 ) were analyzed by LC-MS/MS after derivatization with 2-picolylamine (PA) ( 23 ). Briefl y, aliquots of extracted samples were dissolved in acetonitrile (100 µl).…”

Section: Analysis Of Secosterols By Lc-ms/msmentioning

confidence: 99%

Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway

Tomono

Miyoshi

Shiokawa

et al. 2011

Journal of Lipid Research

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myeloperoxidase-dependent pathway. J. Lipid Res. 2011. 52: 87-97. Supplementary key words secosterol • neutrophils • myeloperoxidase • infl ammationA reactive species with a chemical signature similar to that of ozone has been proposed to be generated by the antibody-catalyzed oxidation of water with singlet oxygen during the oxidative burst of activated human neutrophils and in infl amed tissues ( 1, 2 ). The formation of an ozonelike oxidant from singlet oxygen by neutrophils can be catalyzed not only by antibodies but also by amino acids such as tryptophan, methionine, and cysteine ( 3 ). To prove the formation of an ozone-like oxidant by neutrophils, previous studies used chemical reactions, such as the conversion of indigo carmine to isatin sulfonic acid or the oxidation of vinylbenzoic acid to 4-carboxybenzaldehyde. However, these reactions are not suffi ciently specifi c to ozone to conclude an ozone production by neutrophils ( 4, 5 ).Further evidence for ozone formation in vivo was based on the detection and formation of the cholesterol ozonolysis products 3 ␤ -hydroxy-5-oxo-5,6-secocholestan-6-al (secosterol-A, also called atheronal-A) and its aldolization product 3 ␤ -hydroxy-5 ␤ -hydroxy-B-norcholestane-6 ␤ -carboxaldehyde (secosterol-B, also called atheronal-B) in human tissues. These secosterols were previously reported to be formed only by ozone among the various reactive oxygen species (ROS) such as singlet oxygen, superoxide anion, hydroxyl Abstract 3 ␤ -Hydroxy-5-oxo-5,6-secocholestan-6-al (sec osterol-A) and its aldolization product 3 ␤ -hydroxy-5 ␤ -hydroxy-B-norcholestane-6 ␤ -carboxaldehyde (secosterol-B) were recently detected in human atherosclerotic tissues and brain specimens, and they may play pivotal roles in the pathogenesis of atherosclerosis and neurodegenerative diseases. However, as their origin remains unidentifi ed, we examined the formation mechanism, the stability, and the fate of secosterols in vitro and in vivo. About 40% of secosterol-A remained unchanged after 3 h incubation in the FBS-free medium, whereas 20% and 40% were converted to its aldehyde-oxidation product, 3 ␤ -hydroxy-5-oxo-secocholestan-6-oic acid, and secosterol-B, respectively. In the presence of FBS, almost all secosterol-A was converted immediately to these compounds. Secosterol-B in the medium, with and without FBS, was relatively stable, but ‫ف‬ 30% was converted to its aldehyde-oxidation product, 3 ␤ -hydroxy-5 ␤ -hydroxy-B-norcholestane-6-oic acid (secoB-COOH). When neutrophillike differentiated human leukemia HL-60 (nHL-60) cells activated with PMA were cultured in the FBS-free medium containing cholesterol, signifi cantly increased levels of secosterol-A and its aldehyde-oxidation product, but not secosterol-B, were formed. This secosterol-A formation was decreased in the culture of PMA-activated nHL-60 cells containing several reactive oxygen species (ROS) inhibitors and scavengers or in the culture of PMA-activated neutrophils isolated from myeloperoxidase (MPO)-defi cient mice. Our results demonst...

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Section: Analysis Of Secosterols By Lc-ms/msmentioning

confidence: 99%

Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway

Tomono

Miyoshi

Shiokawa

et al. 2011

Journal of Lipid Research

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“…Therefore carboxylic acids are sometimes transformed to the hydrophobic and ionizable structures. Higashi et al reported the simple and practical method for the analysis of carboxylic acids using 2-hydrazinopyridine (HP) (53) and 2-picolylamine (PA) (54). Several biological important compounds having carboxylic acids, such as chenodeoxycholic acid, were derivatized with these reagents at 60ºC for 10 min in the presence of the condensation reagents.…”

Section: Carboxylic Acidsmentioning

confidence: 99%

“…The derivatization followed by LC/ESI-MS/MS enabled the detection of trace amount of the clinically important carboxylic acids such as bile acids, homovanillic acid in human saliva. The detection responses of PA-derivatives were increased by 9-158 folds over the intact carboxylic acids (54). Similarly (60,61) were used for the derivatization of carboxylic acids.…”

Section: Carboxylic Acidsmentioning

confidence: 99%

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Derivatization in liquid chromatography for mass spectrometric detection

Santa¹

2013

Drug Discov Ther

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“…To improve the MS response, carboxylic acids are frequently derivatized prior to analysis. Various derivatization reagents including chiral derivatization reagents for the MS response have been steadily developed for the labeling of carboxyl group [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Quantitative Analysis of Ketoprofen Enantiomers by Liquid Chromatography/Electrospray Ionization-Mass Spectrometry

Yang¹,

Jin²

2017

Proceedings of the 2016 International Conference on Biological Engineering and Pharmacy (BEP 2016)

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Abstract-A enantioselective and sensitive liquid chromatography/ electrospray ionization-mass spectrometry (LC/ESI-MS) method is developed for the quantitative analysis of ketoprofen (KET) enantiomers based on a straightforward one-pot two-step stable isotope-coded derivatization of KET with a chiral derivatization reagent, (S)-1-methyl-4-(5-(3-aminopyrrolidin-1-yl)-2,4-dinitrophenyl)piperazine, and methyl iodide, respectively. The processes introduce not only a chiral tagging to the analytes but also a quaternary amine to the analytes, making the analytes permanently charged. The OPTSICD enabled the highly sensitive detection and complete separation of the KET enantiomers. By using second derivatization step with methyl iodide-d 3 (CD 3 I), a complete set of deuterated standards was utilized and used as internal standards. The use of deuterated KET-derivatives significantly improved the assay precision and accuracy. The developed method was successfully applied to the quantitative analysis of KET in human saliva.

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Simple and practical derivatization procedure for enhanced detection of carboxylic acids in liquid chromatography–electrospray ionization-tandem mass spectrometry

Cited by 108 publications

References 21 publications

Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway

Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway

Derivatization in liquid chromatography for mass spectrometric detection

Quantitative Analysis of Ketoprofen Enantiomers by Liquid Chromatography/Electrospray Ionization-Mass Spectrometry

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