Studies on High-energy Collision-induced Dissociation of Endogenous Cannabinoids: 2-Arachidonoylglycerol and N-Arachidonoylethanolamide in FAB-Mass Spectrometry
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- KASAI Hiroko F.
- Faculty of Pharmaceutical Sciences, Hoshi University
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- TSUBUKI Masayoshi
- Faculty of Pharmaceutical Sciences, Hoshi University
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- HONDA Toshio
- Faculty of Pharmaceutical Sciences, Hoshi University
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Abstract
Analysis of 2-arachidonoylglycerol (2-AG) and N-arachidonoylethanolamide (anandamide) via alkali or alkaline earth metal-adduct high-energy collision-induced dissociation (CID) in fast-atom bombardment (FAB) ionization-mass spectrometry (MS) is described. The CID-MS/MS of the [2-AG+Li]+ or [2-AG+Na]+ ion undergoes charge-remote fragmentation (CRF), which is useful for the determination of the double-bond positions in the hydrocarbon chain, while the CID-MS/MS of the [2-AG-H+Cat]+ (Cat = Mg2+, Ca2+, Ba2+) ion provides an abundant fragment ion of the cationized arachidonic acid species, which is derived from cleaving the ester bond via a McLafferty-type rearrangement in addition to structurally informative CRF ions in small amounts. On the other hand, the CID-MS/MS spectra of anandamide cationized with both alkali metal (Li+ or Na+) and alkaline earth metal (Mg2+, Ca2+, or Ba2+) show CRF patterns: the spectra obtained in lithium or sodium adduct are more clearly visible than those in magnesium, calcium, or barium adduct. The McLafferty rearrangement is not observed with metal-adduct anandamide. The characteristics in each mass spectrum are useful for the detection of these endogenous ligands. m-Nitrobenzyl alcohol (m-NBA) is the most suitable matrix. A lithium-adduct [2-AG+Li]+ or [anandamide+Li]+ ion is observed to be the most abundant in each mass spectrum, since the affinity of lithium for m-NBA is lower than that for other matrices examined.
Journal
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- Analytical Sciences
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Analytical Sciences 22 (7), 921-930, 2006
The Japan Society for Analytical Chemistry
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Details 詳細情報について
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- CRID
- 1390282679232333952
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- NII Article ID
- 10017605039
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- NII Book ID
- AA10500785
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- ISSN
- 13482246
- 09106340
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- NDL BIB ID
- 7968130
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- PubMed
- 16837740
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- Text Lang
- en
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- Data Source
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
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- Abstract License Flag
- Disallowed