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Selective LC-MS/MS method for the identification of BMAA from its isomers in biological samples
Stockholm University, Faculty of Science, Department of Analytical Chemistry.
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2012 (English)In: Analytical and Bioanalytical Chemistry, ISSN 1618-2642, E-ISSN 1618-2650, Vol. 403, no 6, 1719-1730 p.Article in journal (Refereed) Published
Abstract [en]

Algal blooms are well-known sources of acute toxic agents that can be lethal to aquatic organisms. However, one such toxin, beta--methylamino--alanine (BMAA) is also believed to cause amyotrophic lateral sclerosis, also known as Lou Gehrig's disease. The detection and identification of BMAA in natural samples were challenging until the recent introduction of reliable methods. However, the issue of potential interference from unknown isomers of BMAA present in samples has not yet been thoroughly investigated. Based on a systematic database search, we generated a list of all theoretical BMAA structural isomers, which was subsequently narrowed down to seven possible interfering compounds for further consideration. The seven possible candidates satisfied the requirements of chemical stability and also shared important structural domains with BMAA. Two of the candidates, 2,4-diaminobutyric acid (DAB) and -(2-aminoethyl) glycine (AEG) have recently been studied in the context of BMAA. A further isomer, beta-amino--methyl-alanine (BAMA), has to be considered because it can potentially yield the fragment ion, which is diagnostic for BMAA. Here, we report the synthesis and analysis of BAMA, together with AEG, DAB, and other isomers that are of interest in the separation and detection of BMAA in biological samples by using either high-performance liquid chromatography or ultra-high-performance liquid chromatography coupled with tandem mass spectrometry. We detected for the first time BAMA in blue mussel and oyster samples. This work extends the previously developed liquid chromatography-tandem mass spectrometry platform Spacil et al. (Analyst 135:127, 2010) to allow BMAA isomers to be distinguished, improving the detection and identification of this important amino acid.

Place, publisher, year, edition, pages
2012. Vol. 403, no 6, 1719-1730 p.
Keyword [en]
ALS, Cyanobacteria, beta-amino-N-methylalanine (BAMA), AEG, DAB
National Category
Analytical Chemistry
Research subject
Analytical Chemistry
Identifiers
URN: urn:nbn:se:su:diva-79872DOI: 10.1007/s00216-012-5966-yISI: 000304166500023OAI: oai:DiVA.org:su-79872DiVA: diva2:551915
Note

AuthorCount:5;

Available from: 2012-09-12 Created: 2012-09-11 Last updated: 2017-12-07Bibliographically approved
In thesis
1. Mass Spectrometry of Non-protein Amino Acids: BMAA and Neurodegenerative Diseases
Open this publication in new window or tab >>Mass Spectrometry of Non-protein Amino Acids: BMAA and Neurodegenerative Diseases
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Neurodegenerative diseases have been shown to correlate positively with an ageing population. The most common neurodegenerative diseases are amyotrophic lateral sclerosis (ALS), Parkinson’s disease and Alzheimer’s disease. The cause of these diseases is believed to be the interaction between genetic and environmental factors, synergistically acting with ageing. BMAA (β-methylamino-L-alanine) is one kind of toxin present in our environment and might play an important role in the development of those diseases.

BMAA was initially isolated from cycad seeds in Guam, where the incidence of ALS/Parkinsonism-dementia complex among the indigenous people was 50 – 100 times higher than the rest of the world in the 1950’s. BMAA can induce toxic effects on rodents and primates. Furthermore, it can potentiate neuronal injury on cell cultures at concentrations as low as 10 µM. BMAA was reported to be produced by cyanobacteria, and could bio-magnify through the food chain.

In this thesis, work was initially focused on the improvement of an existing analytical method for BMAA identification and quantification using liquid chromatography coupled with tandem mass spectrometry.  Subsequently, the refined method was applied to environmental samples for probing alternative BMAA producer(s) in nature and to seafood samples for estimation of human exposure to this toxin.

In Paper I, a systematic screening of the isomers of BMAA in a database was performed and seven potential isomers were suggested. Three of them were detected or suspected in natural samples. In Paper II, a deuterated internal standard was synthesized and used for quantifying BMAA in cyanobacteria. In Paper III, Diatoms were discovered to be a BMAA producer in nature. In Paper IV, ten popular species of seafood sold in Swedish markets were screened for BMAA. Half of them were found to contain BMAA at a level of 0.01 – 0.90 µg/g wet weight. In Future perspectives, the remaining questions important in this field are raised.

Place, publisher, year, edition, pages
Stockholm: Department of Environmental Science and Analytical Chemistry, Stockholm University, 2015. 43 p.
Keyword
Neurodegenerative diseases, BMAA, Isomers, LC-MS/MS, Cyanobacteria, Diatoms, Seafood contamination
National Category
Analytical Chemistry
Research subject
Analytical Chemistry
Identifiers
urn:nbn:se:su:diva-114110 (URN)978-91-7649-028-0 (ISBN)
Public defence
2015-04-09, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrheniusväg 16 B, Stockholm, 10:00 (English)
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Available from: 2015-03-18 Created: 2015-02-20 Last updated: 2015-03-20Bibliographically approved

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