Pyrylium Salts as Reactive Matrices for MALDI-MS Imaging of Biologically Active Primary Amines

Many neuroactive substances, including endogenous biomolecules, environmental compounds, and pharmaceuticals possess primary amine functional groups. Among these are catecholamine neurotransmitters (e.g., dopamine), many substituted phenethylamines (e.g., amphetamine), as well as amino acids and neuropeptides. In most cases, mass spectrometric (ESI and MALDI) analyses of trace amounts of such compounds are challenging because of their poor ionization properties. We present a method for chemical derivatization of primary amines by reaction with pyrylium salts that facilitates their detection by MALDI-MS and enables the imaging of primary amines in brain tissue sections. A screen of pyrylium salts revealed that the 2,4-diphenyl-pyranylium ion efficiently derivatizes primary amines and can be used as a reactive MALDI-MS matrix that induces both derivatization and desorption. MALDI-MS imaging with such matrix was used to map the localization of dopamine and amphetamine in brain tissue sections and to quantitatively map the distribution of the neurotoxin beta-N-methylamino-L-alanine.

MEDICIN OCH HÄLSOVETENSKAP Medicinska och farmaceutiska grundvetenskaper Farmaceutiska vetenskaper hsv//swe
MEDICAL AND HEALTH SCIENCES Basic Medicine Pharmaceutical Sciences hsv//eng
MALDI matrix
Mass spectrometry imaging
Neurotransmitter
Catecholamine
Phenethylamine
Amphetamine
Primary amine
Reactive matrix
Neurotoxin

Nilsson, Anna (author)
Kallback, Patrik (author)
Karlsson, OskarKarolinska Institutet,Uppsala universitet,Institutionen för farmaceutisk biovetenskap(Swepub:uu)oskar255 (author)
Zhang, XiaoqunKarolinska Institutet (author)
Svenningsson, PerKarolinska Institutet (author)
Andren, Per E. (author)
Uppsala universitetInstitutionen för farmaceutisk biovetenskap (creator_code:org_t)

In:Journal of the American Society for Mass Spectrometry: American Chemical Society (ACS)26:6, s. 934-9391044-03051879-1123

By the author/editor: Shariatgorji, Mo ...; Nilsson, Anna; Kallback, Patrik; Karlsson, Oskar; Zhang, Xiaoqun; Svenningsson, Pe ...; show more...; Andren, Per E.; show less...

About the subject

MEDICAL AND HEALTH SCIENCES: MEDICAL AND HEAL ...; and Basic Medicine; and Pharmaceutical S ...

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