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On-Tissue Chemical Derivatization of Catecholamines Using 4-(N-Methyl)pyridinium Boronic Acid for ToF-SIMS and LDI-ToF Mass Spectrometry Imaging

Kaya, Ibrahim (author)
Gothenburg University,Göteborgs universitet,National Center for Imaging Mass Spectrometry,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,University of Gothenburg,Sahlgrenska universitetssjukhuset,Sahlgrenska University Hospital
Brülls, Steffen, 1991 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Dunevall, Johan (author)
Gothenburg University,Göteborgs universitet,National Center for Imaging Mass Spectrometry,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,University of Gothenburg
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Jennische, Eva, 1949 (author)
Gothenburg University,Göteborgs universitet,Institutionen för biomedicin,Institute of Biomedicine,University of Gothenburg
Lange, Stefan, 1948 (author)
Gothenburg University,Göteborgs universitet,Institutionen för biomedicin,Institute of Biomedicine,University of Gothenburg
Mårtensson, Jerker, 1965 (author)
Chalmers tekniska högskola,Chalmers University of Technology
Ewing, Andrew G, 1957 (author)
Gothenburg University,Göteborgs universitet,Institutionen för kemi och molekylärbiologi,National Center for Imaging Mass Spectrometry,Department of Chemistry and Molecular Biology,University of Gothenburg
Malmberg, Per, 1974 (author)
Gothenburg University,Göteborgs universitet,National Center for Imaging Mass Spectrometry,University of Gothenburg,Chalmers tekniska högskola,Chalmers University of Technology
Fletcher, John S. (author)
Gothenburg University,Göteborgs universitet,National Center for Imaging Mass Spectrometry,Institutionen för kemi och molekylärbiologi,Department of Chemistry and Molecular Biology,University of Gothenburg
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 (creator_code:org_t)
2018-10-22
2018
English.
In: Analytical Chemistry. - : American Chemical Society (ACS). - 0003-2700 .- 1520-6882. ; 90:22, s. 13580-13590
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  • Journal article (peer-reviewed)
Abstract Subject headings
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  • The analysis of small polar compounds with ToF-SIMS and MALDI-ToF-MS have been generally hindered by low detection sensitivity, poor ionization efficiency, ion suppression, analyte in-source fragmentation, and background spectral interferences from either a MALDI matrix and/or endogenous tissue components. Chemical derivatization has been a well-established strategy for improved mass spectrometric detection of many small molecular weight endogenous compounds in tissues. Here, we present a devised strategy to selectively derivatize and sensitively detect catecholamines with both secondary ion ejection and laser desorption ionization strategies, which are used in many imaging mass spectrometry (IMS) experiments. Chemical derivatization of catecholamines was performed by a reaction with a synthesized permanent pyridinium-cation-containing boronic acid molecule, 4-(N-methyl)pyridinium boronic acid, through boronate ester formation (boronic acid-diol reaction). The derivatization facilitates their sensitive detection with ToF-SIMS and LDI-ToF mass spectrometric techniques. 4-(N-Methyl)pyridinium boronic acid worked as a reactive matrix for catecholamines with LDI and improved the sensitivity of detection for both SIMS and LDI, while the isotopic abundances of the boron atom reflect a unique isotopic pattern for derivatized catecholamines in MS analysis. Finally, the devised strategy was applied, as a proof of concept, for on-tissue chemical derivatization and GCIB-ToF-SIMS (down to 3 μm per pixel spatial resolution) and LDI-ToF mass spectrometry imaging of dopamine, epinephrine, and norepinephrine in porcine adrenal gland tissue sections. MS/MS using collision-induced dissociation (CID)-ToF-ToF-SIMS was subsequently employed on the same tissue sections after SIMS and LDI mass spectrometry imaging experiments, which provided tandem MS information for the validation of the derivatized catecholamines in situ. This methodology can be a powerful approach for the selective and sensitive ionization/detection and spatial localization of diol-containing molecules such as aminols, vic-diols, saccharides, and glycans along with catecholamines in tissue sections with both SIMS and LDI/MALDI-MS techniques. © 2018 American Chemical Society.

Subject headings

NATURVETENSKAP  -- Kemi -- Analytisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Analytical Chemistry (hsv//eng)
NATURVETENSKAP  -- Fysik -- Atom- och molekylfysik och optik (hsv//swe)
NATURAL SCIENCES  -- Physical Sciences -- Atom and Molecular Physics and Optics (hsv//eng)
NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

Amines
Chemical detection
Drug products
Hormones
Ionization
Isotopes
Mass spectrometers
Molecules
Norepinephrine
Secondary ion mass spectrometry
Synthesis (chemical)
Tissue
Chemical derivatization
Collision induced dissociation
Detection sensitivity
Imaging mass spectrometry
Laser desorption ionization
Mass spectrometric detection
Spectral interference
Spectrometric techniques
Tissue engineering

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ref (subject category)
art (subject category)

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