2-Hydrazinoquinoline: A Reactive Matrix for Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry to Detect Gaseous Carbonyl Compounds

Abstract

The sensitivity, range of applications, and reaction mechanism of 2-hydrazinoquinoline as a reactive matrix for matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) were examined. Using a reaction chamber (125 L) equipped with a stirring fan and a window for moving the MALDI-MS plate and volatile samples in and out, the sensitivities of 2-hydrazinoquinoline to gaseous aldehydes (formaldehyde, acetaldehyde, propionaldehyde, and n-butyraldehyde) and ketones (acetone, methyl ethyl ketone, and methyl isobutyl ketone) were determined to be at least parts per million (ppm) levels. On the other hand, carboxylic acids (formic acid, acetic acid, propionic acid, and butyric acid) and esters (ethyl acetate, pentyl acetate, isoamyl acetate, and methyl salicylate) could not be detected by 2-hydrazinoquinoline in MALDI-MS. In addition to 2,4-dinitrophenylhydrazine, a common derivatization reagent for analyzing carbonyl compounds quantitatively in gas chromatography and liquid chromatography, the dissolution of 2-hydrazinoquinoline in an acidic solution, such as trifluoroacetic acid, was essential for its function as a reactive matrix for MALDI-MS.

Keywords

aldehyde hydrazide hydrazine 2-hydrazinoquinoline ketone MALDI-MS reactive matrix

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References

Tanaka

Waki

Ido

Akita

Yoshida

, “Protein and polymer analyses up to m/z 100000 by laser ionization time-of flight mass spectrometry”, Rapid Commun. Mass Spectrom. 2, 151 (1988). doi: https://dx-doi-org.web.bisu.edu.cn/10.1002/rcm.1290020802

Dreisewerd

, “The desorption process in MALDI”, Chem. Rev. 103, 395 (2003). doi: https://dx-doi-org.web.bisu.edu.cn/10.1021/cr010375i

Dreisewerd

, “Recent methodological advances in MALDI”, Anal. Bioanal. Chem. 406, 2261 (2014). doi: https://dx-doi-org.web.bisu.edu.cn/10.1007/s00216-014-7646-6

Hillenkamp

Peter-Katalinic

, MALDI MS. A Practical Guide to Instrumentation, Methods and Applications, 2nd edn. Wiley-Blackwell, Weinheim (2013).

Shigeri

Yasuda

Sakai

Ikeda

Sato

Kinumi

, “Hydrazide and hydrazine reagents as reactive matrices for MALDI-MS to detect steroids”, Eur. J. Mass Spectrom. 21, 79 (2015). doi: https://dx-doi-org.web.bisu.edu.cn/10.1255/ejms.1336

Takigawa

Saijo

Morimoto

Nakayama

Shibata

Tanaka

Yoshimura

Chikara

Kishi

, “A longitudinal study of aldehydes and volatile organic compounds associated with subjective symptoms related to sick building syndrome in new dwellings in Japan”, Sci. Total Environ. 61, 417 (2012). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.scitotenv.2011.12.060

Shigeri

Ikeda

Yasuda

Ando

Sato

Kinumi

, “Hydrazide and hydrazine reagents as reactive matrices for MALDI-MS to detect gaseous aldehydes”, J. Mass Spectrom. 49, 742 (2014). doi: https://dx-doi-org.web.bisu.edu.cn/10.1002/jms.3408

Brombacher

Owen

Volmer

, “Automated coupling of capillary-HPLC to matrix-assisted laser desorption/ionization mass spectrometry for the analysis of small molecules utilizing a reactive matrix”, Anal. Bioanal. Chem. 376, 773 (2003). doi: https://dx-doi-org.web.bisu.edu.cn/10.1007/s00216-003-2024-9

Mugo

Bottaro

, “Rapid on-plate and one-pot derivatization of carbonyl compounds for enhanced detection by reactive matrix LDI-TOF MS using the tailor -made reactive matrix, 4-dimethylamino-6-(4-methoxy-1-naphthyl)-1,3,5-triazine-2-hydrazine (DMNTH)”, J. Mass Spectrom. 42, 206 (2007). doi: https://dx-doi-org.web.bisu.edu.cn/10.1002/jms.1153

10.

Mugo

Bottaro

, “Rapid analysis of alpha-dicarbonyl compounds by laser desorption/ionization mass spectrometry using 9-(3,4-diaminophenyl)acridine (DAA) as a reactive matrix”, Rapid Commun. Mass Spectrom. 22, 1087 (2008). doi: https://dx-doi-org.web.bisu.edu.cn/10.1002/rcm.3450

11.

Monopoli

Calvano

Nacci

Palmisano

, “Boronic acid chemistry in MALDI MS: A step forward in designing a reactive matrix with molecular recognition capabilities”, Chem. Commun. 50, 4322 (2014). doi: https://dx-doi-org.web.bisu.edu.cn/10.1039/c4cc01185f

12.

Flinders

Morrell

Marshall

Ranshaw

Clench

, “The use of hydrazine-based derivatization reagents for improved sensitivity and detection of carbonyl containing compounds using MALDI-MSI”, Anal. Bioanal. Chem. 407, 2085 (2015). doi: https://dx-doi-org.web.bisu.edu.cn/10.1007/s00216-014-8223-8

13.

Shariatgorji

Nilsson

Kallback

Karlsson

Zhang

Svenningsson

Andren

, “Pyrylium salts as reactive matrices for MALDI-MS imaging of biologically active primary amines”, J. Am. Soc. Mass Spectrom. 26, 934 (2015). doi: https://dx-doi-org.web.bisu.edu.cn/10.1007/s13361-015-1119-9

14.

Zaikin

Borisov

Polovkov

Slyundina

, “Reactive matrices for matrix-assisted laser desorption/ionization mass spectrometry of primary amines”, Eur. J. Mass Spectrom. 21, 403 (2015). doi: https://dx-doi-org.web.bisu.edu.cn/10.1255/ejms.1353

15.

Suh

Eltanawy

Rangan

Saba

, “A facile stable-isotope dilution method for determination of sphingosine phosphate lyase activity”, Chem. Phys. Lipids, 194, 101 (2016). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.chemphyslip.2015.09.006

16.

Yao

Chen

, “2-hydrazinoquinoline as a derivatization agent for LC-MS-based metabolomics investigation of diabetic ketoacidosis”, Metabolites 3, 993 (2013). doi: https://dx-doi-org.web.bisu.edu.cn/10.3390/metabo3040993

17.

Uchiyama

Inaba

Kunugita

, “Derivatization of carbonyl compounds with 2,4-dinitrophenylhy-drazine and their subsequent determination by high-performance liquid chromatography”, J. Chromatogr. B 879, 1282 (2011). doi: https://dx-doi-org.web.bisu.edu.cn/10.1016/j.jchromb.2010.09.028

18.

http://www.waters.com/waters/partDetail.htm?partNumber=WAT037500.