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http://dx.doi.org/10.5806/AST.2011.24.2.078

Electrospray ionization tandem mass fragmentation pattern of camostat and its degradation product, 4-(4-guanidinobenzoyloxy)phenylacetic acid  

Kwon, Soon-Ho (Department of Bioanalysis, Seoul Medical Science Institute & Seoul Clinical Laboratories)
Shin, Hye-Jin (Department of Bioanalysis, Seoul Medical Science Institute & Seoul Clinical Laboratories)
Park, Ji-Myeong (Department of Bioanalysis, Seoul Medical Science Institute & Seoul Clinical Laboratories)
Lee, Kyoung-Ryul (Department of Bioanalysis, Seoul Medical Science Institute & Seoul Clinical Laboratories)
Kim, Young-Jin (Department of Bioanalysis, Seoul Medical Science Institute & Seoul Clinical Laboratories)
Lee, Sang-Hoo (Department of Bioanalysis, Seoul Medical Science Institute & Seoul Clinical Laboratories)
Publication Information
Analytical Science and Technology / v.24, no.2, 2011 , pp. 78-84 More about this Journal
Abstract
The fragmentation patterns of a serine protease inhibitor, camostat, and its degradation product, 4-(4-guanidinobenzoyloxy)phenylacetic acid (GBPA), were for the first time investigated by a triple quadrupole tandem mass spectrometry equipped with an electrospray source (ESI-MS/MS) in positive and/or negative ion mode under collision-induced dissociation (CID). The positive CID spectrum of camostat showed distinctly that the single bond (C-O) cleavage between carbonyl group and oxygen atom of the ester bonds of the compound favorably occurred and then the loss of N,N-dimethylcarbamoylmethyl group was more susceptible than that of guanidine moiety. In the positive ion CID spectrum of GBPA, the initial cleavage between the carbonyl group and oxygen atom of 4-guanidinobenzoyloxy group also occurred, yielding the most abundant fragment ion at m/z 145. On the other hand, the negative CID spectrum of GBPA characteristically showed the occurrence of the most abundant peak at m/z 226 resulting from the sequential neutral losses of $CO_2$ and HN=C=NH from the parent ion at m/z 312.
Keywords
camostat; 4-(4-guanidinobenzoyloxy)phenylacetic acid; serine protease inhibitor; ESI-MS/MS; CID;
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