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KMID : 0385520110240020078
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Analytical Science & Technology
2011 Volume.24 No. 2 p.78 ~ p.84
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Electrospray ionization tandem mass fragmentation pattern of camostat and its degradation product, 4-(4-guanidinobenzoyloxy)phenylacetic acid
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Kwon Soon-Ho
Shin Hye-Jin
Park Ji-Myeong
Lee Kyoung-Ryul
Kim Young-Jin
Lee Sang-Hoo
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Abstract
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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 CO₂ and HN=C=NH from the parent ion at m/z 312.
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KEYWORD
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camostat, 4-(4-guanidinobenzoyloxy)phenylacetic acid, serine protease inhibitor, ESI-MS/MS, CID
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