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Title: Structural elucidation of a new sildenafil analogue using high-resolution Orbitrap mass spectrometry
Authors: Kee, C.-L.
Ge, X.
Low, M.-Y.
Koh, H.-L. 
Issue Date: 30-Jun-2013
Citation: Kee, C.-L., Ge, X., Low, M.-Y., Koh, H.-L. (2013-06-30). Structural elucidation of a new sildenafil analogue using high-resolution Orbitrap mass spectrometry. Rapid Communications in Mass Spectrometry 27 (12) : 1380-1384. ScholarBank@NUS Repository.
Abstract: RATIONALE One new phosphodiesterase type 5 (PDE-V) inhibitor, propoxyphenyl homohydroxysildenafil (PP-HHS), has been isolated from one health supplement, and analyzed using high-resolution Orbitrap mass spectrometry. High-resolution mass spectrometry (HRMS) is useful to elucidate unknown substances at low concentrations. METHODS Two isolated compounds, propoxyphenyl thiohomohydroxysildenafil (PP-THHS) and propoxyphenyl homohydroxysildenafil (PP-HHS), were infused into the Thermo Fischer Scientific LTQ Orbitrap XL™ hybrid FTMS system at a flow rate of 3 μL per min. The high-resolution MS2 spectra were acquired using different high-energy collision dissolution (HCD) mode; 40 V for PPT-HHS and 45 V for PP-HHS. The accurate mass measurement was assisted with the aid of Mass Frontier software, version 5.0. RESULTS The fragmentation pattern of PP-HHS in the MS2 spectrum is very similar to that of PP-THHS except the product ions at m/z 519, 501, 325, 299 and 283 are less than PP-THHS by 16 m/z units. This is a result of the replacement of sulfur atom by oxygen at the thiolactam moiety. All the mass errors are below 5.0 ppm. CONCLUSIONS High-resolution Orbitrap mass spectrometry is an alternative method to determine unknown compounds like PDE-V inhibitor analogues unambiguously by analyzing the product ions at high mass accuracy. PP-HHS is an unapproved drug and no pharmacological study has been reported. Hence, it could be harmful to unknowing consumers with undesirable side effects. Copyright © 2013 John Wiley & Sons, Ltd. Copyright © 2013 John Wiley & Sons, Ltd.
Source Title: Rapid Communications in Mass Spectrometry
ISSN: 09514198
DOI: 10.1002/rcm.6590
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