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- Title
Structural elucidation of a new sildenafil analogue using high-resolution Orbitrap mass spectrometry.
- Authors
Kee, Chee‐Leong; Ge, Xiaowei; Low, Min‐Yong; Koh, Hwee‐Ling
- 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.
- Publication
Rapid Communications in Mass Spectrometry: RCM, 2013, Vol 27, Issue 12, p1380
- ISSN
0951-4198
- Publication type
Article
- DOI
10.1002/rcm.6590