Structure elucidation of a novel analog of sildenafil detected as an adulterant in a dietary supplement using LC-UV and LC/MS.

A sildenafil-related compound was detected in a dietary supplement marketed as an aphrodisiac. The compound was detected during analysis of the dietary supplement using LC-UV and LC/electrospray ionization-MS. The structure of the compound was established using high resolution MS, NMR spectrometry, and X-ray crystal structure analysis. The compound was identified as 5-(5-((3,5-dimethylpiperazin-1-yl)sulfonyl)-2-ethoxyphenyl)-l-methyl-7-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-3-propyl-1H-pyrazolo[4,3-d] pyrimidine. Based on this structure, the compound was named nitroprodenafil. The dietary supplement was found to contain 90 mg nitroprodenafil/capsule. This article describes the structural characterization of a new sildenafil-related compound. The compound was detected during analysis of a dietary supplement using LC-UV and LC/electrospray ionization (ESI)-MS. The structure was established using high resolution MS (HRMS), NMR spectrometry, and X-ray crystal structure analysis. The structures of methisosildenafil, thiomethisosildenafil, and this new analog, named nitroprodenafil (21), are shown in Figure 1. In the Demizu et al. report, the compound is named mutaprodenafil instead ofnitroprodenafil. Considering the naming right, the authors of this paper think the use of mutaprodenafil is appropriate as the compound name, although nitroprodenafil is used.

Differentiation between sulfoaildenafil and its analogs.

An analog of aildenafil, which is a potent and highly selective inhibitor of phosphodiesterase 5, was found in a dietary supplement marketed for enhancement of sexual function. The compound was isolated by silica gel column chromatography, and its structure was identified by means of 13C-NMR spectrometry, 1H-NMR spectrometry, high-resolution MS, and X-ray structure determination. The compound was identified to be sulfoaildenafil (other names: thioaildenafil, dimethyl sildenafil thione, and thiomethisosildenafil). Sulfoaildenafil is very similar to the compound thiohomosildenafil. As it is difficult to distinguish between them by LC-photodiode array detector analysis, ultra-performance LC (UPLC)/MS, ion trap LC/MS/MS (LC/IT-MS/MS), and GC/MS were performed. The mass spectra of thiohomosildenafil by UPLC/MS and LC/IT-MS/MS showed mass fragments of m/z 58, 72, and 355, and the mass spectrum by GC/MS showed mass fragments of m/z 56, 72, and 420. Some of these fragments had low intensities, but they were useful for distinguishing between the two compounds. The relationship between aildenafil (other names: dimethylsildenafil and methisosildenafil) and homosildenafil is similar to that between sulfoaildenafil and thiohomosildenafil. Therefore, these compounds were also examined.

Development of an electrochemical antifouling system for seawater cooling pipelines of power plants using titanium.

Biofouling is the undesirable adhesion and development of microorganisms and macroorganisms in a water environment. An electrochemical antifouling system based on management of primary adhesion of microorganisms was developed employing titanium electrode for antifouling of seawater cooling pipes and marine infrastructures. The system consists of an electrochemical reaction-monitoring unit, a power control unit, and a potential/current remote monitoring and a control unit. Titanium plates and iron plates were used as the working and counter electrode, respectively. Field experiment was conducted in the seawater cooling pipeline system of a thermal power station. Four titanium electrodes with 1.0 m length and 3.0 m width were set in the seawater intake pit and current density was controlled at 50-100 mA/m(2). The electrode surface maintained clean conditions for 2 years. The average wet weight of fouling organisms on the titanium electrode surface was below 100 g/m(2) whereas the corresponding wet weight was above 10 kg/m(2) on the control surface. Using titanium as the electrode material, chlorine and hypochlorite are not generated. The developed electrochemical antifouling system provided an effective, environmentally friendly, and feasible techniques for remote operations.