Simultaneous Metabolite Identification and Quantitation with UV Data Integration Using LightSight Software Version 2.2

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1 Technical ote Simultaneous Metabolite Identification and Quantitation with UV Data Integration Using LightSight Software Version 2.2 Alek. Dooley, Carmai Seto, esham Ghobarah, and Elliott B. Jones verview: Integration of UV and MS data is highly desirable for biotransformation studies. For example, in vitro metabolic stability studies can provide qualitative metabolism data, as well as kinetics for the parent compound using the MS data. Relative quantitation of metabolites detected can also be performed and integration of UV data is very useful for this aspect of the workflow. Manual processing and correlation of both data streams is time consuming. ere, we show qualitative and quantitative data collected by acquiring both mass spectrometric and UV data in the same experiment, and then processing and correlating both data types automatically in LightSight software version 2.2. Introduction: Drug metabolism studies often require estimation of relative abundances of metabolites detected in addition to structure elucidation. While MS based detection is a powerful technique for detection and structure elucidation, small changes in the structure and functional groups present in a metabolite can often lead to major differences in ionization efficiency and fragmentation. Therefore, it is often difficult to estimate metabolite concentrations based on the MS signal in the absence of a reference standard for quantitation. By comparison, UV absorbance is considered to provide a more uniform response which allows for estimation of relative abundances of metabolites. Integration of MS and analog data processing is highly desirable as it allows the drug metabolism scientist to perform structure elucidation based on the MS/MS data, estimate concentration based on the UV data, and generate one integrated report. In this technical note, we describe the use of LightSight software version 2.2 to study the in vitro metabolism of bromocriptine using a QTRAP LC/MS/MS system in combination with integrated UV detection, data processing and reporting. Experimental Conditions: omocriptine was incubated at 50 μm in rabbit liver microsomes using an ADP regenerating system under oxidative conditions at 37 C. After 1 hour, the incubation was quenched with an equal volume of acetonitrile. The supernatant was then diluted 1:5 with water for injection. This gave a final concentration of 5 μm for bromocriptine in the T 0 control.

2 A 5μL volume of sample was injected onto a Phenomenex Polar-RP PLC column (2 x 50 mm, 4µm). The mobile phase consisted of water (A) and acetonitrile (B), each containing 0.1% formic acid. The gradient (Figure 1) was optimized to ensure sufficient separation of metabolites over a wide polarity range relative to the parent, which eluted at 60% B. Prior to the mass spectrometric analysis, the LC eluent was fed through a Shimadzu SDP20AV dual wavelength detector, set to 302 nm. Predictive multiple reaction monitoring with information dependant acquisition (pmrm-ida) methods were created using LightSight software v2.2 and run on a 4000 QTRAP hybrid triple Figure 1. LC Gradient used to analyze bromocriptine incubations. quadrupole linear ion trap mass spectrometer. With prior knowledge of the parent drug s MS/MS fragmentation, theoretical MRM transitions for metabolites can be generated based on a particular biotransformation set. The pmrm experiments were built using the Phase I comprehensive biotransformation set included in the LightSight software. A total of 166 MRM transitions were included in the pmrm survey scan linked to a single enhanced product ion (EPI) dependent scan. The EPI experiment was acquired at a scan rate of 4,000 Da/sec with dynamic fill time turned on. Structural elucidation and assignment of the MS/MS fragments was performed with the assistance of the ACD/Labs software package. Results and Discussion: Figure 2 shows the molecular structure of bromocriptine, with the sites of MS/MS fragmentation indicated along with the nominal mass of the fragment. The m/z 346 fragment ion was chosen as the Q3 mass for the pmrm method. Compounds with a higher lambda maximum (λ max ) above the typical background solvent absorbance at nm, will yield excellent data quality that correlates nicely with MRM data. Therefore bromocriptine which has a λ max of 302 nm was a suitable choice. If there is complementary analog data (PDA, UV, or ADC data such as β-ram) available, LightSight software will correlate the MS data with the analog data and vice versa. The potential metabolites table in the software reports metabolites from both data streams, providing for the integration of both data types as well as ensuring that any potential metabolite that is only detected in one data stream is still reported. Using the Figure 2. The MS/MS fragmentation of bromocriptine LightSight software, a total of 14 metabolites were detected and identified including 11 oxidative metabolites; a summary of the MS and UV data for these metabolites is shown in Table 1. Figure 3 shows the correlation between the MS data and the UV trace performed in the LightSight software

3 Figure 3. Correlation of UV and MS data in the Processing Workspace of LightSight software version 2.2. R.T. (min.) - Peak Area - % Area - Peak ID Biotransformation Mass Shift Expected m/z Q1 / Q3 R.T. (min) Peak Area % Area Peak eight Analog Analog Analog M1 Demethylation / E E+03 M2 Demethylation / E E+04 M3 Loss of / E E+04 M4 Tri-xidation / E E+03 M5 Di-xidation / E E E M6 Di-xidation + ydrogenation / E E E M7 Tri-xidation + ydrogenation / E E E M8 Di-xidation / E E E M9 xidation / E E E M11 xidation + ydrogenation / E E E M10 Di-xidation / E E E M12 xidation / E E E Parent / E E E M13 xidation / E E+04 M14 xidation / E E E+01 4 Parent / E E+03 Table 1. omocriptine metabolites identified using LightSight software sorted by retention time.

4 The metabolites included single, di-, and tri-oxidations of bromocriptine. The proposed structure of some of the metabolites is shown in Figure 4. Figure 5 shows the comparison between a tri-oxidation metabolite of bromocriptine and the parent MS/MS spectra. The pmrm transition that corresponds to the triple-oxidation metabolite shows 4 clear peaks in the MS chromatogram, and the UV trace further confirms that these peaks are potential metabolites (see Figure 6). 3 C R C R R =, 2 or 3 R =, 2 or 3 M9, M12, M13, M14: xidation M4: Tri-xidation M5, M6, M8, M10: Di-xidation M11: xidation + ydrogenation M6: Di-xidation + ydrogenation M7: Tri-xidation + ydrogenation Figure 4. Proposed structures for metabolites of bromocriptine detected in the microsomal incubation.. C C +MSMS of (Di-xidation) Intensity, cps Intensity, cps 1.0e6 8.0e5 6.0e5 4.0e5 2.0e5 0.0e0 +MSMS of (Parent) 1.5e5 1.0e5 5.0e4 0.0e C m/z, Da m/z, Da C + C C Figure 5. The comparison between bromocriptine (bottom panel) and a di-oxidation metabolite reveals that all the fragments at or below m/z are common between both spectra Therefore, the sites of metabolism do not occur on these portions of the parent drug.

5 Figure 6. The selected ion chromatogram for the di-oxidation metabolites of bromocriptine (top) and the UV chromatogram (bottom). Conclusions: LightSight software version 2.2 efficiently identifies, confirms, and quantitates metabolites using both MS and analog data. Identification and structure elucidation based on the MS and MS/MS data, and relative quantitation based on UV were both performed in a singe integrated workspace.. For Research Use nly. ot for use in diagnostic procedures. The trademarks mentioned herein are the property of either Life Technologies Corporation, Applied Biosystems/MDS Analytical Technologies or otherwise, their respective owners Applied Biosystems LLC and MDS Inc. Joint wners. All rights reserved. eadquarters 850 Lincoln Centre Drive Foster City, CA USA Phone Toll Free International Sales For our office locations please call the division headquarters or refer to our Website at

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