MetWorks Metabolite Identification Software

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1 m a s s s p e c t r o m e t r y MetWorks Metabolite Identification Software Enabling Confident Analysis of Metabolism Data Part of Thermo Fisher Scientific

2 MetWorks Software for the Confident Analysis of Metabolism Data MetWorks with Mass Frontier software provides a simple and complete solution for identifying drug metabolites. MetWorks software automates and simplifies identification of Phase I and Phase II metabolites Automatically identify and generate ion chromatograms for all expected metabolites. Detect and identify unpredicted modifications with advanced data analysis tools: Further confirm potential metabolites using background subtraction based on UV or radiochromatogram data. Analyze sample and controls and utilize MS n spectra, retention time, and m/z to target putative metabolites Refine metabolite identification using Mass Defect Filtering of high mass accuracy data 2MetWorks Metabolite Identification Software Incorporate isotope pattern recognition of both natural and artificial isotopes Correlate MS/MS and MS 3 spectra with those from the parent drug to identify common product ions and mass shifts related to neutral losses

3 MetWorks Simplifies Data Visualization and Reporting MetWorks data analysis complements the Data Dependent and Dynamic Exclusion capabilities of all Thermo Scientific ion trap mass spectrometers for simultaneous determination of metabolic stability and structural identification. MetWorks provides capabilities for confident analysis of metabolism data Detecting Known Modifications Detecting Unpredicted Modifications Multiple Mass Defect Filter Automatic Isotope Pattern Recognition Spectral Correlation Tools for Metabolite Confirmation Confident Metabolite Identification Comprehensive Data Visualization and Reporting MetWorks software is compatible with all Thermo Scientific mass spectrometers capable of performing MS/MS and MS n fragmentation. In addition, MetWorks allows high resolution accurate mass data from the LTQ Orbitrap and LTQ FT instruments to be fully leveraged. 3

4 Detecting Known Modifications Automatic Identification of Expected Modifications Choose from an extensive list of Phase I and II modifications and create a custom list of single and combined expected modifications for the parent drug of interest. During data Convenient reporting software displays full scan and product ion mass spectra for each expected metabolite in order to verify predicted biotransformations. acquisition, the user has the option to specify a custom MS/MS list to target metabolites. During data processing, MetWorks software will automatically generate Extracted Ion Chromatograms (EIC) for each expected metabolite. 4MetWorks Metabolite Identification Software Expected Modifications View A custom list of expected modifications was used for the analysis of Loperamide data from the Thermo Scientific LTQ XL linear ion trap. Extracted ion chromatograms for unmetabolized Loperamide (m/z ) and its demethylated (m/z ) and hydroxylated (m/z ) metabolites are shown at the top of the figure above. The full scan mass spectra (left) and product ion spectra (MS/MS, right) for demethylated Loperamide are shown at the bottom of the figure.

5 Detecting Unpredicted Modifications Simplify Identification of Unknown Drug Metabolites MetWorks software provides the flexibility to filter data in order to identify low and high abundance peaks related to the parent drug. These masses may arise from metabolites which were not initially predicted or included in a targeted mass list. MetWorks provides a number of different software filters to help detect these components so that automated MS n fragmentation can be triggered and structural identification confirmed. Component Subtraction Using Controls Component subtraction can remove the effect of matrix or non-drug related interferences from the sample data and uncover unpredicted metabolites. A MetWorks algorithm compares components found in Sample and Control using composite MS n data in addition to full scan retention time (RT) and m/z values. Component Detection View Highlighting the components at RT 4.4 minutes in Sample (metabolized Loperamide) and Control (unmetabolized Loperamide) total ion chromatograms (top two panels) links the components to their composite MS n spectra (bottom panel). Since the RT (4.4 minutes), m/z (437.30) and product ion spectra (MS/MS) of these two components are identical in both Sample and Control, they were automatically labeled in red in the chromatograms and can be excluded from further analysis. Components unique to the sample are labeled in green and are shown in the panel labeled Potential Modifications. Data was obtained using the LTQ XL linear ion trap. Using these criteria, Components in the Sample and Control that are the same can automatically be excluded from further analysis, while components that are unique to the sample are automatically highlighted in green for easy visualization. These components are potential drug metabolites. If a Control data file is not available, another option is to perform the background subtraction using the solvent (not shown). 5

6 Multiple Mass Defect Filter Biotransformations cause predictable changes to the mass of the parent drug. Mass defects arise since molecular masses of metabolites are non-integer and deviate from nominal mass values. This results in small changes of the mass defect between the parent drug and its metabolites. The MetWorks Mass Defect removes a significant amount of background interference originating from the matrix and unmasks low abundance metabolite peaks. MetWorks software enables the use of a combination of up to six Mass Defect Filters, such that all the results are compiled into one chromatogram. 6MetWorks Metabolite Identification Software Filter takes advantage of the high mass accuracy data from the LTQ Orbitrap and LTQ FT Ultra and the known mass defects for different biotransformations. After data acquisition, a software filter removes ions with mass defects that are outside a userdefined mass defect window based on all possible modifications of the parent drug. Consequently, this process automatically The effect of using single and multiple Mass Defect Filters on visualizing Oxime metabolites in rat hepatocytes. Unfiltered, single Phase I, single Phase II and combined Phase I and Phase II filtered base peak chromatograms are shown. The parent drug Oxime is highlighted. Data was obtained using the LTQ Orbitrap hybrid mass spectrometer. Note: the y-axis intensity value is lower for Phase II MDF than the other chromatograms shown.

7 Automatic Isotope Pattern Recognition Drug candidates which contain elements such as bromine and chlorine have easily distinguishable isotope patterns which are not common in endogenous metabolites found in body fluids. Drugs can also be artificially labeled using stable isotopes including 13 C, 2 H, and 15 N. For metabolism studies, these unique isotope patterns can act as intrinsic or extrinsic signatures that can be used to efficiently detect drug metabolites. MetWorks software can filter full scan mass spectra based on the changes in mass and relative abundance of these isotopes and automatically display extracted ion chromatograms representing these isotope patterns that indicate potential metabolites. The top panel shows the EIC for an unexpected demethylated hydroxylated Loperamide metabolite at m/z identified by isotope pattern recognition, which includes a rearrangement and a modification. The bottom panel shows full scan MS of the metabolite indicating a distinct chlorine isotope pattern with a mass difference of two (highlighted in red) that was automatically recognized by MetWorks software and determined to be desmethyl-hydroxyl Loperamide. Data was obtained using the LTQ Orbitrap hybrid mass spectrometer. 7

8 MetWorks Metabolite Identification Software Spectral Correlation Spectral correlation analysis compares MS/MS or MS 3 spectra between the sample (metabolized drug) and a reference (typically parent drug). The MetWorks correlation algorithm searches for product ion spectral components that are the same in metabolized and unmetabolized drugs (common product ions) or different through a consistent mass shift that indicates a chemical modification such as an adduct. The related parent ions are automatically highlighted as metabolites of interest. Spectral Correlations View Chromatogram before (A) and after (B) spectral correlation indicates identification of an unpredicted dehydroxy rearrangement of Loperamide at RT of 4.04 minutes with m/z of The MS 3 spectra of (C) unmetabolized Loperamide (reference) and (D) the rearranged dehydroxy metabolite are shown with common product ions highlighted in blue. Data was obtained using the LTQ XL linear ion trap. 8

9 Tools for Metabolite Confirmation Component Subtraction Using UV and Radiometric Data UV spectra and radiographic analysis can generate information that is complementary to mass spectrometry data and may help confirm the peaks that are related to the parent drug. These traces can be displayed together with the total ion chromatogram for visual comparison. In addition, the information from one trace can be used to confirm components that are related to the parent drug. Components that are the same in Sample (metabolized Loperamide) and Control (unmetabolized Loperamide) and that have retention times that do not match peaks in the UV chromatogram are removed from the total ion chromatogram (Components remaining after control and UV subtraction). The remaining peaks are likely drug metabolites. 9

10 MetWorks Metabolite Identification Software Confident Metabolite Identification Once putative metabolites are identified, the location of the functional modification and the assignment of overall structure can be facilitated using Mass Frontier software. Chemical Structures representing the possible sites of modification can be created and fragmented in silico using general mechanistic fragmentation rules and the extensive Fragmentation Library that contains literature-based fragmentation schemes. The fragment ions generated using this approach can be directly compared to those acquired during LC-MS n analysis. Mass spectral peaks can be automatically annotated with their corresponding structures. Structural annotation of N-demethylated metabolite of Loperamide is shown. Once metabolite structure is confirmed using Mass Frontier s fragmentation schemes, product ion structures can be assigned to the mass spectral peaks. 10

11 Comprehensive Data Visualization and Reporting The MetWorks Report View can be customized to display the information about the parent drug and the set of identified metabolites. This may include elemental formula, type of modification, structure, retention time, m/z, associated chromatograms, a list of the most intense fragment ions, spectral tree (MS n information), and mass difference between parent and metabolite. The Report View can be used to create reports in Adobe PDF, Microsoft Word, and Microsoft Excel formats. MetWorks Report View The user can add structures for characterized components and save them with the results file. F1-F3 are the most abundant fragment or product ions from the MS n data. Delta denotes the difference between the masses of the parent and metabolized drug. 11

12 Laboratory Solutions Backed by Worldwide Service and Support Tap our expertise throughout the life of your instrument. Thermo Scientific Services extends its support throughout our worldwide network of highly trained and certified engineers who are experts in laboratory technologies and applications. Put our team of experts to work for you in a range of disciplines from system installation, training and technical support, to complete asset management and regulatory compliance consulting. Improve your productivity and lower the cost of instrument ownership through our product support services. Maximize uptime while eliminating the uncontrollable cost of unplanned maintenance and repairs. When it s time to enhance your system, we also offer certified parts and a range of accessories and consumables suited to your application. To learn more about our products and comprehensive service offerings, visit us at In addition to these offices, Thermo Fisher Scientific maintains a network of representative organizations throughout the world. Australia Austria Belgium Canada China Denmark France Germany India Italy Japan Latin America Netherlands South Africa Spain Sweden / Norway / Finland Switzerland UK USA Thermo Fisher Scientific, San Jose, CA USA is ISO Certified Thermo Fisher Scientific Inc. All rights reserved. Mass Frontier and Fragmentation Library are trademarks of HighChem, Ltd; Adobe is a registered trademark of Adobe Systems Incorporated; Microsoft is a registered trademark of Microsoft Corporation. All other trademarks are the property of Thermo Fisher Scientific Inc. and its subsidiaries. Specifications, terms and pricing are subject to change. Not all products are available in all countries. Please consult your local sales representative for details. BR62428_E 10/07S

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