Introduction: A
fragmentation pathway of atorvastatin de-protonated ion was proposed based on
rational interpretation workflows. Method: The
mass spectral data (MS, MS/MS and MS3) of atorvastatin was obtained
by electrospray negative ionization mode with flow injection analysis; using
liquid chromatography systems coupled with tandem mass spectrometers (Q-trap
and Q-ToF). Results: The
fragmentation pathway was established using fragment ions of de-protonated ion;
elemental composition, molecular structure and mechanism of formation for each
major fragment presented. Pathway was proposed based on the MS3 spectral data in combination with basic interpretation rules and rational
workflows. Conclusion: This
study and data interpretation workflows can be useful for writing fragmentation
pathway, mechanism for formation of fragments, and can be applied for mass
spectral data interpretation of similar small organic molecules.
Cite this paper
Shandilya, D. K. , Israni, R. and Joseph, P. E. (2018). Prediction of the Fragmentation Pathway of Atorvastatin De-Protonated Ion. Open Access Library Journal, 5, e4547. doi: http://dx.doi.org/10.4236/oalib.1104547.
Aksenov, A.A., da Silva, R., Knight, R., Lopes, N.P. and Dorrestein, P.C. (2017) Global Chemical Analysis of Biology by Mass Spectrometry: Nature Reviews Chemistry. Nature Reviews Chemistry, 1, Article No. 0054.
Pramanik, B.N., Bartner, P.L. and Chen, G. (1999) The Role of Mass Spectrometry in the Drug Discovery Process. Current Opinion in Drug Discovery & Development, 2, 401-417.
Nicolas, C.E. and Schoolz, T.H. (1998) Active Drug Substances Impurity Profiling Part II. LC-MS/MS Fin-gerprinting. Journal of Pharmaceutical and Biomedical Analysis, 16, 825-836. https://doi.org/10.1016/S0731-7085(97)00132-5
Cooks, R.G., Chen, G., Wong, P. and Wollnik, H. (1997) Mass Spectrometers. In: Trigg, G.L., Ed., Encyclopedia of Applied Physics, Vol. 19, VCH Publishers, New York, 289.
Chen, G., Pramanik, B.N., Liu, Y.-H. and Mirza, U.A. (2007) Applications of LC/MS in Structure Identifications of Small Molecules and Proteins in Drug Discovery. Journal of Mass Spectrometry, 42, 279-287. https://doi.org/10.1002/jms.1184
Ermer, J. (1998) The Use of Hyphenated LC-MS Technique for Characterization of Impurity Profiles during Drug Development. Journal of Pharmaceutical and Biomedical Analysis, 18, 707-714. https://doi.org/10.1016/S0731-7085(98)00267-2
Angelika, G., Harrison, M.W., Herniman, J.M., Skylaris, C.-K. and Langely, G.J. (2013) A Predictive Science Approach to Aid Understanding of Electrospray Ionization Trandem Mass Spectrometric Fragmentation Pathway of Small Molecules Using Density Fuctional Calculations. Rapid Communications in Mass Spectrometry, 27, 964-970. https://doi.org/10.1002/rcm.6536
Holcapek, M., Jirasko, R. and Lísa, M. (2010) Basic Rules for the Interpretation of Atmospheric Pressure Ionization Mass Spectra of Small Molecules. Chromatography A, 1217, 3908-3921. https://doi.org/10.1016/j.chroma.2010.02.049
Johnson, A.R. and Carlson, E.E. (2015) Collision-Induced Dissociation Mass Spectrometry: A Powerful Tool for Natural Product Structure Elucidation. ACS Publications Analytical Chemistry, 87, 10668-10678. https://doi.org/10.1021/acs.analchem.5b01543
Guan, F.Y., Soma, L.R. and Luo, Y. (2006) Collision-Induced Dissociation Pathways of Anabolic Steroids by Electrospray Ionization Tandem Mass Spectrometry. Journal American Society of Mass Spectrometry, 17, 477-489. https://doi.org/10.1016/j.jasms.2005.11.021
Dermarque, D.P., Crotti, A.E.M., Vessecchi, R., Lopes, J.L.C. and Lopes, N.P. (2016) Fragmentation Reactions Using Electrospray Ionization Mass Spectrometry: and Important Tool for Structural Elucidation and Characterization of Synthetic and Natural Products. Natural Product Reports, 33, 432. https://doi.org/10.1039/C5NP00073D
Shandilya, D.K., Joseph, P.E. and Kantamreddi, V.S.S. (2017) Prediction of the Fragmentation Pathway of Atorvastatin by Using High Resolution Collision Induced Dissociation (HR-MS/MS) Spectral Data. Open Access Library Journal, 4, e3473. https://doi.org/10.4236/oalib.1103473
Shandilya, D.K., Joseph, P.E. and Kantamreddi, V.S.S. (2017) Interpretation of Full Scan Atmospheric Pressure Ionization Mass Spectra (MS) and Collision Induced Dissociation Fragmentation Spectra (MS/MS) of Small Organic Molecules—A Mini Review. Systematic Reviews in Pharmacy, 8, 23-25.
