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A Comprehensive LC/MS Analysis of Novel Cyclopentenedione Library.
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SYSNO ASEP 0466008 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title A Comprehensive LC/MS Analysis of Novel Cyclopentenedione Library. Author(s) Papoušková, B. (CZ)
Bernard, Martin (UCHP-M) SAI
Ottenschlager, Jakub (UCHP-M)
Karban, Jindřich (UCHP-M) RID, ORCID, SAI
Velíšek, Petr (UCHP-M) RID, SAI
Hrbáč, J. (CZ)
Sýkora, Jan (UCHP-M) RID, ORCID, SAI
Storch, Jan (UCHP-M) RID, ORCID, SAI
Vacek, J. (CZ)Source Title Journal of Pharmaceutical and Biomedical Analysis. - : Elsevier - ISSN 0731-7085
Roč. 128, SEP 5 (2016), s. 342-351Number of pages 10 s. Language eng - English Country NL - Netherlands Keywords bioactive cyclopentenediones ; liquid chromatography ; mass spectrometry Subject RIV CF - Physical ; Theoretical Chemistry Institutional support UCHP-M - RVO:67985858 UT WOS 000381591900041 EID SCOPUS 84974668342 DOI 10.1016/j.jpba.2016.05.048 Annotation Here we focused on the design and synthesis of a library of novelized benzylidene CPD derivatives that were consequently characterized by ultra-high performance liquid chromatography (UHPLC) on-line connected with tandem mass spectrometry (MS/MS). The library design was based on a 2-benzylidene-4-cyclopentene-1,3-dione skeleton substituted with a variety of hydroxy, methoxy, halogen, linear aliphatic, heterocyclic and saccharide moieties, primarily modulating the skeleton's hydrophobicity. The prepared CPDs were effectively ionized by positive/negative atmospheric pressure photoionization (APPI) and atmospheric pressure chemical ionization (APCI). After careful optimization of the dopant composition and flow rate, positive-mode APPI proved to be more sensitive than APCI. In negative mode, both ionization techniques gave similar results. Further, a detailed MS fragmentation study was performed, confirming the structure of the compounds and enabling positional isomers of CPDs to be differentiated on the basis of their collision spectra analysis. Finally, an optimization of the composition of the mobile phase and reversed-phased separation mode were done, followed by a selection of the most suitable UHPLC stationary phases, i.e. C-18, C-8 and phenyl. The applicability of the method was evaluated by the inclusion of the other two substances in the study, i.e. monomeric and dimeric bioactive CPDs, compound TX-1123 and nostotrebin 6 with cytostatic and antimicrobial activities, respectively. The results presented here could be used in further investigations of the chromatographic retention and MS behavior of CPDs, which could be utilized for their isolation, detailed characterization and analysis in biological systems. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2017
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