Abstract
The mass spectra behaviour of five 10-alkylthiocolchicine derivatives has been studied using electron ionization and MALDI-TOF MS techniques. Fragmentation patterns of colchicines derivatives after EI have been investigated, as well as mass spectra after collision-induced dissociation (CID) MALDI have been used to gain structural information. To the best of our knowledge, this is the first time that the MALDI MS/MS data for colchicine and its alkylthio derivatives have been described. It has been shown also that the data derived from mass spectra can be used for identification/quantitative determination of natural and modified alkaloids of colchicine group. The detailed fragmentation pathways proposed here could be helpful for the characterization of other colchicines of these type. The utility of different ionization techniques for analysis of compounds of this class has been evaluated. Due to the cytotoxic activity towards tumour cell lines, 10-alkylthiocolchicines may be considered as the active ingredients of anticancer agents. If these compounds find use in medical treatment, their distribution in organism and their metabolism will have to be monitored by spectroscopic or spectrometric methods. The characteristic fragment ions may be used by Selected Reaction Monitoring method for determination of colchicine analogues.
Highlights
Colchicine is an alkaloid occurring in plants of Liliaceae family especially in meadow saffron Colchicum autumnale and Gloriosa superba and it is best known for its antimitotic effects.[1,2,3] The extract from the plants containing this compound has been well known for ages as a medicine against gout as first described in De Materia Medica by Pedanius Dioscorides.[4]
As a part of the investigation, aiming at the differentiation of isomeric derivatives of 10-alkylthiocolchicines on the basis of the values of the coefficients μ, i.e. the abundances of selected even or odd-electron fragment ions relative to the abundances of the corresponding molecular ions, we reported here a detailed analysis of the electron ionization (EI) mass spectra of compounds 1–5
In this report we examined a series of colchicine derivatives, i.e. 10-alkylthiocolchicines 1–5, which have been obtained as model compounds of changed geometry in comparison with colchicine itself
Summary
Colchicine is an alkaloid occurring in plants of Liliaceae family especially in meadow saffron Colchicum autumnale and Gloriosa superba and it is best known for its antimitotic effects.[1,2,3] The extract from the plants containing this compound has been well known for ages as a medicine against gout as first described in De Materia Medica by Pedanius Dioscorides.[4]. Introducing alkylthio groups of different length to the colchicine molecule alters its shape, and influences its complexing ability due to the sulfur atom and changes electron density distribution in the molecule due to the electron-donating properties of the alkyl group. Distribution of the chemotherapeutic agents in the tissues of an organism can be monitored using MALDI imaging Taking into account these facts it appears very important to examine this class of potentially pharmacologically active compounds using the variety of mass spectral ionization techniques in order to learn their behavior under different mass spectral conditions and establish the fragmentation pattern of colchicine derivatives.
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