Thermal Decomposition Path-Studied by the Simultaneous Thermogravimetry Coupled with Fourier Transform Infrared Spectroscopy and Quadrupole Mass Spectrometry-Of Imidazoline/Dimethyl Succinate Hybrids and Their Biological Characterization

Marta Worzakowska; Małgorzata Sztanke; Jolanta Rzymowska; Krzysztof Sztanke

doi:10.3390/ma16134638

Thermal Decomposition Path-Studied by the Simultaneous Thermogravimetry Coupled with Fourier Transform Infrared Spectroscopy and Quadrupole Mass Spectrometry-Of Imidazoline/Dimethyl Succinate Hybrids and Their Biological Characterization

Materials (Basel). 2023 Jun 27;16(13):4638. doi: 10.3390/ma16134638.

Authors

Marta Worzakowska¹, Małgorzata Sztanke², Jolanta Rzymowska³, Krzysztof Sztanke⁴

Affiliations

¹ Department of Polymer Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Skłodowska University in Lublin, 33 Gliniana Street, 20-614 Lublin, Poland.
² Department of Medical Chemistry, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland.
³ Department of Biology and Genetics, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland.
⁴ Laboratory of Bioorganic Compounds Synthesis and Analysis, Medical University of Lublin, 4A Chodźki Street, 20-093 Lublin, Poland.

Abstract

The thermal decomposition path of synthetically and pharmacologically useful hybrid materials was analyzed in inert and oxidizing conditions for the first time and presented in this article. All the imidazoline/dimethyl succinate hybrids (1-5) were studied using the simultaneous thermogravimetry (TG) coupled with Fourier transform infrared spectroscopy (FTIR) and quadrupole mass spectrometry (QMS). It was found that the tested compounds were thermally stable up to 200-208 °C (inert conditions) and up to 191-197 °C (oxidizing conditions). In both furnace atmospheres, their decomposition paths were multi-step processes. At least two major stages (inert conditions) and three major stages (oxidizing conditions) of their decomposition were observed. The first decomposition stage occurred between T_5% and 230-237 °C. It was connected with the breaking of one ester bond. This led to the emission of one methanol molecule and the formation of radicals capable of further radical reactions in both used atmospheres. At the second decomposition stage (T_max2) between 230-237 °C and 370 °C (inert conditions), or at about 360 °C (oxidizing conditions), the cleavage of the second ester bond and N-N and C-C bonds led to the emission of CH₃OH, HCN, N₂, and CO₂ and other radical fragments that reacted with each other to form clusters and large clusters. Heating the tested compounds to a temperature of about 490 °C resulted in the emission of NH₃, HCN, HNCO, aromatic amines, carbonyl fragments, and the residue (T_max2a) in both atmospheres. In oxidizing conditions, the oxidation of the formed residues (T_max3) was related to the production of CO₂, CO, and H₂O. These studies confirmed the same radical decomposition mechanism of the tested compounds both in inert and oxidizing conditions. The antitumor activities and toxicities to normal cells of the imidazoline/dimethyl succinate hybrids were also evaluated. As a result, the two hybrid materials (3 and 5) proved to be the most selective in biological studies, and therefore, they should be utilized in further, more extended in vivo investigations.

Keywords: antihemolytic activity; antitumor activity; decomposition course; imidazoline/dimethyl succinate hybrids; thermal behavior; toxicity to normal cells.

Grants and funding

This research received no external funding.