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Synthesis, characterization and biological evaluation of Pd(II), Cu(II) Re(I) and 99mTc(I) thiazole-based complexes

Abstract

A new thiazole-containing multidentate ligand 2-((2-phenyl-thiazol-4-yl)methylthio)-ethaneamine, L was synthesized and used to prepare new complexes of the formula PdIILCl2 (Pd-L), CuIIL2Cl2 (Cu-L) and fac-[Re/99mTcI(CO)3(L)]+ (Re/99mTc-L). The ligand L and the metal complexes were characterized spectroscopically. Furthermore, the structure of Re-L and Cu-L was elucidated by X ray crystallography. Ligand L acts as a bidentate (Nth, S) chelator in Pd-L, as a bidentate (N, S) chelator in Cu-L and as a tridentate (Nth, S, N) chelator in Re-L. The radiotracer 99mTc-L was synthesized in high yield and characterised by HPLC comparison with the Re-L analog. The synthesized compounds were evaluated for their anti-inflammatory and cytotoxic properties. The compounds exhibit low anti-inflammatory activity with Pd-L showing the higher activity among them. The cytotoxic activity of the ligand and the complexes against several human cancer cell lines: cervix adenocarcinoma HeLa, colorectal adenocarcinoma LS-174T, lung adenocarcinoma A549, breast adenocarcinoma MDA-MB-231 and normal human lung fibroblast cell line MRC-5, was examined using the MTT assay. The complex Cu-L exhibited the highest cytotoxicity and the complex Pd-L showed the best tumor selectivity. The changes in the cell cycle phase distribution were determined by flow cytometry and it was found that ligand L shows the highest apoptotic activity. The biodistribution studies of 99mTc-L in mice showed fast tissue clearance. Of all the thiazole-containing compounds, the palladium complex appears to be more promising for future efforts.

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Publication details

The article was received on 05 Feb 2018, accepted on 11 Apr 2018 and first published on 13 Apr 2018


Article type: Research Article
DOI: 10.1039/C8MD00067K
Citation: Med. Chem. Commun., 2018, Accepted Manuscript
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    Synthesis, characterization and biological evaluation of Pd(II), Cu(II) Re(I) and 99mTc(I) thiazole-based complexes

    J. Mašković, A. Hatzidimitriou, A. Damjanovic, T. Stanojkovic, S. R. Trifunovic, A. Geronikaki and D. Papagiannopoulou, Med. Chem. Commun., 2018, Accepted Manuscript , DOI: 10.1039/C8MD00067K

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