Synthesis, structure and cytotoxic activity of trans-[PtCl2(EugH)(Caffeine)] and [PtCl(Eug)(Caffeine)] (EugH: eugenol) complexes

Truong Thuy Hang; Le Thi Duyen; Nguyen Thi Thanh Chi

doi:10.51316/jca.2021.031

Authors

Truong Thuy Hang Faculty of Chemistry, Hanoi National University of Education Author
Le Thi Duyen Hanoi University of Mining and Geology, Duc Thang, Bac Tu Liem, Ha Noi Author
Nguyen Thi Thanh Chi Faculty of Chemistry, Hanoi National University of Education Author

DOI:

https://doi.org/10.51316/jca.2021.031

Keywords:

Caffeine, Eugenol, Platinum(II), complexes

Abstract

Interaction between K[PtCl₃(EugH)] (1) and [PtCl(Eug)]₂ (2) with Caf afforded two new complexes, trans-[PtCl₂(EugH)(Caf)] (3) and [PtCl(Eug)(Caf)] (4), respectively. The procedure to synthesize complex 2 was improved. The structures of two new complexes were characterized by elemental analyses, MS, IR, ¹H NMR and NOESY spectroscopies. The result indicated that EugH coordinates with Pt(II) at ethylenic double bond of the allyl group in complex 3, but in complex 4 it is deprotonated and bound with Pt(II) at both the double bond and C5 of the benzene ring. The donor N of caffein is in trans-position in 3 and in cis-position in 4 with respect to the ethylenic double bond. In chloroform solvent, 4 exists in two forms 4a and 4b corresponding to the strong intermolecular hydrogen bond Cl₃C-H…ClPt(II) and the strong halogen bond Cl₂HC-Cl…Pt(II). The result of testing cytotoxicity of 3 and 4 against four human cancer cells KB, Lu, Hep-G2 and MCF7 showed that complex 3 exhibits good activities on the KB and Hep-G2 with IC₅₀ values of 81,03 and 89,29 μg/mL, respectively.

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