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Transition Metal Chemistry

, Volume 44, Issue 6, pp 575–583 | Cite as

Synthesis, characterization and anti-tumor activity of Pd(II) complexes with 4,5-benzo-3H-1,2-dithiole-3-thione

  • Subhi A. Al-JiboriEmail author
  • Mustafa A. Ulghafoor
  • Ahmet KaradağEmail author
  • Ali Aydın
  • Hüseyin Akbaş
  • Santiago G. Ruiz
Article
  • 83 Downloads

Abstract

Reaction of Na2[PdCl4] with two equivalents of 4,5-benzo-3H-1,2-dithiole-3-thione (btt) affords cis-[PdCl21-btt)2] (1), which provides a convenient entry into mixed-ligand btt complexes. Addition of one equivalent of a range of diamines or diphosphines gives the salts [Pd(κ1-btt)22-diamine)]Cl2 (2ad) (diamine = en, dap, bipy, phen) and [Pd(btt)22-diphosphine)]Cl2 (3ac) (diphosphine = dppe, dppp, dppf) in good yields. In contrast, two equivalents of dppm result in [Pd(κ1-btt)21-dppm)2]Cl2 (4), where the diphosphine binds in a monodentate fashion. Two equivalents of PPh3 result in a mixture of cis- and trans-isomers of [Pd(κ1-btt)2(PPh3)2]Cl2 (5ab) (ca. 1:5 ratio); the pure trans-isomer 5b was isolated by ion-exchange chromatography. The cis-isomer 5a could be synthesized independently from the reaction of cis-[PdCl2(PPh3)2] with two equivalents of btt. In all of these complexes, the btt ligand binds in a monodentate manner through the exocyclic thione sulfur. The anti-tumor activities of representative examples, cis-[PdCl21-btt)2] (1), cis-[Pd(κ1-btt)21-dppm)2]Cl2 (4) and cis-[Pd(κ1-btt)2(PPh3)2] (5a), were evaluated by cell proliferation assays and phase-contrast microscopy against prostate cancer cell lines PC3, DU145 and LNCaP, with complexes 1 and 4 showing potent anti-proliferative effects (TGI values of 19.2 and 21.1 µg/mL, respectively) against LnCaP cells.

Graphical abstract

Notes

Acknowledgements

We thank Tikrit University, Iraq, and Tokat Gaziosmanpaşa University, Turkey, for their supports.

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Copyright information

© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.Chemistry Department, College of ScienceTikrit UniversityTikrītIraq
  2. 2.Biotechnology Department, College of ScienceBartin UniversityBartinTurkey
  3. 3.Chemistry Department, College of Arts ScienceTokat Gaziosmanpaşa UniversityTokatTurkey
  4. 4.Tuzla State Hospital, Central LaboratoryMinistry of HealthIstanbulTurkey
  5. 5.Departamento de Biología y Geología, Física y Química Inorgánica, ESCETUniversidad Rey Juan CarlosMóstoles, MadridSpain

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