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

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Abstract

Reaction of Na2[PdCl4] with two equivalents of 4,5-benzo-3H-1,2-dithiole-3-thione (btt) affords cis-[PdCl2(κ1-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)2(κ2-diamine)]Cl2 (2a–d) (diamine = en, dap, bipy, phen) and [Pd(btt)2(κ2-diphosphine)]Cl2 (3a–c) (diphosphine = dppe, dppp, dppf) in good yields. In contrast, two equivalents of dppm result in [Pd(κ1-btt)2(κ1-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 (5a–b) (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-[PdCl2(κ1-btt)2] (1), cis-[Pd(κ1-btt)2(κ1-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.

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Acknowledgements

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

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Authors and Affiliations

  1. Chemistry Department, College of Science, Tikrit University, Tikrīt, Iraq

    Subhi A. Al-Jibori & Mustafa A. Ulghafoor

  2. Biotechnology Department, College of Science, Bartin University, 74100, Bartin, Turkey

    Ahmet Karadağ

  3. Chemistry Department, College of Arts Science, Tokat Gaziosmanpaşa University, 60250, Tokat, Turkey

    Ahmet Karadağ & Hüseyin Akbaş

  4. Tuzla State Hospital, Central Laboratory, Ministry of Health, 34944, Istanbul, Turkey

    Ali Aydın

  5. Departamento de Biología y Geología, Física y Química Inorgánica, ESCET, Universidad Rey Juan Carlos, Calle Tulipán s/n, 28933, Móstoles, Madrid, Spain

    Santiago G. Ruiz

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  1. Subhi A. Al-Jibori
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  2. Mustafa A. Ulghafoor
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Correspondence to Subhi A. Al-Jibori or Ahmet Karadağ.

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Al-Jibori, S.A., Ulghafoor, M.A., Karadağ, A. et al. Synthesis, characterization and anti-tumor activity of Pd(II) complexes with 4,5-benzo-3H-1,2-dithiole-3-thione. Transit Met Chem 44, 575–583 (2019). https://doi.org/10.1007/s11243-019-00314-6

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