Exploring Raloxifene-Based Metallodrugs: A Versatile Vector Combined with Platinum(II), Palladium(II) and Nickel(II) Dichlorides and Carborates against Triple-Negative Breast Cancer

ChemMedChem. 2024 Jul 15;19(14):e202400006. doi: 10.1002/cmdc.202400006. Epub 2024 Jun 5.

Abstract

Triple-negative breast cancer (TNBC) poses challenges in therapy due to the absence of target expression such as estrogen receptor (ER), progesterone receptor (PR), and human epidermal growth factor receptor 2 (HER2). Frequently, the treatment of TNBC involves the combination of several therapeutics. However, an enhanced therapeutic effect can be also achieved within a single molecule. The efficacy of raloxifene can be improved by designing a raloxifene-based hybrid drug bearing a 2,2'-bipyridine moiety (2). Integration of platinum(II), palladium(II), and nickel(II) complexes into this structure dramatically changed the cytotoxicity. The platinum(II) dichloride complex 3 did not demonstrate any activity, while palladium(II) and nickel(II) dichloride complexes 4 and 5 exhibited various cytotoxic behavior towards different types of hormone-receptor positive (HR+) cancer and TNBC cell lines. The replacement of the two chlorido ligands in 3-5 with a dicarbollide (carborate) ion [C2B9H11]2- resulted in reduced activity of compounds 6, 7, and 8. However, the palladacarborane complex 7 demonstrated higher selectivity towards TNBC. Furthermore, the mechanism of action was shifted from cytotoxic to explicitly cytostatic with detectable proliferation arrest and accelerated aging, characterized by senescence-associated phenotype of TNBC cells. This study provides valuable insights into the development of hybrid therapeutics against TNBC.

Keywords: TNBC; metallacarborane; metallodrugs; nickel; palladium; platinum; raloxifene; senescence.

MeSH terms

  • Antineoplastic Agents* / chemical synthesis
  • Antineoplastic Agents* / chemistry
  • Antineoplastic Agents* / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation* / drug effects
  • Coordination Complexes* / chemical synthesis
  • Coordination Complexes* / chemistry
  • Coordination Complexes* / pharmacology
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor*
  • Female
  • Humans
  • Molecular Structure
  • Nickel* / chemistry
  • Nickel* / pharmacology
  • Palladium* / chemistry
  • Palladium* / pharmacology
  • Platinum* / chemistry
  • Platinum* / pharmacology
  • Raloxifene Hydrochloride* / chemistry
  • Raloxifene Hydrochloride* / pharmacology
  • Structure-Activity Relationship
  • Triple Negative Breast Neoplasms* / drug therapy
  • Triple Negative Breast Neoplasms* / pathology

Substances

  • Palladium
  • Nickel
  • Antineoplastic Agents
  • Platinum
  • Coordination Complexes
  • Raloxifene Hydrochloride