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Ca2+ Selective Host Rotaxane Is Highly Toxic Against Prostate Cancer Cells

David B Smithrud1, Lucas Powers1, Jennifer Lunn1

  • 1Contribution from the Department of Chemistry, University of Cincinnati , Cincinnati, Ohio 45221, United States.

ACS Medicinal Chemistry Letters
|February 16, 2017
PubMed

Insights

New rotaxanes show promise for treating prostate cancer. A novel crown ether rotaxane (CEHR2) selectively binds calcium ions (Ca2+), enhancing toxicity against cancer cells, offering a potential new therapy for advanced prostate cancer.

Area of Science:

  • Supramolecular Chemistry
  • Oncology
  • Materials Science

Background:

  • Androgen-resistant prostate cancer requires novel therapeutic strategies.
  • Prostate cancer often metastasizes to bone, a calcium-rich environment.
  • Existing ionophores for metal cation delivery are too toxic for clinical use.

Purpose of the Study:

  • To design and synthesize a novel rotaxane capable of selective calcium ion (Ca2+) binding.
  • To evaluate the efficacy of the synthesized rotaxane in delivering Ca2+ into cancer cells.
  • To assess the therapeutic potential of Ca2+-binding rotaxanes against prostate cancer cell lines.

Main Methods:

  • Synthesis of a new rotaxane, CEHR2, featuring a benzyl 15-crown-5 ether for Ca2+ binding.
  • Investigated cation transfer selectivity of CEHR2 using aqueous solutions and chloroform.
  • Assessed the cytotoxicity of CEHR2 and a control rotaxane (CEHR1) against human prostate cancer cell lines (PC-3, 22Rv1, C4-2).

Main Results:

  • CEHR2 demonstrated efficient transfer of Ca2+ over alkali metal cations and Mg2+.
  • CEHR2 exhibited superior Ca2+ transfer capabilities compared to CEHR1 (containing an 18-crown-6 ether).
  • CEHR2 showed significantly enhanced toxicity against PC-3, 22Rv1, and C4-2 prostate cancer cells compared to CEHR1.

Conclusions:

  • Crown ether rotaxanes can be rationally designed for selective metal cation binding.
  • Targeted Ca2+ association via rotaxanes can lead to enhanced cytotoxicity.
  • This approach offers a promising strategy for developing new therapies for androgen-resistant prostate cancer.
Keywords:
Prostate cancercalciumcrown ethersrotaxanes

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