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Use of Perfluorinated Phosphines to Provide Thermomorphic Anticancer Complexes for Heat-Based Tumor Targeting

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Anna K. Renfrew, Rosario Scopelliti and Paul J. Dyson*

Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), CH-1015 Lausanne, Switzerland

Inorg. Chem., 2010, 49 (5), pp 2239–2246

DOI: 10.1021/ic9020433

Publication Date (Web): February 4, 2010

*To whom correspondence should be addressed. E-mail: paul.dyson@epfl.ch.

Section:

Organometallic and Organometalloidal Compounds

Abstract

A series of compounds of general formula [Ru(η⁶-arene)(pta)(PR₃)Cl]BF₄ (arene = p-cymene or 4-phenyl-2-butanol; pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane, PR₃ = PPh₂(p-C₆H₄C₂H₄C₈F₁₇), PPh(p-C₆H₄C₂H₄C₈F₁₇)₂, P(p-C₆H₄C₂H₄C₆F₁₃)₃, PPh₃ or P(p-C₆H₄F)₃) have been prepared and characterized by spectroscopic methods. The structure of [Ru(η⁶-p-cymene)(pta)Cl(P(p-C₆H₄F)₃)]BF₄ has also been established in the solid state by X-ray crystallography. The cytotoxicities of the compounds were determined in the A2780 and A2780 cisplatin-resistant cell lines revealing that the fluorinated phosphines significantly increase antiproliferative activity relative to their bis-chloride precursors. Two of the complexes were found to be thermoresponsive, that is, showing poor water solubility at 37 °C and good solubility at 42 °C, the temperature of a heated tumor, providing a method of tumor targeting. Incubation at 42 °C for 2 h resulted in improved cytotoxicities for two of the complexes.

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Synthesis, Characterization, and Photophysical Properties of Three Platinum(II) Complexes Bearing Fluorescent Analogues of the Di-2-pyridylmethane Ligand
Justin J. Wilson, Juliana Fedoce Lopes and Stephen J. Lippard
Inorganic Chemistry2010 49 (11), 5303-5315
- Synthesis, Characterization, and Photophysical Properties of Three Platinum(II) Complexes Bearing Fluorescent Analogues of the Di-2-pyridylmethane Ligand
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  Inorganic Chemistry2010 49 (11), 5303-5315
  Three new ligands of the general formula [RNHCH(py)2] (py = pyridine; R = tosyl, Ts-dpm; R = dansyl, Ds-dpm; R = 7-nitro-1,2,3-benzoxadiazole, NBD-dpm) have been synthesized and characterized. Reactions of these ligands with cis-[Pt(DMSO)2Cl2] (DMSO = ...
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