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Self-Assembly of Ambidentate Pyridyl-Carboxylate Ligands with Octahedral Ruthenium Metal Centers: Self-Selection for a Single-Linkage Isomer and Anticancer-Potency Studies

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 21, Pages 6709-6717

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201204371

Keywords

ambidentate ligands; anticancer agents; metallacycles; ruthenium; self-assembly

Funding

  1. World Class University program [R33-2008-000-10003]
  2. Priority Research Center program through the National Research Foundation of Korea [2009-0093818]
  3. U.S. National Institutes of Health [GM-057052]

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The synthesis of six new [2+2] metallarectangles through the coordination-driven self-assembly of octahedral RuII-based acceptors with ambidentate pyridyl-carboxylate donors is described. These molecular rectangles are fully characterized by 1HNMR spectroscopy, high-resolution electrospray mass spectrometry, and single-crystal X-ray diffraction. In each case, despite the possible formation of multiple isomers, based on the relative orientation of the pyridyl and carboxylate groups (head-to-head versus head-to-tail), evidence for the formation of a single preferred ensemble (head-to-tail) was found in the 1HNMR spectra. Furthermore, the cytotoxicities of all of the rectangles were established against A549 (lung), AGS (gastric), HCT-15 (colon), and SK hep 1 (liver) human cancer cell lines. The cytotoxicities of rectangles that contained the 5,8-dihydroxy-1,4-naphthaquinonato bridging moiety between the Ru centers (911) were particularly high against AGS cancer cells, with IC50 values that were comparable to that of reference drug cisplatin.

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