Self-Assembly of Ambidentate Pyridyl-Carboxylate Ligands with Octahedral Ruthenium Metal Centers: Self-Selection for a Single-Linkage Isomer and Anticancer-Potency Studies
- Authors
- Jung, Hyunji; Dubey, Abhishek; Koo, Hyun Jung; Vajpayee, Vaishali; Cook, Timothy R.; Kim, Hyunuk; Kang, Se Chan; Stang, Peter J.; Chi, Ki-Whan
- Issue Date
- May-2013
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- ambidentate ligands; anticancer agents; metallacycles; ruthenium; self-assembly
- Citation
- CHEMISTRY-A EUROPEAN JOURNAL, v.19, no.21, pp.6709 - 6717
- Journal Title
- CHEMISTRY-A EUROPEAN JOURNAL
- Volume
- 19
- Number
- 21
- Start Page
- 6709
- End Page
- 6717
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/14591
- DOI
- 10.1002/chem.201204371
- ISSN
- 0947-6539
- Abstract
- 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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