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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
Author(s) -
Jung Hyunji,
Dubey Abhishek,
Koo Hyun Jung,
Vajpayee Vaishali,
Cook Timothy R.,
Kim Hyunuk,
Kang Se Chan,
Stang Peter J.,
Chi KiWhan
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201204371
Subject(s) - carboxylate , ruthenium , chemistry , octahedron , moiety , stereochemistry , crystallography , metal , single crystal , octahedral molecular geometry , crystal structure , catalysis , organic chemistry
Abstract The synthesis of six new [2+2] metallarectangles through the coordination‐driven self‐assembly of octahedral Ru II ‐based acceptors with ambidentate pyridyl‐carboxylate donors is described. These molecular rectangles are fully characterized by 1 H NMR 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 1 H NMR 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 ( 9 – 11 ) were particularly high against AGS cancer cells, with IC 50 values that were comparable to that of reference drug cisplatin.