Anticancer Potency and Multidrug-Resistant Studies of Self-Assembled Arene-Ruthenium Metallarectangles
- Authors
- Dubey, Abhishek; Min, Jin Wook; Koo, Hyun Jung; Kim, Hyunuk; Cook, Timothy R.; Kang, Se Chan; Stang, Peter J.; Chi, Ki-Whan
- Issue Date
- 26-Aug-2013
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- antitumor agents; cancer; metallarectangles; multidrug resistance; ruthenium; self-assembly
- Citation
- CHEMISTRY-A EUROPEAN JOURNAL, v.19, no.35, pp.11622 - 11628
- Journal Title
- CHEMISTRY-A EUROPEAN JOURNAL
- Volume
- 19
- Number
- 35
- Start Page
- 11622
- End Page
- 11628
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/14371
- DOI
- 10.1002/chem.201300870
- ISSN
- 0947-6539
- Abstract
- A suite of three tetraruthenium metallacycles have been obtained from [2+2] self-assemblies between N,N'-Di-(4-pyridyl)-1,4,5,8-naphthalenetetracarbo-xydiimide (4) and one of the three dinuclear arene ruthenium clips, (eta(6)-p-iPrC(6)H(4)Me)(2)Ru-2(OO boolean AND OO)][OTf](2) (OO boolean AND OO=oxalate 1, 2,5-dioxydo-1,4-benzoquinonato (dobq) 2, 5,8-dihydroxy-1,4-naphthaquinonato (donq) 3; OTf=triflate). All complexes were isolated in good yield (>85%) as triflate salts and were fully characterized by using (HNMR)-H-1 and UV/Vis spectroscopies, and high-resolution electrospray mass spectrometry. A single crystal of the metallarectangle 5 was suitable for X-ray diffraction structural characterization. The biological activities of the metallacycles were determined by using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assays, establishing their in vitro anticancer properties. Our results show that for the AGC (gastric cancer) cell lines, the cytotoxicity of (donq)-containing SCC 7 exceeds that of cisplatin, which was used as a control. For HCT15 (colon cancer) cell lines, the cytotoxicity is comparable to both cisplatin and doxorubicin. An in vivo hollow fiber model was used to show growth-inhibitory activity against HCT15 and image-based cytometry experiments indicated that 7 induced apoptosis as the mode of cell death. Complex 7 also showed significant antitumor activity for multidrug-resistant HCT15/CLO2 cell lines, for which doxorubicin was ineffective.
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