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Effect of the orthoquinone moiety in 9,10-phenanthrenequinone on its ability to induce apoptosis in HCT-116 and HL-60 cells.

Abstract
9,10-Phenanthrenequinone (9,10-PQ) is one of the most abundant quinones among diesel exhaust particulates. Recent data have suggested that quinones induce apoptosis in immune, epithelial and tumor cells, leading to respirator illness; however, the mechanisms by which quinones induce apoptosis and the structure required for this remain unknown. We studied the antitumor activity of 9,10-PQ analogs against two human tumor cell lines, HCT-116 colon tumor cells and HL-60 promyelocytic leukemia cells. The loss of the cis-orthoquinone unit in 9,10-PQ abrogated its ability to induce apoptosis in the two tumor cell lines, and the LC50 values of these analogs were indicated over 10 μM. An analog of 9,10-PQ in which the biaryl unit had been deleted displayed a reduced ability to induce tumor cell apoptosis, while the analogs 1,10-phenanthroline-5,6-dione (9) and pyrene-4,5-dione (10), which also had modified biaryl units, exhibited increased tumor cell apoptotic activity. The cis-orthoquinone unit in 9,10-PQ was identified as essential for its ability to induce apoptosis in tumor cells, and its biaryl unit is also considered to influence orthoquinone-mediated apoptotic activity.
AuthorsNoriyuki Hatae, Jun Nakamura, Tetsuo Okujima, Minoru Ishikura, Takumi Abe, Satoshi Hibino, Tominari Choshi, Chiaki Okada, Hiroko Yamada, Hidemitsu Uno, Eiko Toyota
JournalBioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 23 Issue 16 Pg. 4637-40 (Aug 15 2013) ISSN: 1464-3405 [Electronic] England
PMID23816373 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2013 Elsevier Ltd. All rights reserved.
Chemical References
  • Antineoplastic Agents
  • Phenanthrenes
  • 9,10-phenanthrenequinone
Topics
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Apoptosis (drug effects)
  • HCT116 Cells
  • HL-60 Cells
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Neoplasms (drug therapy)
  • Phenanthrenes (chemical synthesis, chemistry, pharmacology)

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