PMID- 20832917 OWN - NLM STAT- MEDLINE DCOM- 20110203 LR - 20101011 IS - 1768-3254 (Electronic) IS - 0223-5234 (Linking) VI - 45 IP - 11 DP - 2010 Nov TI - The preparation of bi-functional organophosphine oxides as potential antitumor agents. PG - 5527-30 LID - 10.1016/j.ejmech.2010.08.038 [doi] AB - Following our previously reported pyridinyl phosphine oxides as antitumor agents, we targeted the commercially available C(2)-axial chiral organophosphine ligand catalysts, such as 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) 1 and 2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine (P-Phos) 2 as a convenient source for producing organophosphine oxides as antitumor leads. Their corresponding chiral and racemic bi-phosphine oxides 3 and 4 can be obtained easily through a simple oxidation step with hydrogen peroxide, and their antitumor activities towards human hepatocellular carcinoma Hep3B cell line were reported. We found out that compound 3 shows stronger antitumor activity than that of 4, where axial chirality cannot improve their activity. Further athymic nude mice Hep3B xenograft model demonstrates the attractive in vivo antitumor potential of 3. CI - Copyright (c) 2010 Elsevier Masson SAS. All rights reserved. FAU - Lam, Kim-Hung AU - Lam KH AD - Department of Applied Biology and Chemical Technology, Hong Kong Polytechnic University, Hong Kong, China. bcjoelam@inet.polyu.edu.hk FAU - Chui, Chung-Hin AU - Chui CH FAU - Gambari, Roberto AU - Gambari R FAU - Wong, Raymond Siu-Ming AU - Wong RS FAU - Cheng, Gregory Yin-Ming AU - Cheng GY FAU - Lau, Fung-Yi AU - Lau FY FAU - Lai, Paul Bo-San AU - Lai PB FAU - Tong, See-Wai AU - Tong SW FAU - Chan, Kit-Wah AU - Chan KW FAU - Wong, Wai-Yeung AU - Wong WY FAU - Chan, Albert Sun-Chi AU - Chan AS FAU - Tang, Johnny Cheuk-On AU - Tang JC LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't DEP - 20100824 PL - France TA - Eur J Med Chem JT - European journal of medicinal chemistry JID - 0420510 RN - 0 (Antineoplastic Agents) RN - 0 (Organophosphorus Compounds) RN - 0 (Oxides) SB - IM MH - Antineoplastic Agents/*chemical synthesis/*pharmacology MH - Cell Line, Tumor MH - Humans MH - Magnetic Resonance Spectroscopy MH - Organophosphorus Compounds/*chemical synthesis/*pharmacology MH - Oxides/chemistry MH - Spectrometry, Mass, Electrospray Ionization EDAT- 2010/09/14 06:00 MHDA- 2011/02/04 06:00 CRDT- 2010/09/14 06:00 PHST- 2010/07/19 00:00 [received] PHST- 2010/08/03 00:00 [revised] PHST- 2010/08/13 00:00 [accepted] PHST- 2010/09/14 06:00 [entrez] PHST- 2010/09/14 06:00 [pubmed] PHST- 2011/02/04 06:00 [medline] AID - S0223-5234(10)00616-1 [pii] AID - 10.1016/j.ejmech.2010.08.038 [doi] PST - ppublish SO - Eur J Med Chem. 2010 Nov;45(11):5527-30. doi: 10.1016/j.ejmech.2010.08.038. Epub 2010 Aug 24.