TY - JOUR
T1 - The preparation of bi-functional organophosphine oxides as potential antitumor agents
AU - Lam, Kim Hung
AU - CHUI, Chung Hin
AU - Gambari, Roberto
AU - Wong, Raymond Siu Ming
AU - Cheng, Gregory Yin Ming
AU - Lau, Fung Yi
AU - Lai, Paul Bo San
AU - Tong, See Wai
AU - Chan, Kit Wah
AU - WONG, Wai Yeung
AU - Chan, Albert Sun Chi
AU - Tang, Johnny Cheuk On
N1 - Funding Information:
Dr. C.H. Chui would like to acknowledge the financial support from Institute of Textiles and Clothing, the Hong Kong Polytechnic University (1ZV-5L from ITC, HKPU). Dr. C.H. Chui is supported by the Assistant Professorship from ITC, HKPU, and Prof. R. Gambari is sponsored by AIRC (Italian Association for Cancer Research) . The authors wish to dedicate to Professor Albert Sun-Chi Chan on his occasion of his 60th birthday, and to acknowledge Areas of Excellence Scheme established under the University Grants Committee of the Hong Kong Special Administrative Region, P.R. China (Project No. AoEP-10/01)
PY - 2010/11
Y1 - 2010/11
N2 - Following our previously reported pyridinyl phosphine oxides as antitumor agents, we targeted the commercially available C2-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.
AB - Following our previously reported pyridinyl phosphine oxides as antitumor agents, we targeted the commercially available C2-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.
KW - Antitumor activity
KW - Bi-functional organophosphine oxides
KW - Hepatocellular carcinoma
UR - http://www.scopus.com/inward/record.url?scp=77957861164&partnerID=8YFLogxK
U2 - 10.1016/j.ejmech.2010.08.038
DO - 10.1016/j.ejmech.2010.08.038
M3 - Journal article
C2 - 20832917
AN - SCOPUS:77957861164
SN - 0223-5234
VL - 45
SP - 5527
EP - 5530
JO - European Journal of Medicinal Chemistry
JF - European Journal of Medicinal Chemistry
IS - 11
ER -