TY - JOUR
T1 - Synthesis and evaluation of some steroidal oximes as cytotoxic agents
T2 - Structure/activity studies (II)
AU - Cui, Jianguo
AU - Fan, Lei
AU - Huang, Yanmin
AU - Xin, Yi
AU - Zhou, Aimin
N1 - Funding Information:
The authors acknowledge the financial support of the National Natural Science Foundation of China (no.: 20562001 ), the Natural Science Foundation of Guangxi Province (no.: 0832106 ) and the Foundation of Guangxi Education Bureau ( 200707M5172 ).
PY - 2009/11/4
Y1 - 2009/11/4
N2 - Hydroximinosteroids isolated from marine sponges display a variety of biological functions including cytotoxicity and anti-virus. In this study, we synthesized a series of hydroximinosteroid derivatives with a different functional group on the ring A or B and various side chains at position 17, and analyzed the cytotoxicity of these compounds against sk-Hep-1, H-292, PC-3 and Hey-1B cancer cells. Our results revealed that although a cholesterol-type side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship between the chemical structure and biological function.
AB - Hydroximinosteroids isolated from marine sponges display a variety of biological functions including cytotoxicity and anti-virus. In this study, we synthesized a series of hydroximinosteroid derivatives with a different functional group on the ring A or B and various side chains at position 17, and analyzed the cytotoxicity of these compounds against sk-Hep-1, H-292, PC-3 and Hey-1B cancer cells. Our results revealed that although a cholesterol-type side chain at position 17 is required for the biological activity of the compounds as we previously confirmed, elimination of the 4,5-double bond augmented the cytotoxic activity for the steroidal oximes. In addition, the presence of a hydroxy on 3- or 6-position of the steroidal nucleus resulted in a remarkable increase of cytotoxic activity. Our findings present more evidence showing the relationship between the chemical structure and biological function.
KW - Antiproliferative activity
KW - Cytotoxicity
KW - Steroidal oximes
KW - Synthesis
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U2 - 10.1016/j.steroids.2009.07.009
DO - 10.1016/j.steroids.2009.07.009
M3 - Article
C2 - 19647756
AN - SCOPUS:69949160120
VL - 74
SP - 989
EP - 995
JO - Steroids
JF - Steroids
SN - 0039-128X
IS - 12
ER -