Antiproliferative activity of methylated analogues of E- and Z-resveratrol.
The stilbenoids E-resveratrol (E-3,5,4'-trihydroxystilbene, 1), E-3,5,4'-trimethoxystilbene (2), E-3,4,4'-trimethoxystilbene (3) and E-3,4'-dimethoxy-5-hydroxystilbene (4) were converted by photoisomerization to their corresponding Z-isomers 5-8. Compounds 1-8 were subjected to antiproliferative activity bioassays towards a set of four different human cancer cell lines, namely DU-145 (androgen not responsive human prostate tumor), LNCaP (androgen responsive human prostate tumor), M-14 (human melanoma) and KB (human mouth epidermoid carcinoma). The methylated analogues of 1 are more active than the natural lead in the majority of bioassays. The most active compound was Z-3,5,4'-trimethoxystilbene (6), which showed against DU-145 and LNCaP cells GI50 values close to those of the anticancer drug vinorelbine; 6 resulted more active than its E-isomer 2 towards DU-145, LNCaP and especially KB cell lines. A number of methylated Z-isomers displayed a higher activity than their E-isomers, but E-resveratrol (1) was more active than Z-resveratrol (5) towards all the tested cell lines.
Cardile
Venera
V
Dipartimento di Scienze Fisiologiche, Università di Catania, Viale A. Doria 6, I-95125 Catania, Italy.
Chillemi
Rosa
R
Lombardo
Laura
L
Sciuto
Sebastiano
S
Spatafora
Carmela
C
Tringali
Corrado
C
D000818:Animals; D002455:Cell Division / Q000187:drug effects*; D002470:Cell Survival / Q000187:drug effects*; D002855:Chromatography, Thin Layer; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008745:Methylation; D009374:Neoplasms, Experimental / Q000473:pathology*; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014747:Vinblastine / Q000031:analogs & derivatives / Q000494:pharmacology; D000077235:Vinorelbine
D013267:Stilbenes; D014747:Vinblastine; D000077185:Resveratrol; D000077235:Vinorelbine