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Title: Synthesis and study of the cancer cell growth inhibitory properties of α-, γ-tocopheryl and γ-tocotrienyl 2-phenylselenyl succinates
Authors: Vraka, Panayiota S.
Rikkou, Maria P.
Drouza, Chryssoula 
Keywords: Apoptosis
Cancer cells
Enzyme activation
Human beings
Issue Date: 2006
Publisher: Elsevier
Source: Bioorganic and medicinal chemistry, 2006, volume 14, issue 8, pages 2684-2696
Abstract: Vitamin E succinate selenium-conjugated molecules were synthesized and their apoptogenic properties were evaluated. 4-Methyl-2-phenylselenyl succinate (4) was prepared by the reaction of sodium benzeneselenolate with 2-bromosuccinic anhydrite in methanol solution. The methyl ester was converted to the acid (5) by hydrolysis with aqueous hydrochloric acid. Reaction of the 2-phenylselenyl succinic anhydrite (6) with α-tocopherol (1a), γ-tocopherol (1c), and γ-tocotrienol (2c) in acidic conditions gave the respective esters. The free radical scavenging properties of α-tocopheryl-2-phenylselenyl succinate (7), γ-tocopheryl-2- phenylselenyl succinate (8), and γ-tocotrienyl-2-phenylselenyl succinate (9) were evaluated in comparison with those of α-tocopheryl succinate (10), γ-tocopheryl succinate (11), and γ-tocotrienyl succinate (12), respectively, and the free tocopherols and γ-tocotrienol. Compounds 7-9 induced a statistically significant decrease in prostate cancer cell viability compared to 10-12, respectively, or 5, exhibiting features of apoptotic cell death and associated with caspase-3 activation. These data show that structural modifications of vitamin E components by 5 enhance their apoptogenic properties in cancer cells
ISSN: 09680896
DOI: 10.1016/j.bmc.2005.11.045
Rights: © 2005 Elsevier Ltd. All rights reserved
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