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Synthesis of a novel series of 2‐methylsulfanyl fatty acids and their toxicity on the human K‐562 and U‐937 leukemia cell lines
Author(s) -
Carballeira Néstor M.,
Miranda Carlos,
Orellano Elsie A.,
González Fernando A.
Publication year - 2005
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-005-1470-5
Subject(s) - cytotoxicity , chemistry , saponification , tetramethylammonium hydroxide , lithium diisopropylamide , leukemia , cytotoxic t cell , decanoic acid , cell culture , stereochemistry , biochemistry , organic chemistry , in vitro , biology , medicine , ion , deprotonation , genetics
The hitherto unknown 2‐methylsulfanyldecanoic acid and 2‐methylsulfanyldodecanoic acid were synthesized from methyl decanoate and methyl dodecanoate, respectively, through the reaction of lithium diisopropylamide and dimethyldisulfide in THF followed by saponification with potassium hydroxide in ethanol. Both α‐methylsulfanylated FA were cytotoxic to the human chronic myelogenous leukemia K‐562 and the human histiocytic lymphoma U‐937 cell lines with EC 50 values in the 200–300 μM range, which makes them more cytotoxic to these cell lines than decanoic and/or dodecanoic acid. The cytotoxicity of the studied FA toward K‐562 followed the order 2‐SCH 3 ‐12∶0>2‐SCH 3 ‐10∶0>10∶0>12∶0>2‐OCH 3 ‐12∶0, whereas toward U‐937 the cytotoxicity was 2‐SCH 3 ‐10∶0>2‐SCH 3 ‐12∶0>12∶0>10∶0>2‐OCH 3 ‐12∶0. These results indicate that the α‐methylsulfanyl substitution increases the cytotoxicity of the C 10 and C 12 FA toward the studied leukemia cell lines.