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Cytotoxic Activities of Amino Acid‐Conjugate Derivatives of Abietane‐Type Diterpenoids against Human Cancer Cell Lines
Author(s) -
Ukiya Motohiko,
Kawaguchi Takuma,
Ishii Kenta,
Ogihara Eri,
Tachi Yosuke,
Kurita Masahiro,
Ezaki Yoichiro,
Fukatsu Makoto,
Kushi Yasunori,
Akihisa Toshihiro
Publication year - 2013
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201300043
Subject(s) - hl60 , abietane , chemistry , cytotoxic t cell , cytotoxicity , abietic acid , cell culture , conjugate , stereochemistry , a549 cell , cancer cell , leukemia , cancer , biochemistry , apoptosis , in vitro , diterpene , biology , organic chemistry , immunology , mathematical analysis , mathematics , resin acid , genetics , rosin
Nine amino acid conjugate derivatives, each 2 – 10 and 12 – 20 , were prepared from abietic acid ( 1 ) and dehydroabietic acid ( 11 ), respectively, and they were evaluated for their cytotoxicities against four human cancer cell lines, i.e. , leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK‐BR‐3). All compounds showed cytotoxicities against HL60 with IC 50 values in the range of 2.3–37.3 μ M . In addition, most of the derivatives exhibited moderate cytotoxicities against the other cancer cell lines. Among the derivatives, methyl N ‐[18‐oxoabieta‐8,11,13‐trien‐18‐yl]‐ L ‐tyrosinate ( 19 ) exhibited potent cytotoxic activities against four cancer cell lines with IC 50 values of 2.3 (HL60), 7.1 (A549), 3.9 (AZ521), and 8.1 μ M (SK‐BR‐3). Furthermore, all derivatives were shown to possess high selective cytotoxic activities for leukemia cells, since they exhibited only weak cytotoxicities against normal lymphocyte cell line RPMI1788.