TY - JOUR
T1 - Stereochemical analysis and cytotoxicity of kulokekahilide-2 and its analogues
AU - Umehara, Masahiro
AU - Negishi, Takayuki
AU - Maehara, Yukie
AU - Nakao, Yoichi
AU - Kimura, Junji
N1 - Funding Information:
We thank the Screening Committee of Anticancer Drugs, which is supported by a Grant-in-Aid for Scientific Research on Innovative Areas, Scientific Support Programs for Cancer Research, from The Ministry of Education, Culture, Sports, Science and Technology, Japan, for biological evaluation of compounds 1 , 1c and 1g . This study was funded by the Research Institute of Aoyama Gakuin .
PY - 2013/4/8
Y1 - 2013/4/8
N2 - We report the conformational analysis of kulokekahilide-2, a cytotoxic cyclic depsipeptide, and its analogues. We also evaluated their cytotoxicity against human cancer cells. Although both the cis and trans conformations are possible for the amide bond between MePhe and MeGly, only one conformation was observed in DMSO. We also reveal that the configuration at C-43 in kulokekahilide-2 controls intramolecular ester exchange between the 26- and 24-membered cyclic depsipeptides. Kulokekahilide-2 and its analogues were evaluated for their cell-growth inhibition profile and using COMPARE analysis, which suggested a mechanism of action different from that of standard anticancer drugs.
AB - We report the conformational analysis of kulokekahilide-2, a cytotoxic cyclic depsipeptide, and its analogues. We also evaluated their cytotoxicity against human cancer cells. Although both the cis and trans conformations are possible for the amide bond between MePhe and MeGly, only one conformation was observed in DMSO. We also reveal that the configuration at C-43 in kulokekahilide-2 controls intramolecular ester exchange between the 26- and 24-membered cyclic depsipeptides. Kulokekahilide-2 and its analogues were evaluated for their cell-growth inhibition profile and using COMPARE analysis, which suggested a mechanism of action different from that of standard anticancer drugs.
KW - Cytotoxic evaluation
KW - Intramolecular ester exchange
KW - Kulokekahilide-2
KW - Stereochemical analysis
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U2 - 10.1016/j.tet.2013.01.089
DO - 10.1016/j.tet.2013.01.089
M3 - Article
AN - SCOPUS:84874660805
SN - 0040-4020
VL - 69
SP - 3045
EP - 3053
JO - Tetrahedron
JF - Tetrahedron
IS - 14
ER -
