Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/19577
Title: Total synthesis and biological evaluation of grassypeptolide A
Authors: Liu, H
Liu, Y
Wang, Z
Xing, X
Maguire, AR
Luesch, H
Zhang, H
Xu, Z
Ye, T 
Issue Date: 2013
Source: Chemistry - a European journal, 2013, v. 19, no. 21, p. 6774-6784
Abstract: Herein, we describe in full our investigations into the synthesis of grassypeptolide A (1) in 17 linear steps with an overall yield of 11.3 %. In particular, this work features the late-stage introduction of sensitive bis(thiazoline) heterocycles and 31-membered macrocyclization conducted at the sterically congested secondary amide site in superb conversion (72 % yield). Biological evaluation indicated that grassypeptolide A significantly inhibited cancer cell proliferation in a dose-dependent manner. It induced cancer cell apoptosis, which was associated with increased cleavage of poly(ADP-ribose) polymerase (PARP) and decreased expression of bcl-2 and bcl-xL. Furthermore, grassypeptolide A also caused cell cycle redistribution by increasing cells in the G1 phase and decreasing cells in the S and G2 phases. In addition, cell cycle arrest was correlated with downregulation of cyclin D and upregulation of p27 and p21. Cytotoxic activity: Synthesis of grassypeptolide A, an anticancer marine cyclodepsipeptide, in 17 linear steps with an overall yield of 11.3 % is described (see figure). Subsequent biological evaluation indicated that grassypeptolide A significantly inhibited cancer-cell proliferation in a dose-dependent manner.
Keywords: cyclodepsipeptides
cytotoxicity
grassypeptolide
thiazolines
total synthesis
Publisher: Wiley-VCH
Journal: Chemistry - a European journal 
ISSN: 0947-6539
EISSN: 1521-3765
DOI: 10.1002/chem.201203667
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