Exploring the potential of the β-thiolactones in bioorganic chemistry

被引:16
作者
Aubry, Sylvain [1 ]
Sasaki, Kaname [1 ]
Eloy, Laure [1 ]
Aubert, Genevieve [1 ]
Retailleau, Pascal [1 ]
Cresteil, Thierry [1 ]
Crich, David [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91190 Gif Sur Yvette, France
关键词
CYSTEINE PROTEINASE-INHIBITORS; FREE-RADICAL CHEMISTRY; PROTEASOME INHIBITORS; SALINOSPORAMIDE-A; MOLECULAR-STRUCTURE; COUPLING REACTIONS; CANCER-THERAPY; ACTIVE-SITE; CATHEPSIN-B; LACTONES;
D O I
10.1039/c1ob05967j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel peptide-based beta-thiolactones were synthesized and assayed for cytotoxicity against several human cancer cell lines, where they showed greater activity than the corresponding beta-lactones and beta-lactams. Several of the beta-thiolactones prepared showed strong inhibitory activity in vitro against human cathepsins B and L.
引用
收藏
页码:7134 / 7143
页数:10
相关论文
共 99 条
[91]   Activity-Based Proteome Profiling of Potential Cellular Targets of Orlistat - An FDA-Approved Drug with Anti-Tumor Activities [J].
Yang, Peng-Yu ;
Liu, Kai ;
Ngai, Mun Hong ;
Lear, Martin J. ;
Wenk, Markus R. ;
Yao, Shao Q. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (02) :656-666
[92]   Dual modes of modification of hepatitis A virus 3C protease by a serine-derived β-lactone:: Selective crystallization and formation of a functional catalytic triad in the active site [J].
Yin, J ;
Bergmann, EM ;
Cherney, MM ;
Lall, MS ;
Jain, RP ;
Vederas, JC ;
James, MNG .
JOURNAL OF MOLECULAR BIOLOGY, 2005, 354 (04) :854-871
[93]   Three-dimensional structure-activity relationship study of belactosin A and its stereo- and regioisomers: development of potent proteasome inhibitors by a stereochemical diversity-oriented strategy [J].
Yoshida, Keisuke ;
Yamaguchi, Kazuya ;
Mizuno, Akira ;
Unno, Yuka ;
Asai, Akira ;
Sone, Takayuki ;
Yokosawa, Hideyoshi ;
Matsuda, Akira ;
Arisawa, Mitsuhiro ;
Shuto, Satoshi .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (09) :1868-1877
[94]   REDUCTION IN MITOCHONDRIAL POTENTIAL CONSTITUTES AN EARLY IRREVERSIBLE STEP OF PROGRAMMED LYMPHOCYTE DEATH IN-VIVO [J].
ZAMZAMI, N ;
MARCHETTI, P ;
CASTEDO, M ;
ZANIN, C ;
VAYSSIERE, JL ;
PETIT, PX ;
KROEMER, G .
JOURNAL OF EXPERIMENTAL MEDICINE, 1995, 181 (05) :1661-1672
[95]  
ZAUGG HE, 1954, ORG REACTIONS, V8, P305
[96]   3-acylamino-azetidin-2-one as a novel class of cysteine proteases inhibitors [J].
Zhou, NE ;
Guo, DQ ;
Thomas, G ;
Reddy, AVN ;
Kaleta, J ;
Purisima, E ;
Menard, R ;
Micetich, RG ;
Singh, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (01) :139-141
[97]   6-acylamino-penam derivatives: Synthesis and inhibition of cathepsins B, L, K, and S [J].
Zhou, NE ;
Kaleta, J ;
Purisima, E ;
Menard, R ;
Micetich, RG ;
Singh, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (23) :3417-3419
[98]   Design and synthesis of 6-substituted amino-4-oxa-1-azabicyclo[3,2,0]heptan-7-one derivatives as cysteine proteases inhibitors [J].
Zhou, NE ;
Guo, DQ ;
Kaleta, J ;
Purisima, E ;
Menard, R ;
Micetich, RG ;
Singh, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (23) :3413-3415
[99]   Synthesis of (±)- and (-)-vibralactone and vibralactone C [J].
Zhou, Quan ;
Snider, Barry B. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20) :8049-8056