Literature DB >> 19049347

Potent, orally bioavailable diazabicyclic small-molecule mimetics of second mitochondria-derived activator of caspases.

Yuefeng Peng1, Haiying Sun, Zaneta Nikolovska-Coleska, Su Qiu, Chao-Yie Yang, Jianfeng Lu, Qian Cai, Han Yi, Sanmao Kang, Dajun Yang, Shaomeng Wang.   

Abstract

A series of small-molecule Smac mimetics containing a diazabicyclic core structure have been designed, synthesized, and evaluated. The most potent compound (6) binds to XIAP, cIAP-1, and cIAP-2 with K(i) values of 8.4, 1.5, and 4.2 nM, respectively, directly antagonizes XIAP in a cell-free functional assay and induces cIAP-1 degradation in cancer cells. It inhibits cell growth with an IC(50) value of 31 nM, effectively induces apoptosis in the MDA-MB-231 cancer cell line, and has a good oral bioavailability.

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Year:  2008        PMID： 19049347      PMCID： PMC2679375          DOI： 10.1021/jm801254r

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  23 in total

Review 1.  IAP proteins: blocking the road to death's door.

Authors:  Guy S Salvesen; Colin S Duckett
Journal:  Nat Rev Mol Cell Biol       Date:  2002-06       Impact factor: 94.444

Review 2.  XIAP: apoptotic brake and promising therapeutic target.

Authors:  M Holcik; H Gibson; R G Korneluk
Journal:  Apoptosis       Date:  2001-08       Impact factor: 4.677

3.  Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP.

Authors:  Haiying Sun; Zaneta Nikolovska-Coleska; Jianfeng Lu; Jennifer L Meagher; Chao-Yie Yang; Su Qiu; York Tomita; Yumi Ueda; Sheng Jiang; Krzysztof Krajewski; Peter P Roller; Jeanne A Stuckey; Shaomeng Wang
Journal:  J Am Chem Soc       Date:  2007-11-14       Impact factor: 15.419

4.  A conserved XIAP-interaction motif in caspase-9 and Smac/DIABLO regulates caspase activity and apoptosis.

Authors:  S M Srinivasula; R Hegde; A Saleh; P Datta; E Shiozaki; J Chai; R A Lee; P D Robbins; T Fernandes-Alnemri; Y Shi; E S Alnemri
Journal:  Nature       Date:  2001-03-01       Impact factor: 49.962

5.  Mechanism of XIAP-mediated inhibition of caspase-9.

Authors:  Eric N Shiozaki; Jijie Chai; Daniel J Rigotti; Stefan J Riedl; Pingwei Li; Srinivasa M Srinivasula; Emad S Alnemri; Robert Fairman; Yigong Shi
Journal:  Mol Cell       Date:  2003-02       Impact factor: 17.970

6.  Structural basis for binding of Smac/DIABLO to the XIAP BIR3 domain.

Authors:  Z Liu; C Sun; E T Olejniczak; R P Meadows; S F Betz; T Oost; J Herrmann; J C Wu; S W Fesik
Journal:  Nature       Date:  2000 Dec 21-28       Impact factor: 49.962

7.  Structural basis of IAP recognition by Smac/DIABLO.

Authors:  G Wu; J Chai; T L Suber; J W Wu; C Du; X Wang; Y Shi
Journal:  Nature       Date:  2000 Dec 21-28       Impact factor: 49.962

8.  Smac, a mitochondrial protein that promotes cytochrome c-dependent caspase activation by eliminating IAP inhibition.

Authors:  C Du; M Fang; Y Li; L Li; X Wang
Journal:  Cell       Date:  2000-07-07       Impact factor: 41.582

9.  A JNK-dependent pathway is required for TNFalpha-induced apoptosis.

Authors:  Yibin Deng; Xiaoyang Ren; Lin Yang; Yahong Lin; Xiangwei Wu
Journal:  Cell       Date:  2003-10-03       Impact factor: 41.582

10.  Apoptotic crosstalk of TNF receptors: TNF-R2-induces depletion of TRAF2 and IAP proteins and accelerates TNF-R1-dependent activation of caspase-8.

Authors:  Mariola Fotin-Mleczek; Frank Henkler; Dierk Samel; Monica Reichwein; Angelika Hausser; Ingela Parmryd; Peter Scheurich; Johannes A Schmid; Harald Wajant
Journal:  J Cell Sci       Date:  2002-07-01       Impact factor: 5.285
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  12 in total

1.  A potent bivalent Smac mimetic (SM-1200) achieving rapid, complete, and durable tumor regression in mice.

Authors:  Rong Sheng; Haiying Sun; Liu Liu; Jianfeng Lu; Donna McEachern; Guanfeng Wang; Jianfeng Wen; Ping Min; Zhenyun Du; Huirong Lu; Sanmao Kang; Ming Guo; Dajun Yang; Shaomeng Wang
Journal:  J Med Chem       Date:  2013-05-07       Impact factor: 7.446

Review 2.  Enhanced interrogation: emerging strategies for cell signaling inhibition.

Authors:  Rong Huang; Isabel Martinez-Ferrando; Philip A Cole
Journal:  Nat Struct Mol Biol       Date:  2010-06       Impact factor: 15.369

3.  A potent and orally active antagonist (SM-406/AT-406) of multiple inhibitor of apoptosis proteins (IAPs) in clinical development for cancer treatment.

Authors:  Qian Cai; Haiying Sun; Yuefeng Peng; Jianfeng Lu; Zaneta Nikolovska-Coleska; Donna McEachern; Liu Liu; Su Qiu; Chao-Yie Yang; Rebecca Miller; Han Yi; Tao Zhang; Duxin Sun; Sanmao Kang; Ming Guo; Lance Leopold; Dajun Yang; Shaomeng Wang
Journal:  J Med Chem       Date:  2011-03-28       Impact factor: 7.446

4.  Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins.

Authors:  Haiying Sun; Jianfeng Lu; Liu Liu; Han Yi; Su Qiu; Chao-Yie Yang; Jeffrey R Deschamps; Shaomeng Wang
Journal:  J Med Chem       Date:  2010-09-09       Impact factor: 7.446

5.  Potent bivalent Smac mimetics: effect of the linker on binding to inhibitor of apoptosis proteins (IAPs) and anticancer activity.

Authors:  Haiying Sun; Liu Liu; Jianfeng Lu; Longchuan Bai; Xiaoqin Li; Zaneta Nikolovska-Coleska; Donna McEachern; Chao-Yie Yang; Su Qiu; Han Yi; Duxin Sun; Shaomeng Wang
Journal:  J Med Chem       Date:  2011-04-13       Impact factor: 7.446

6.  Importance of ligand reorganization free energy in protein-ligand binding-affinity prediction.

Authors:  Chao-Yie Yang; Haiying Sun; Jianyong Chen; Zaneta Nikolovska-Coleska; Shaomeng Wang
Journal:  J Am Chem Soc       Date:  2009-09-30       Impact factor: 15.419

7.  Targeted pancreatic cancer therapy with the small molecule drug conjugate SW IV-134.

Authors:  Yassar M Hashim; Dirk Spitzer; Suwanna Vangveravong; Mary C Hornick; Gunjal Garg; John R Hornick; Peter Goedegebuure; Robert H Mach; William G Hawkins
Journal:  Mol Oncol       Date:  2014-03-26       Impact factor: 6.603

Review 8.  Inducing death in tumor cells: roles of the inhibitor of apoptosis proteins.

Authors:  Darren Finlay; Peter Teriete; Mitchell Vamos; Nicholas D P Cosford; Kristiina Vuori
Journal:  F1000Res       Date:  2017-04-27

9.  The Targeted SMAC Mimetic SW IV-134 is a strong enhancer of standard chemotherapy in pancreatic cancer.

Authors:  Yassar M Hashim; Suwanna Vangveravong; Narendra V Sankpal; Pratibha S Binder; Jingxia Liu; S Peter Goedegebuure; Robert H Mach; Dirk Spitzer; William G Hawkins
Journal:  J Exp Clin Cancer Res       Date:  2017-01-17

10.  Potent and selective small-molecule inhibitors of cIAP1/2 proteins reveal that the binding of Smac mimetics to XIAP BIR3 is not required for their effective induction of cell death in tumor cells.

Authors:  Haiying Sun; Jianfeng Lu; Liu Liu; Chao-Yie Yang; Shaomeng Wang
Journal:  ACS Chem Biol       Date:  2014-02-12       Impact factor: 5.100
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