Literature DB >> 19012392

Design, synthesis, and evaluation of tricyclic, conformationally constrained small-molecule mimetics of second mitochondria-derived activator of caspases.

Bin Zhang1, Zaneta Nikolovska-Coleska, Yan Zhang, Longchuan Bai, Su Qiu, Chao-Yie Yang, Haiying Sun, Shaomeng Wang, Yikang Wu.   

Abstract

A series of tricyclic, conformationally constrained Smac mimetics have been designed, synthesized, and evaluated. The most potent compound 6 (WS-5) binds to XIAP, cIAP-1, and cIAP-2 with K(i) of 18, 1.1, and 4.2 nM, respectively. Compound 6 antagonizes XIAP in a functional assay, induces cIAP-1 degradation, inhibits cell growth with an IC(50) of 68 nM in the MDA-MB-231 cancer cell line, and effectively induces cancer cells to undergo apoptosis.

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Year:  2008        PMID： 19012392      PMCID： PMC2662380          DOI： 10.1021/jm801146d

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


  25 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.  Apoptosis-based therapies.

Authors:  John C Reed
Journal:  Nat Rev Drug Discov       Date:  2002-02       Impact factor: 84.694

Review 3.  XIAP: apoptotic brake and promising therapeutic target.

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

4.  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

5.  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

Review 6.  Apoptosis in cancer.

Authors:  S W Lowe; A W Lin
Journal:  Carcinogenesis       Date:  2000-03       Impact factor: 4.944

7.  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

8.  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

9.  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

10.  Identification of DIABLO, a mammalian protein that promotes apoptosis by binding to and antagonizing IAP proteins.

Authors:  A M Verhagen; P G Ekert; M Pakusch; J Silke; L M Connolly; G E Reid; R L Moritz; R J Simpson; D L Vaux
Journal:  Cell       Date:  2000-07-07       Impact factor: 41.582
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  7 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

2.  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

3.  Novel second mitochondria-derived activator of caspases (Smac) mimetic compounds sensitize human leukemic cell lines to conventional chemotherapeutic drug-induced and death receptor-mediated apoptosis.

Authors:  Federica Servida; Daniele Lecis; Cinzia Scavullo; Carmelo Drago; Pierfausto Seneci; Carmelo Carlo-Stella; Leonardo Manzoni; Elio Polli; Giorgio Lambertenghi Deliliers; Domenico Delia; Francesco Onida
Journal:  Invest New Drugs       Date:  2010-07-08       Impact factor: 3.850

4.  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

5.  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

Review 6.  Potency and Selectivity of SMAC/DIABLO Mimetics in Solid Tumor Therapy.

Authors:  Xiao-Yun Zhao; Xiu-Yun Wang; Qi-Yao Wei; Yan-Ming Xu; Andy T Y Lau
Journal:  Cells       Date:  2020-04-18       Impact factor: 6.600

7.  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
  7 in total

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