Literature DB >> 21680182

Design, synthesis and evaluation of monovalent Smac mimetics that bind to the BIR2 domain of the anti-apoptotic protein XIAP.

Marcos González-López1, Kate Welsh, Darren Finlay, Robert J Ardecky, Santhi Reddy Ganji, Ying Su, Hongbin Yuan, Peter Teriete, Peter D Mace, Stefan J Riedl, Kristiina Vuori, John C Reed, Nicholas D P Cosford.   

Abstract

We report the systematic rational design and synthesis of new monovalent Smac mimetics that bind preferentially to the BIR2 domain of the anti-apoptotic protein XIAP. Characterization of compounds in vitro (including 9i; ML101) led to the determination of key structural requirements for BIR2 binding affinity. Compounds 9h and 9j sensitized TRAIL-resistant breast cancer cells to apoptotic cell death, highlighting the value of these probe compounds as tools to investigate the biology of XIAP.
Copyright © 2011 Elsevier Ltd. All rights reserved.

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Year:  2011        PMID： 21680182      PMCID： PMC3440873          DOI： 10.1016/j.bmcl.2011.05.049

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  26 in total

1.  Structural basis of caspase-7 inhibition by XIAP.

Authors:  J Chai; E Shiozaki; S M Srinivasula; Q Wu; P Datta; E S Alnemri; Y Shi; P Dataa
Journal:  Cell       Date:  2001-03-09       Impact factor: 41.582

2.  Structural basis for the inhibition of caspase-3 by XIAP.

Authors:  S J Riedl; M Renatus; R Schwarzenbacher; Q Zhou; C Sun; S W Fesik; R C Liddington; G S Salvesen
Journal:  Cell       Date:  2001-03-09       Impact factor: 41.582

Review 3.  IAP family proteins--suppressors of apoptosis.

Authors:  Q L Deveraux; J C Reed
Journal:  Genes Dev       Date:  1999-02-01       Impact factor: 11.361

Review 4.  Apoptosis in cancer.

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

5.  Structural basis of caspase inhibition by XIAP: differential roles of the linker versus the BIR domain.

Authors:  Y Huang; Y C Park; R L Rich; D Segal; D G Myszka; H Wu
Journal:  Cell       Date:  2001-03-09       Impact factor: 41.582

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

Review 7.  Caspases, IAPs and Smac/DIABLO: mechanisms from structural biology.

Authors:  Eric N Shiozaki; Yigong Shi
Journal:  Trends Biochem Sci       Date:  2004-09       Impact factor: 13.807

8.  Development and optimization of a binding assay for the XIAP BIR3 domain using fluorescence polarization.

Authors:  Zaneta Nikolovska-Coleska; Renxiao Wang; Xueliang Fang; Hongguang Pan; York Tomita; Peng Li; Peter P Roller; Krzysztof Krajewski; Naoyuki G Saito; Jeanne A Stuckey; Shaomeng Wang
Journal:  Anal Biochem       Date:  2004-09-15       Impact factor: 3.365

9.  Discovery of potent antagonists of the antiapoptotic protein XIAP for the treatment of cancer.

Authors:  Thorsten K Oost; Chaohong Sun; Robert C Armstrong; Ali-Samer Al-Assaad; Stephen F Betz; Thomas L Deckwerth; Hong Ding; Steven W Elmore; Robert P Meadows; Edward T Olejniczak; Andrew Oleksijew; Tilman Oltersdorf; Saul H Rosenberg; Alexander R Shoemaker; Kevin J Tomaselli; Hua Zou; Stephen W Fesik
Journal:  J Med Chem       Date:  2004-08-26       Impact factor: 7.446

10.  Small-molecule antagonists of apoptosis suppressor XIAP exhibit broad antitumor activity.

Authors:  Aaron D Schimmer; Kate Welsh; Clemencia Pinilla; Zhiliang Wang; Maryla Krajewska; Marie-Josee Bonneau; Irene M Pedersen; Shinichi Kitada; Fiona L Scott; Beatrice Bailly-Maitre; Gennadi Glinsky; Dominick Scudiero; Edward Sausville; Guy Salvesen; Adel Nefzi; John M Ostresh; Richard A Houghten; John C Reed
Journal:  Cancer Cell       Date:  2004-01       Impact factor: 31.743
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  11 in total

1.  A critical role for cellular inhibitor of protein 2 (cIAP2) in colitis-associated colorectal cancer and intestinal homeostasis mediated by the inflammasome and survival pathways.

Authors:  M Dagenais; J Dupaul-Chicoine; C Champagne; A Skeldon; A Morizot; M Saleh
Journal:  Mucosal Immunol       Date:  2015-06-03       Impact factor: 7.313

Review 2.  Targeting IAP proteins for therapeutic intervention in cancer.

Authors:  Simone Fulda; Domagoj Vucic
Journal:  Nat Rev Drug Discov       Date:  2012-02-01       Impact factor: 84.694

3.  Design, synthesis and evaluation of inhibitor of apoptosis protein (IAP) antagonists that are highly selective for the BIR2 domain of XIAP.

Authors:  Robert J Ardecky; Kate Welsh; Darren Finlay; Pooi San Lee; Marcos González-López; Santhi Reddy Ganji; Palaniyandi Ravanan; Peter D Mace; Stefan J Riedl; Kristiina Vuori; John C Reed; Nicholas D P Cosford
Journal:  Bioorg Med Chem Lett       Date:  2013-05-14       Impact factor: 2.823

4.  Expedient synthesis of highly potent antagonists of inhibitor of apoptosis proteins (IAPs) with unique selectivity for ML-IAP.

Authors:  Mitchell Vamos; Kate Welsh; Darren Finlay; Pooi San Lee; Peter D Mace; Scott J Snipas; Monica L Gonzalez; Santhi Reddy Ganji; Robert J Ardecky; Stefan J Riedl; Guy S Salvesen; Kristiina Vuori; John C Reed; Nicholas D P Cosford
Journal:  ACS Chem Biol       Date:  2013-02-05       Impact factor: 5.100

5.  Small-molecule IAP antagonists sensitize cancer cells to TRAIL-induced apoptosis: roles of XIAP and cIAPs.

Authors:  Darren Finlay; Mitchell Vamos; Marcos González-López; Robert J Ardecky; Santhi Reddy Ganji; Hongbin Yuan; Ying Su; Trina R Cooley; Curt T Hauser; Kate Welsh; John C Reed; Nicholas D P Cosford; Kristiina Vuori
Journal:  Mol Cancer Ther       Date:  2013-11-05       Impact factor: 6.261

6.  The structure of XIAP BIR2: understanding the selectivity of the BIR domains.

Authors:  Christine Lukacs; Charles Belunis; Robert Crowther; Waleed Danho; Lin Gao; Barry Goggin; Cheryl A Janson; Shirley Li; Stacy Remiszewski; Andrew Schutt; Manish K Thakur; Saroj K Singh; Srinivasan Swaminathan; Rajat Pandey; Rajiv Tyagi; Ramachandraiah Gosu; Ajith V Kamath; Andreas Kuglstatter
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2013-08-15

Review 7.  X-linked inhibitor of apoptosis protein - a critical death resistance regulator and therapeutic target for personalized cancer therapy.

Authors:  Petra Obexer; Michael J Ausserlechner
Journal:  Front Oncol       Date:  2014-07-28       Impact factor: 6.244

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.  Characterization of Potent SMAC Mimetics that Sensitize Cancer Cells to TNF Family-Induced Apoptosis.

Authors:  Kate Welsh; Snezana Milutinovic; Robert J Ardecky; Marcos Gonzalez-Lopez; Santhi Reddy Ganji; Peter Teriete; Darren Finlay; Stefan Riedl; Shu-Ichi Matsuzawa; Clemencia Pinilla; Richard Houghten; Kristiina Vuori; John C Reed; Nicholas D P Cosford
Journal:  PLoS One       Date:  2016-09-12       Impact factor: 3.240

10.  Investigating isoquinoline derivatives for inhibition of inhibitor of apoptosis proteins for ovarian cancer treatment.

Authors:  Chen Chen; Jie Wu; Pengfei Zhu; Congjian Xu; Liangqing Yao
Journal:  Drug Des Devel Ther       Date:  2017-09-11       Impact factor: 4.162
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