Literature DB >> 19594124

Synthesis of phosphatase-stable, cell-permeable peptidomimetic prodrugs that target the SH2 domain of Stat3.

Pijus K Mandal1, Warren S-L Liao, John S McMurray.   

Abstract

The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.

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Year:  2009        PMID： 19594124      PMCID： PMC2836187          DOI： 10.1021/ol9012662

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Effect of potent and selective inhibitors of the Grb2 SH2 domain on cell motility.

Authors:  B Gay; S Suarez; C Weber; J Rahuel; D Fabbro; P Furet; G Caravatti; J Schoepfer
Journal:  J Biol Chem       Date:  1999-08-13       Impact factor: 5.157

Review 2.  Phosphoryltyrosyl mimetics in the design of peptide-based signal transduction inhibitors.

Authors:  T R Burke; Z J Yao; D G Liu; J Voigt; Y Gao
Journal:  Biopolymers       Date:  2001       Impact factor: 2.505

Review 3.  Transcription factors as targets for cancer therapy.

Authors:  James E Darnell
Journal:  Nat Rev Cancer       Date:  2002-10       Impact factor: 60.716

Review 4.  The STATs of cancer--new molecular targets come of age.

Authors:  Hua Yu; Richard Jove
Journal:  Nat Rev Cancer       Date:  2004-02       Impact factor: 60.716

5.  Conformationally constrained peptidomimetic inhibitors of signal transducer and activator of transcription. 3: Evaluation and molecular modeling.

Authors:  Pijus K Mandal; Donald Limbrick; David R Coleman; Garrett A Dyer; Zhiyong Ren; J Sanderson Birtwistle; Chiyi Xiong; Xiaomin Chen; James M Briggs; John S McMurray
Journal:  J Med Chem       Date:  2009-04-23       Impact factor: 7.446

6.  Selective GRB2 SH2 inhibitors as anti-Ras therapy.

Authors:  B Gay; S Suarez; G Caravatti; P Furet; T Meyer; J Schoepfer
Journal:  Int J Cancer       Date:  1999-10-08       Impact factor: 7.396

7.  Inhibition of the ras-dependent mitogenic pathway by phosphopeptide prodrugs with antiproliferative properties.

Authors:  W Q Liu; M Vidal; C Mathé; C Périgaud; C Garbay
Journal:  Bioorg Med Chem Lett       Date:  2000-04-03       Impact factor: 2.823

8.  Synthesis and antitumor evaluation of bis[(pivaloyloxy)methyl] 2'-deoxy-5-fluorouridine 5'-monophosphate (FdUMP): a strategy to introduce nucleotides into cells.

Authors:  D Farquhar; S Khan; D N Srivastva; P P Saunders
Journal:  J Med Chem       Date:  1994-11-11       Impact factor: 7.446

9.  Structure-activity relationships of small phosphopeptides, inhibitors of Grb2 SH2 domain, and their prodrugs.

Authors:  Wang-Qing Liu; Michel Vidal; Catherine Olszowy; Emmanuelle Million; Christine Lenoir; Hélène Dhôtel; Christiane Garbay
Journal:  J Med Chem       Date:  2004-02-26       Impact factor: 7.446

Review 10.  Phosphotyrosyl mimetics in the development of signal transduction inhibitors.

Authors:  Terrence R Burke; Kyeong Lee
Journal:  Acc Chem Res       Date:  2003-06       Impact factor: 22.384
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  29 in total

1.  Small molecule targeting of the STAT5/6 Src homology 2 (SH2) domains to inhibit allergic airway disease.

Authors:  J Morgan Knight; Pijus Mandal; Pietro Morlacchi; Garbo Mak; Evan Li; Matthew Madison; Cameron Landers; Brandon Saxton; Ed Felix; Brian Gilbert; Joel Sederstrom; Atul Varadhachary; Melissa M Singh; Dev Chatterjee; David B Corry; John S McMurray
Journal:  J Biol Chem       Date:  2018-05-08       Impact factor: 5.157

2.  Design and synthesis of a reagent for solid-phase incorporation of the phosphothreonine mimetic (2S,3R)-2-amino-3-methyl-4-phosphonobutyric acid (Pmab) into peptides in a bio-reversible phosphonyl-bis-pivaloyloxymethyl (POM) prodrug form.

Authors:  Wen-Jian Qian; Terrence R Burke
Journal:  Amino Acids       Date:  2013-08-02       Impact factor: 3.520

Review 3.  Prodrugs of phosphonates and phosphates: crossing the membrane barrier.

Authors:  Andrew J Wiemer; David F Wiemer
Journal:  Top Curr Chem       Date:  2015

4.  Structure-Based Design of Conformationally Constrained, Cell-Permeable STAT3 Inhibitors.

Authors:  Jianyong Chen; Longchuan Bai; Denzil Bernard; Zaneta Nikolovska-Coleska; Cindy Gomez; Jian Zhang; Han Yi; Shaomeng Wang
Journal:  ACS Med Chem Lett       Date:  2010-05-13       Impact factor: 4.345

Review 5.  Phosphotyrosine isosteres: past, present and future.

Authors:  Robert A Cerulli; Joshua A Kritzer
Journal:  Org Biomol Chem       Date:  2019-11-28       Impact factor: 3.876

6.  Potent and selective phosphopeptide mimetic prodrugs targeted to the Src homology 2 (SH2) domain of signal transducer and activator of transcription 3.

Authors:  Pijus K Mandal; Fengqin Gao; Zhen Lu; Zhiyong Ren; Rajagopal Ramesh; J Sanderson Birtwistle; Kumaralal K Kaluarachchi; Xiaomin Chen; Robert C Bast; Warren S Liao; John S McMurray
Journal:  J Med Chem       Date:  2011-04-26       Impact factor: 7.446

7.  Cytosolic delivery of peptidic STAT3 SH2 domain inhibitors.

Authors:  Robert A Cerulli; Livia Shehaj; Isidora Tosic; Kevin Jiang; Jing Wang; David A Frank; Joshua A Kritzer
Journal:  Bioorg Med Chem       Date:  2020-05-04       Impact factor: 3.641

Review 8.  Targeting SH2 domains in breast cancer.

Authors:  Pietro Morlacchi; Fredika M Robertson; Jim Klostergaard; John S McMurray
Journal:  Future Med Chem       Date:  2014       Impact factor: 3.808

9.  Identification of novel inhibitors that disrupt STAT3-DNA interaction from a γ-AApeptide OBOC combinatorial library.

Authors:  Peng Teng; Xiaolei Zhang; Haifan Wu; Qiao Qiao; Said M Sebti; Jianfeng Cai
Journal:  Chem Commun (Camb)       Date:  2014-06-25       Impact factor: 6.222

10.  A phosphopeptide mimetic prodrug targeting the SH2 domain of Stat3 inhibits tumor growth and angiogenesis.

Authors:  Edmond J Auzenne; Jim Klostergaard; Pijus K Mandal; Warren S Liao; Zhen Lu; Fengqin Gao; Robert C Bast; Fredika M Robertson; John S McMurray
Journal:  J Exp Ther Oncol       Date:  2012
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