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Literature DB >> 17935986

A phosphorylated prodrug for the inhibition of Pin1.

Abstract

Fmoc-pSer-Psi[(Z)CHC]-Pro-(2)-N-(3)-ethylaminoindole 1, showed moderate inhibition towards the mitotic regulator, Pin1 (IC(50)=28.3microM). To improve the cell permeability, the charged phosphate was masked as the bis-pivaloyloxymethyl (POM) phosphate in Fmoc-(bisPOM)-pSer-Psi[(Z)CHC]-Pro-(2)-N-(3)-ethylaminoindole 2. Antiproliferative activity towards A2780 ovarian cancer cells of 1 (IC(50)=46.2microM) was improved significantly in 2 (IC(50)=26.9microM), comparable to the IC(50) of 1 towards Pin1 enzymatic activity.

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Year: 2007 PMID： 17935986 PMCID： PMC2277516 DOI： 10.1016/j.bmcl.2007.09.073

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

27 in total

1. Membrane-permeant derivatives of mannose-1-phosphate.

Authors: Synke Rutschow; Joachim Thiem; Christian Kranz; Thorsten Marquardt
Journal: Bioorg Med Chem Date: 2002-12 Impact factor: 3.641

2. A signalling pathway controlling c-Myc degradation that impacts oncogenic transformation of human cells.

Authors: Elizabeth Yeh; Melissa Cunningham; Hugh Arnold; Dawn Chasse; Teresa Monteith; Giovanni Ivaldi; William C Hahn; P Todd Stukenberg; Shirish Shenolikar; Takafumi Uchida; Christopher M Counter; Joseph R Nevins; Anthony R Means; Rosalie Sears
Journal: Nat Cell Biol Date: 2004-03-14 Impact factor: 28.824

3. Enzymatic and cellular study of a serotonin N-acetyltransferase phosphopantetheine-based prodrug.

Authors: Yousang Hwang; Surajit Ganguly; Anthony K Ho; David C Klein; Philip A Cole
Journal: Bioorg Med Chem Date: 2006-12-13 Impact factor: 3.641

4. The essential mitotic peptidyl-prolyl isomerase Pin1 binds and regulates mitosis-specific phosphoproteins.

Authors: M Shen; P T Stukenberg; M W Kirschner; K P Lu
Journal: Genes Dev Date: 1998-03-01 Impact factor: 11.361

5. Cyclophilin Inhibition by a (Z)-Alkene cis-Proline Mimic.

Authors: Scott A. Hart; Felicia A. Etzkorn
Journal: J Org Chem Date: 1999-04-30 Impact factor: 4.354

6. Prevalent overexpression of prolyl isomerase Pin1 in human cancers.

Authors: Lere Bao; Amy Kimzey; Guido Sauter; Janusz M Sowadski; Kun Ping Lu; Da-Gong Wang
Journal: Am J Pathol Date: 2004-05 Impact factor: 4.307

7. Design, synthesis, and biological evaluation of indolequinone phosphoramidate prodrugs targeted to DT-diaphorase.

Authors: Marcy Hernick; Carolee Flader; Richard F Borch
Journal: J Med Chem Date: 2002-08-01 Impact factor: 7.446

8. Serine-cis-proline and serine-trans-proline isosteres: stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements.

Authors: Xiaodong J Wang; Scott A Hart; Bailing Xu; Matthew D Mason; John R Goodell; Felicia A Etzkorn
Journal: J Org Chem Date: 2003-03-21 Impact factor: 4.354

9. Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate.

Authors: I Lefebvre; C Périgaud; A Pompon; A M Aubertin; J L Girardet; A Kirn; G Gosselin; J L Imbach
Journal: J Med Chem Date: 1995-09-29 Impact factor: 7.446

10. Structural basis for high-affinity peptide inhibition of human Pin1.

Authors: Yan Zhang; Sebastian Daum; Dirk Wildemann; Xiao Zhen Zhou; Mark A Verdecia; Marianne E Bowman; Christian Lücke; Tony Hunter; Kun-Ping Lu; Gunter Fischer; Joseph P Noel
Journal: ACS Chem Biol Date: 2007-05-22 Impact factor: 5.100

12 in total

1. A reduced-amide inhibitor of Pin1 binds in a conformation resembling a twisted-amide transition state.

Authors: Guoyan G Xu; Yan Zhang; Ana Y Mercedes-Camacho; Felicia A Etzkorn
Journal: Biochemistry Date: 2011-10-18 Impact factor: 3.162

2. Synthesis of a phosphoserine mimetic prodrug with potent 14-3-3 protein inhibitory activity.

Authors: Allison Arrendale; Keunho Kim; Jun Young Choi; Wei Li; Robert L Geahlen; Richard F Borch
Journal: Chem Biol Date: 2012-06-22

3. 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

A phosphorylated prodrug for the inhibition of Pin1.

1. Membrane-permeant derivatives of mannose-1-phosphate.

2. A signalling pathway controlling c-Myc degradation that impacts oncogenic transformation of human cells.

3. Enzymatic and cellular study of a serotonin N-acetyltransferase phosphopantetheine-based prodrug.

4. The essential mitotic peptidyl-prolyl isomerase Pin1 binds and regulates mitosis-specific phosphoproteins.

5. Cyclophilin Inhibition by a (Z)-Alkene cis-Proline Mimic.

6. Prevalent overexpression of prolyl isomerase Pin1 in human cancers.

7. Design, synthesis, and biological evaluation of indolequinone phosphoramidate prodrugs targeted to DT-diaphorase.

8. Serine-cis-proline and serine-trans-proline isosteres: stereoselective synthesis of (Z)- and (E)-alkene mimics by Still-Wittig and Ireland-Claisen rearrangements.

9. Mononucleoside phosphotriester derivatives with S-acyl-2-thioethyl bioreversible phosphate-protecting groups: intracellular delivery of 3'-azido-2',3'-dideoxythymidine 5'-monophosphate.

10. Structural basis for high-affinity peptide inhibition of human Pin1.

1. A reduced-amide inhibitor of Pin1 binds in a conformation resembling a twisted-amide transition state.

2. Synthesis of a phosphoserine mimetic prodrug with potent 14-3-3 protein inhibitory activity.

3. 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.

4. A Phosphoramidate Strategy Enables Membrane Permeability of a Non-nucleotide Inhibitor of the Prolyl Isomerase Pin1.

Review 5. Prolyl isomerases in gene transcription.

6. Molecular basis for an ancient partnership between prolyl isomerase Pin1 and phosphatase inhibitor-2.

7. Cyclic cis-Locked Phospho-Dipeptides Reduce Entry of AβPP into Amyloidogenic Processing Pathway.

Review 8. The Ess1 prolyl isomerase: traffic cop of the RNA polymerase II transcription cycle.

9. Convergent synthesis of alpha-ketoamide inhibitors of Pin1.

10. Cyclohexyl ketone inhibitors of Pin1 dock in a trans-diaxial cyclohexane conformation.