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Literature DB >> 19435295

Design, synthesis, and biological evaluation of conformationally constrained cis-amide Hsp90 inhibitors.

Adam S Duerfeldt¹, Gary E L Brandt, Brian S J Blagg.

Abstract

Conformationally constrained cis-amide chimeric inhibitors of Hsp90 have been synthesized and evaluated for their Hsp90 inhibitory activity. These new compounds exhibited Hsp90 ATPase inhibition and induced Hsp90-dependent client protein degradation in a dose-dependent manner. Biological data reported herein suggests that amide bond isomerization of geldanamycin derivatives plays an important role in affinity for the heteroprotein complex present in cancer cells.

Entities: CellLine Chemical Disease Gene Species

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Year: 2009 PMID： 19435295 PMCID： PMC2697668 DOI： 10.1021/ol900783m

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

27 in total

1. Heat shock protein-chaperoned peptides but not free peptides introduced into the cytosol are presented efficiently by major histocompatibility complex I molecules.

Authors: R J Binder; N E Blachere; P K Srivastava
Journal: J Biol Chem Date: 2001-03-08 Impact factor: 5.157

Review 2. The hallmarks of cancer.

Authors: D Hanahan; R A Weinberg
Journal: Cell Date: 2000-01-07 Impact factor: 41.582

3. Coordinated ATP hydrolysis by the Hsp90 dimer.

Authors: K Richter; P Muschler; O Hainzl; J Buchner
Journal: J Biol Chem Date: 2001-07-05 Impact factor: 5.157

Review 4. Molecular chaperones--cellular machines for protein folding.

Authors: Stefan Walter; Johannes Buchner
Journal: Angew Chem Int Ed Engl Date: 2002-04-02 Impact factor: 15.336

5. Optimizing natural products by biosynthetic engineering: discovery of nonquinone Hsp90 inhibitors.

Authors: Ming-Qiang Zhang; Sabine Gaisser; Mohammad Nur-E-Alam; Lesley S Sheehan; William A Vousden; Nikolaos Gaitatzis; Gerrard Peck; Nigel J Coates; Steven J Moss; Markus Radzom; Teresa A Foster; Rose M Sheridan; Matthew A Gregory; S Mark Roe; Chrisostomos Prodromou; Laurence Pearl; Susan M Boyd; Barrie Wilkinson; Christine J Martin
Journal: J Med Chem Date: 2008-09-25 Impact factor: 7.446

6. 17AAG: low target binding affinity and potent cell activity--finding an explanation.

Authors: Gabriela Chiosis; Henri Huezo; Neal Rosen; Edward Mimnaugh; Luke Whitesell; Len Neckers
Journal: Mol Cancer Ther Date: 2003-02 Impact factor: 6.261

Review 7. HSP90 as a new therapeutic target for cancer therapy: the story unfolds.

Authors: Alison Maloney; Paul Workman
Journal: Expert Opin Biol Ther Date: 2002-01 Impact factor: 4.388

8. Quantum chemical calculations and mutational analysis suggest heat shock protein 90 catalyzes trans-cis isomerization of geldanamycin.

Authors: Yong-Sok Lee; Monica G Marcu; Len Neckers
Journal: Chem Biol Date: 2004-07

9. A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors.

Authors: Adeela Kamal; Lia Thao; John Sensintaffar; Lin Zhang; Marcus F Boehm; Lawrence C Fritz; Francis J Burrows
Journal: Nature Date: 2003-09-25 Impact factor: 49.962

10. Inhibition of heat shock protein HSP90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: essential role for stress proteins in oncogenic transformation.

Authors: L Whitesell; E G Mimnaugh; B De Costa; C E Myers; L M Neckers
Journal: Proc Natl Acad Sci U S A Date: 1994-08-30 Impact factor: 11.205

9 in total

1. A mechanistic and structural analysis of the inhibition of the 90-kDa heat shock protein by the benzoquinone and hydroquinone ansamycins.

Authors: Philip Reigan; David Siegel; Wenchang Guo; David Ross
Journal: Mol Pharmacol Date: 2011-02-01 Impact factor: 4.436

2. Scalable and chromatography-free synthesis of 2-(2-formylalkyl)arenecarboxylic acid derivatives through the supramolecularly controlled hydroformylation of vinylarene-2-carboxylic acids.

Authors: Paweł Dydio; Joost N H Reek
Journal: Nat Protoc Date: 2014-04-24 Impact factor: 13.491

Design, synthesis, and biological evaluation of conformationally constrained cis-amide Hsp90 inhibitors.

1. Heat shock protein-chaperoned peptides but not free peptides introduced into the cytosol are presented efficiently by major histocompatibility complex I molecules.

Review 2. The hallmarks of cancer.

3. Coordinated ATP hydrolysis by the Hsp90 dimer.

Review 4. Molecular chaperones--cellular machines for protein folding.

5. Optimizing natural products by biosynthetic engineering: discovery of nonquinone Hsp90 inhibitors.

6. 17AAG: low target binding affinity and potent cell activity--finding an explanation.

Review 7. HSP90 as a new therapeutic target for cancer therapy: the story unfolds.

8. Quantum chemical calculations and mutational analysis suggest heat shock protein 90 catalyzes trans-cis isomerization of geldanamycin.

9. A high-affinity conformation of Hsp90 confers tumour selectivity on Hsp90 inhibitors.

10. Inhibition of heat shock protein HSP90-pp60v-src heteroprotein complex formation by benzoquinone ansamycins: essential role for stress proteins in oncogenic transformation.

1. A mechanistic and structural analysis of the inhibition of the 90-kDa heat shock protein by the benzoquinone and hydroquinone ansamycins.

2. Scalable and chromatography-free synthesis of 2-(2-formylalkyl)arenecarboxylic acid derivatives through the supramolecularly controlled hydroformylation of vinylarene-2-carboxylic acids.

3. Development of radamide analogs as Grp94 inhibitors.

4. Pharmacological tuning of heat shock protein 70 modulates polyglutamine toxicity and aggregation.

Review 5. Natural Product Inspired N-Terminal Hsp90 Inhibitors: From Bench to Bedside?

Review 6. Alternate strategies of Hsp90 modulation for the treatment of cancer and other diseases.

7. Design, synthesis, and biological activity of bicyclic radester analogues as Hsp90 inhibitors.

Review 8. Proteostasis In The Endoplasmic Reticulum: Road to Cure.

9. A domino reaction for generating β-aryl aldehydes from alkynes by substrate recognition catalysis.