Literature DB >> 17560105

Bicyclo[2.2.2]octanes: close structural mimics of the nuclear receptor-binding motif of steroid receptor coactivators.

Hai-Bing Zhou1, Margaret L Collins, Jillian R Gunther, John S Comninos, John A Katzenellenbogen.   

Abstract

Nuclear hormone receptor (NR) function relies on association of agonist-bound receptors with steroid receptor coactivator (SRC) proteins through a small pentapeptide motif (LXXLL) of the SRC that binds to a hydrophobic groove on the NR. We have synthesized a series of bicyclo[2.2.2]octanes that are close structural mimics of the two key leucine residues of this SRC sequence as bound in the hydrophobic groove of the estrogen receptor. These bicyclic systems block the NR-SRC interaction with modest potency.

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Year:  2007        PMID： 17560105      PMCID： PMC3216840          DOI： 10.1016/j.bmcl.2007.05.058

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


  28 in total

1.  Remarkably high asymmetric amplification in the chiral lanthanide complex-catalyzed hetero-Diels-Alder reaction: first example of the nonlinear effect in ML3 system

Authors: 
Journal:  Org Lett       Date:  2000-01       Impact factor: 6.005

2.  Identification of small-molecule inhibitors of interaction between the BH3 domain and Bcl-xL.

Authors:  A Degterev; A Lugovskoy; M Cardone; B Mulley; G Wagner; T Mitchison; J Yuan
Journal:  Nat Cell Biol       Date:  2001-02       Impact factor: 28.824

Review 3.  Combinatorial control of gene expression by nuclear receptors and coregulators.

Authors:  Neil J McKenna; Bert W O'Malley
Journal:  Cell       Date:  2002-02-22       Impact factor: 41.582

4.  Design and application of an alpha-helix-mimetic scaffold based on an oligoamide-foldamer strategy: antagonism of the Bak BH3/Bcl-xL complex.

Authors:  Justin T Ernst; Jorge Becerril; Hyung Soon Park; Hang Yin; Andrew D Hamilton
Journal:  Angew Chem Int Ed Engl       Date:  2003-02-03       Impact factor: 15.336

5.  Molecular basis of agonism and antagonism in the oestrogen receptor.

Authors:  A M Brzozowski; A C Pike; Z Dauter; R E Hubbard; T Bonn; O Engström; L Ohman; G L Greene; J A Gustafsson; M Carlquist
Journal:  Nature       Date:  1997-10-16       Impact factor: 49.962

6.  Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine.

Authors:  E J Corey; Takanori Shibata; Thomas W Lee
Journal:  J Am Chem Soc       Date:  2002-04-17       Impact factor: 15.419

7.  Small molecule RITA binds to p53, blocks p53-HDM-2 interaction and activates p53 function in tumors.

Authors:  Natalia Issaeva; Przemyslaw Bozko; Martin Enge; Marina Protopopova; Lisette G G C Verhoef; Maria Masucci; Aladdin Pramanik; Galina Selivanova
Journal:  Nat Med       Date:  2004-11-21       Impact factor: 53.440

8.  Design, synthesis, and in vitro biological evaluation of small molecule inhibitors of estrogen receptor alpha coactivator binding.

Authors:  Alice L Rodriguez; Anobel Tamrazi; Margaret L Collins; John A Katzenellenbogen
Journal:  J Med Chem       Date:  2004-01-29       Impact factor: 7.446

9.  The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen.

Authors:  A K Shiau; D Barstad; P M Loria; L Cheng; P J Kushner; D A Agard; G L Greene
Journal:  Cell       Date:  1998-12-23       Impact factor: 41.582

10.  Thioether side chain cyclization for helical peptide formation: inhibitors of estrogen receptor-coactivator interactions.

Authors:  A K Galande; K S Bramlett; T P Burris; J L Wittliff; A F Spatola
Journal:  J Pept Res       Date:  2004-03
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  14 in total

1.  Synthesis of a tetrasubstituted tetrahydronaphthalene scaffold for α-helix mimicry via a MgBr2-catalyzed Friedel-Crafts epoxide cycloalkylation.

Authors:  Devan Naduthambi; Santosh Bhor; Michael B Elbaum; Neal J Zondlo
Journal:  Org Lett       Date:  2013-09-09       Impact factor: 6.005

2.  The 2010 Philip S. Portoghese Medicinal Chemistry Lectureship: addressing the "core issue" in the design of estrogen receptor ligands.

Authors:  John A Katzenellenbogen
Journal:  J Med Chem       Date:  2011-07-11       Impact factor: 7.446

Review 3.  Nuclear receptor coregulators as a new paradigm for therapeutic targeting.

Authors:  Elaine Y Hsia; Michael L Goodson; June X Zou; Martin L Privalsky; Hong-Wu Chen
Journal:  Adv Drug Deliv Rev       Date:  2010-10-07       Impact factor: 15.470

4.  Alternative inhibition of androgen receptor signaling: peptidomimetic pyrimidines as direct androgen receptor/coactivator disruptors.

Authors:  Jillian R Gunther; Alexander A Parent; John A Katzenellenbogen
Journal:  ACS Chem Biol       Date:  2009-06-19       Impact factor: 5.100

Review 5.  Minireview: Not picking pockets: nuclear receptor alternate-site modulators (NRAMs).

Authors:  Terry W Moore; Christopher G Mayne; John A Katzenellenbogen
Journal:  Mol Endocrinol       Date:  2009-11-20

6.  Blocking estrogen signaling after the hormone: pyrimidine-core inhibitors of estrogen receptor-coactivator binding.

Authors:  Alexander A Parent; Jillian R Gunther; John A Katzenellenbogen
Journal:  J Med Chem       Date:  2008-09-12       Impact factor: 7.446

7.  Amphipathic benzenes are designed inhibitors of the estrogen receptor alpha/steroid receptor coactivator interaction.

Authors:  Jillian R Gunther; Terry W Moore; Margaret L Collins; John A Katzenellenbogen
Journal:  ACS Chem Biol       Date:  2008-05-16       Impact factor: 5.100

8.  A set of time-resolved fluorescence resonance energy transfer assays for the discovery of inhibitors of estrogen receptor-coactivator binding.

Authors:  Jillian R Gunther; Yuhong Du; Eric Rhoden; Iestyn Lewis; Brian Revennaugh; Terry W Moore; Sung Hoon Kim; Raymond Dingledine; Haian Fu; John A Katzenellenbogen
Journal:  J Biomol Screen       Date:  2009-02-04

9.  In silico discovery and validation of potent small-molecule inhibitors targeting the activation function 2 site of human oestrogen receptor α.

Authors:  Kriti Singh; Ravi Shashi Nayana Munuganti; Eric Leblanc; Yu Lun Lin; Euphemia Leung; Nada Lallous; Miriam Butler; Artem Cherkasov; Paul S Rennie
Journal:  Breast Cancer Res       Date:  2015-02-25       Impact factor: 6.466

10.  LXXLL peptide converts transportan 10 to a potent inducer of apoptosis in breast cancer cells.

Authors:  Kairit Tints; Madis Prink; Toomas Neuman; Kaia Palm
Journal:  Int J Mol Sci       Date:  2014-04-03       Impact factor: 5.923
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