Literature DB >> 29725689

A "cross-stitched" peptide with improved helicity and proteolytic stability.

Thomas E Speltz1, Christopher G Mayne, Sean W Fanning, Zamia Siddiqui, Emad Tajkhorshid, Geoffrey L Greene, Terry W Moore.   

Abstract

A new computational approach to obtain quantitative energy profiles for helix folding was used in the design of orthogonal hydrocarbon and lactam bicyclic peptides. The proteolytically stable, "cross-stitched" peptide SRC2-BCP1 shows nanomolar affinity for estrogen receptor α and X-ray crystallography confirms a helical binding pose.

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Year:  2018        PMID： 29725689      PMCID： PMC5993042          DOI： 10.1039/c8ob00790j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  26 in total

1.  A precisely positioned chiral center in an i, i + 7 tether modulates the helicity of the backbone peptide.

Authors:  Kuan Hu; Chengjie Sun; Dan Yang; Yujie Wu; Chuan Shi; Longjian Chen; Tao Liao; Jialin Guo; Yinghuan Liu; Zigang Li
Journal:  Chem Commun (Camb)       Date:  2017-06-20       Impact factor: 6.222

2.  Stitched α-helical peptides via bis ring-closing metathesis.

Authors:  Gerard J Hilinski; Young-Woo Kim; Jooyeon Hong; Peter S Kutchukian; Charisse M Crenshaw; Shaunna S Berkovitch; Andrew Chang; Sihyun Ham; Gregory L Verdine
Journal:  J Am Chem Soc       Date:  2014-08-21       Impact factor: 15.419

Review 3.  Peptide stapling techniques based on different macrocyclisation chemistries.

Authors:  Yu Heng Lau; Peterson de Andrade; Yuteng Wu; David R Spring
Journal:  Chem Soc Rev       Date:  2014-09-08       Impact factor: 54.564

4.  A Cell-Permeable Stapled Peptide Inhibitor of the Estrogen Receptor/Coactivator Interaction.

Authors:  Thomas E Speltz; Jeanne M Danes; Joshua D Stender; Jonna Frasor; Terry W Moore
Journal:  ACS Chem Biol       Date:  2018-01-24       Impact factor: 5.100

5.  Estrogen receptor coregulator binding modulators (ERXs) effectively target estrogen receptor positive human breast cancers.

Authors:  Ganesh V Raj; Gangadhara Reddy Sareddy; Shihong Ma; Tae-Kyung Lee; Suryavathi Viswanadhapalli; Rui Li; Xihui Liu; Shino Murakami; Chien-Cheng Chen; Wan-Ru Lee; Monica Mann; Samaya Rajeshwari Krishnan; Bikash Manandhar; Vijay K Gonugunta; Douglas Strand; Rajeshwar Rao Tekmal; Jung-Mo Ahn; Ratna K Vadlamudi
Journal:  Elife       Date:  2017-08-08       Impact factor: 8.140

6.  Structural Basis of Inhibition of ERα-Coactivator Interaction by High-Affinity N-Terminus Isoaspartic Acid Tethered Helical Peptides.

Authors:  Mingsheng Xie; Hui Zhao; Qisong Liu; Yujia Zhu; Feng Yin; Yujie Liang; Yanhong Jiang; Dongyuan Wang; Kuan Hu; Xuan Qin; Zichen Wang; Yujie Wu; Naihan Xu; Xiyang Ye; Tao Wang; Zigang Li
Journal:  J Med Chem       Date:  2017-10-31       Impact factor: 7.446

7.  Hydrocarbon double-stapling remedies the proteolytic instability of a lengthy peptide therapeutic.

Authors:  Gregory H Bird; Navid Madani; Alisa F Perry; Amy M Princiotto; Jeffrey G Supko; Xiaoying He; Evripidis Gavathiotis; Joseph G Sodroski; Loren D Walensky
Journal:  Proc Natl Acad Sci U S A       Date:  2010-07-21       Impact factor: 11.205

8.  Energetic contribution of solvent-exposed ion pairs to alpha-helix structure.

Authors:  P C Lyu; P J Gans; N R Kallenbach
Journal:  J Mol Biol       Date:  1992-01-05       Impact factor: 5.469

9.  Stapled α-helical peptide drug development: a potent dual inhibitor of MDM2 and MDMX for p53-dependent cancer therapy.

Authors:  Yong S Chang; Bradford Graves; Vincent Guerlavais; Christian Tovar; Kathryn Packman; Kwong-Him To; Karen A Olson; Kamala Kesavan; Pranoti Gangurde; Aditi Mukherjee; Theresa Baker; Krzysztof Darlak; Carl Elkin; Zoran Filipovic; Farooq Z Qureshi; Hongliang Cai; Pamela Berry; Eric Feyfant; Xiangguo E Shi; James Horstick; D Allen Annis; Anthony M Manning; Nader Fotouhi; Huw Nash; Lyubomir T Vassilev; Tomi K Sawyer
Journal:  Proc Natl Acad Sci U S A       Date:  2013-08-14       Impact factor: 11.205

10.  Crystal structures of stapled and hydrogen bond surrogate peptides targeting a fully buried protein-helix interaction.

Authors:  Christopher H Douse; Sabrina J Maas; Jemima C Thomas; James A Garnett; Yunyun Sun; Ernesto Cota; Edward W Tate
Journal:  ACS Chem Biol       Date:  2014-08-06       Impact factor: 5.100
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  3 in total

Review 1.  Steroid receptor/coactivator binding inhibitors: An update.

Authors:  Kornelia J Skowron; Kenneth Booker; Changfeng Cheng; Simone Creed; Brian P David; Phillip R Lazzara; Amy Lian; Zamia Siddiqui; Thomas E Speltz; Terry W Moore
Journal:  Mol Cell Endocrinol       Date:  2019-06-01       Impact factor: 4.102

2.  Versatile Peptide Macrocyclization with Diels-Alder Cycloadditions.

Authors:  Jeffrey E Montgomery; Justin A Donnelly; Sean W Fanning; Thomas E Speltz; Xianghang Shangguan; John S Coukos; Geoffrey L Greene; Raymond E Moellering
Journal:  J Am Chem Soc       Date:  2019-09-26       Impact factor: 15.419

3.  Backbone distortions in lactam-bridged helical peptides.

Authors:  Ali Moazzam; Vesna Stanojlovic; Arthur Hinterholzer; Christoph Holzner; Cornelia Roschger; Andreas Zierer; Markus Wiederstein; Mario Schubert; Chiara Cabrele
Journal:  J Pept Sci       Date:  2022-02-09       Impact factor: 2.408
  3 in total

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