Macrocyclization of an all-d linear α-helical peptide imparts cellular permeability.


Journal

Chemical science
ISSN: 2041-6520
Titre abrégé: Chem Sci
Pays: England
ID NLM: 101545951

Informations de publication

Date de publication:
07 Jun 2020
Historique:
received: 17 12 2019
accepted: 08 05 2020
entrez: 3 9 2020
pubmed: 3 9 2020
medline: 3 9 2020
Statut: epublish

Résumé

Peptide-based molecules hold great potential as targeted inhibitors of intracellular protein-protein interactions (PPIs). Indeed, the vast diversity of chemical space conferred through their primary, secondary and tertiary structures allows these molecules to be applied to targets that are typically deemed intractable

Identifiants

pubmed: 32874502
doi: 10.1039/c9sc06383h
pii: c9sc06383h
pmc: PMC7441689
doi:

Types de publication

Journal Article

Langues

eng

Pagination

5577-5591

Informations de copyright

This journal is © The Royal Society of Chemistry 2020.

Références

Cell Rep. 2014 Dec 11;9(5):1946-1958
pubmed: 25464845
Angew Chem Int Ed Engl. 2017 Aug 21;56(35):10294-10323
pubmed: 28186380
Angew Chem Int Ed Engl. 2014 Feb 24;53(9):2498-503
pubmed: 24481744
Proc Natl Acad Sci U S A. 2010 Aug 10;107(32):14321-6
pubmed: 20660730
Chem Sci. 2018 Apr 25;9(20):4638-4643
pubmed: 29899957
Proc Natl Acad Sci U S A. 2018 Jan 30;115(5):E886-E895
pubmed: 29339518
ACS Chem Biol. 2013 Mar 15;8(3):506-12
pubmed: 23214419
Bioorg Med Chem. 2018 Jun 1;26(10):2807-2815
pubmed: 29598901
Mol Cell. 2006 Oct 20;24(2):199-210
pubmed: 17052454
Nat Rev Drug Discov. 2016 Aug;15(8):533-50
pubmed: 27050677
ACS Chem Biol. 2016 Apr 15;11(4):1058-65
pubmed: 26745345
Proc Natl Acad Sci U S A. 2013 Sep 3;110(36):E3445-54
pubmed: 23946421
J Am Chem Soc. 2007 Mar 7;129(9):2456-7
pubmed: 17284038
BMC Biol. 2017 Nov 09;15(1):108
pubmed: 29121928
Drug Discov Today. 2016 Oct;21(10):1642-1653
pubmed: 27326912
Chem Sci. 2019 Jan 7;10(8):2489-2500
pubmed: 30881679
Cell Chem Biol. 2017 Aug 17;24(8):958-968.e5
pubmed: 28757184
J Med Chem. 2012 Jul 12;55(13):6237-41
pubmed: 22694121
Oncotarget. 2012 Mar;3(3):228-35
pubmed: 22410433
J Virol. 2010 Nov;84(21):11235-44
pubmed: 20719956
J Med Chem. 2012 Feb 9;55(3):1137-46
pubmed: 22196480
Annu Rev Pathol. 2016 May 23;11:617-44
pubmed: 27022975
J Med Chem. 2017 Nov 9;60(21):8731-8740
pubmed: 29045135
Bioorg Med Chem. 2018 Jun 1;26(10):2700-2707
pubmed: 28720325
Comput Struct Biotechnol J. 2019 Feb 19;17:263-281
pubmed: 30867891
J Med Chem. 2018 Feb 22;61(4):1382-1414
pubmed: 28737935
J Hematol Oncol. 2017 Jul 3;10(1):133
pubmed: 28673313
Proc Natl Acad Sci U S A. 2010 Aug 10;107(32):14093-8
pubmed: 20660316
J Biol Chem. 2016 Aug 26;291(35):18310-25
pubmed: 27334922
Nat Rev Drug Discov. 2018 Jul 30;17(8):531-533
pubmed: 30057410
Angew Chem Int Ed Engl. 2010 May 10;49(21):3649-52
pubmed: 20449836
J Am Chem Soc. 2014 Sep 3;136(35):12314-22
pubmed: 25105213
Front Oncol. 2016 Jan 27;6:7
pubmed: 26858935
Nature. 1992 Jul 2;358(6381):15-6
pubmed: 1614522
Mol Ther. 2016 Apr;24(4):707-18
pubmed: 26675501
J Am Chem Soc. 2017 Jun 14;139(23):7792-7802
pubmed: 28414223
Antimicrob Agents Chemother. 2017 Mar 24;61(4):
pubmed: 28137809
Chembiochem. 2010 Oct 18;11(15):2104-7
pubmed: 20821791
J Clin Invest. 2014 May;124(5):2113-24
pubmed: 24743147
J Am Chem Soc. 2017 Feb 15;139(6):2245-2256
pubmed: 28084734
J Am Chem Soc. 2019 Mar 13;141(10):4167-4181
pubmed: 30768253
Org Biomol Chem. 2018 May 23;16(20):3702-3706
pubmed: 29725689
J Comput Chem. 2014 Jan 15;35(2):150-8
pubmed: 24318649
J Med Chem. 2014 Aug 14;57(15):6275-88
pubmed: 24601557
ACS Chem Biol. 2014 Mar 21;9(3):831-7
pubmed: 24358963
Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11760-4
pubmed: 26259671
Exp Hematol. 2016 Sep;44(9):791-798
pubmed: 27327543
Bioorg Med Chem. 2015 Mar 1;23(5):1055-61
pubmed: 25637122
J Med Chem. 2016 Oct 27;59(20):9503-9512
pubmed: 27690434
Expert Opin Drug Discov. 2017 Nov;12(11):1117-1125
pubmed: 28889766
Proteins. 2007 Feb 15;66(3):697-706
pubmed: 17120231
ACS Chem Biol. 2016 Aug 19;11(8):2375-82
pubmed: 27336832
J Phys Chem Lett. 2016 Sep 1;7(17):3452-7
pubmed: 27532490
Angew Chem Int Ed Engl. 2017 Jan 9;56(2):524-529
pubmed: 27918136
ACS Chem Biol. 2013 Feb 15;8(2):297-302
pubmed: 23151250
Chem Sci. 2019 May 30;10(26):6457-6466
pubmed: 31316744
Chem Commun (Camb). 2015 Feb 25;51(16):3302-15
pubmed: 25578807
Proc Natl Acad Sci U S A. 2018 Feb 13;115(7):1505-1510
pubmed: 29378946
Chembiochem. 2016 Sep 2;17(17):1643-51
pubmed: 27465925

Auteurs

Srinivasaraghavan Kannan (S)

Bioinformatics Institute , Agency for Science, Technology and Research (ASTAR) , 30 Biopolis Street, #07-01 Matrix , Singapore 138671 , Singapore . Email: raghavk@bii.a-star.edu.sg ; Email: chandra@bii.a-star.edu.sg ; ; Tel: +65 6478 8353 ; Tel: +65 6478 8273.

Pietro G A Aronica (PGA)

Bioinformatics Institute , Agency for Science, Technology and Research (ASTAR) , 30 Biopolis Street, #07-01 Matrix , Singapore 138671 , Singapore . Email: raghavk@bii.a-star.edu.sg ; Email: chandra@bii.a-star.edu.sg ; ; Tel: +65 6478 8353 ; Tel: +65 6478 8273.

Simon Ng (S)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Dawn Thean Gek Lian (DT)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Yuri Frosi (Y)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Sharon Chee (S)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Jiang Shimin (J)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Tsz Ying Yuen (TY)

Institute of Chemical & Engineering Science , Agency for Science, Technology and Research (ASTAR) , 8 Biomedical Grove, #07, Neuros Building , Singapore 138665.

Ahmad Sadruddin (A)

MSD International , Translation Medicine Research Centre , 8 Biomedical Grove, #04-01/05 Neuros Building , Singapore , 138665 , Singapore . Email: anthony_partridge@merck.com.

Hung Yi Kristal Kaan (HYK)

MSD International , Translation Medicine Research Centre , 8 Biomedical Grove, #04-01/05 Neuros Building , Singapore , 138665 , Singapore . Email: anthony_partridge@merck.com.

Arun Chandramohan (A)

MSD International , Translation Medicine Research Centre , 8 Biomedical Grove, #04-01/05 Neuros Building , Singapore , 138665 , Singapore . Email: anthony_partridge@merck.com.

Jin Huei Wong (JH)

Bioinformatics Institute , Agency for Science, Technology and Research (ASTAR) , 30 Biopolis Street, #07-01 Matrix , Singapore 138671 , Singapore . Email: raghavk@bii.a-star.edu.sg ; Email: chandra@bii.a-star.edu.sg ; ; Tel: +65 6478 8353 ; Tel: +65 6478 8273.

Yaw Sing Tan (YS)

Bioinformatics Institute , Agency for Science, Technology and Research (ASTAR) , 30 Biopolis Street, #07-01 Matrix , Singapore 138671 , Singapore . Email: raghavk@bii.a-star.edu.sg ; Email: chandra@bii.a-star.edu.sg ; ; Tel: +65 6478 8353 ; Tel: +65 6478 8273.

Zi Wei Chang (ZW)

Singapore Immunology Network (SIgN) , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #03-06, Immunos , Singapore 138648.

Fernando J Ferrer-Gago (FJ)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Prakash Arumugam (P)

Bioinformatics Institute , Agency for Science, Technology and Research (ASTAR) , 30 Biopolis Street, #07-01 Matrix , Singapore 138671 , Singapore . Email: raghavk@bii.a-star.edu.sg ; Email: chandra@bii.a-star.edu.sg ; ; Tel: +65 6478 8353 ; Tel: +65 6478 8273.

Yi Han (Y)

Merck & Co., Inc. , Kenilworth , New Jersey , USA.

Shiying Chen (S)

Merck & Co., Inc. , Kenilworth , New Jersey , USA.

Laurent Rénia (L)

Singapore Immunology Network (SIgN) , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #03-06, Immunos , Singapore 138648.

Christopher J Brown (CJ)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Charles W Johannes (CW)

Institute of Chemical & Engineering Science , Agency for Science, Technology and Research (ASTAR) , 8 Biomedical Grove, #07, Neuros Building , Singapore 138665.

Brian Henry (B)

MSD International , Translation Medicine Research Centre , 8 Biomedical Grove, #04-01/05 Neuros Building , Singapore , 138665 , Singapore . Email: anthony_partridge@merck.com.

David P Lane (DP)

p53 Laboratory , Agency for Science, Technology and Research (ASTAR) , 8A Biomedical Grove, #06-04/05, Neuros/Immunos , Singapore 138648.

Tomi K Sawyer (TK)

Merck & Co., Inc. , Boston , Massachusetts , USA.

Chandra S Verma (CS)

Bioinformatics Institute , Agency for Science, Technology and Research (ASTAR) , 30 Biopolis Street, #07-01 Matrix , Singapore 138671 , Singapore . Email: raghavk@bii.a-star.edu.sg ; Email: chandra@bii.a-star.edu.sg ; ; Tel: +65 6478 8353 ; Tel: +65 6478 8273.
School of Biological Sciences , Nanyang Technological University , 60 Nanyang Drive , Singapore 637551.
Department of Biological Sciences , National University of Singapore , 14 Science Drive 4 , Singapore 117543.

Anthony W Partridge (AW)

MSD International , Translation Medicine Research Centre , 8 Biomedical Grove, #04-01/05 Neuros Building , Singapore , 138665 , Singapore . Email: anthony_partridge@merck.com.

Classifications MeSH