Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas.


Journal

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

Informations de publication

Date de publication:
18 Dec 2019
Historique:
entrez: 14 6 2021
pubmed: 18 12 2019
medline: 18 12 2019
Statut: epublish

Résumé

Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues.

Identifiants

pubmed: 34123261
doi: 10.1039/c9sc05558d
pii: c9sc05558d
pmc: PMC8148049
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1368-1374

Subventions

Organisme : European Research Council
ID : 771443
Pays : International

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

The authors declare no conflicts of interest.

Références

Chem Commun (Camb). 2012 Jul 28;48(59):7401-3
pubmed: 22715465
Angew Chem Int Ed Engl. 2019 Nov 18;58(47):16894-16898
pubmed: 31535788
J Am Chem Soc. 2016 Jan 13;138(1):402-7
pubmed: 26684612
J Biophotonics. 2012 Nov;5(11-12):815-26
pubmed: 23132668
Chem Commun (Camb). 2011 Oct 21;47(39):10939-41
pubmed: 21909540
J Am Chem Soc. 2018 Nov 21;140(46):15820-15826
pubmed: 30380856
Nature. 2011 Jun 08;475(7355):222-5
pubmed: 21654748
Oncogene. 2011 Jan 13;30(2):127-38
pubmed: 20890307
J Org Chem. 2013 Aug 16;78(16):8129-35
pubmed: 23865986
Histochem Cell Biol. 2008 Jun;129(6):705-33
pubmed: 18461349
Am J Med. 2013 Jun;126(6):472-9
pubmed: 23561631
Org Biomol Chem. 2016 Sep 26;14(38):8911-8921
pubmed: 27714204
Chem Sci. 2015 Feb 1;6(2):1150-1158
pubmed: 29560202
Chem Sci. 2019 Jun 21;10(29):6944-6956
pubmed: 31588261
Mol Pharm. 2017 Mar 6;14(3):593-604
pubmed: 28157321
J Med Chem. 2017 Jun 22;60(12):4893-4903
pubmed: 28520410
J Oncol. 2012;2012:438647
pubmed: 22848217
Cell. 2010 Apr 2;141(1):39-51
pubmed: 20371344
Chem Commun (Camb). 2014 May 11;50(36):4714-6
pubmed: 24676233
Chem Sci. 2018 Nov 27;10(6):1619-1625
pubmed: 30842824
J Am Chem Soc. 2014 Dec 31;136(52):17942-5
pubmed: 25495860
J Med Chem. 2014 Oct 23;57(20):8530-9
pubmed: 25275946
Curr Opin Pharmacol. 2010 Oct;10(5):571-7
pubmed: 20598638
Front Oncol. 2017 Dec 22;7:314
pubmed: 29312886
Nat Rev Clin Oncol. 2016 Nov;13(11):674-690
pubmed: 27184417
Proc Natl Acad Sci U S A. 2010 Mar 2;107(9):4317-22
pubmed: 20160097
Chem Commun (Camb). 2017 Jan 10;53(5):945-948
pubmed: 28009021
J Med Chem. 2009 Apr 23;52(8):2363-71
pubmed: 19296650
Bioconjug Chem. 2012 Dec 19;23(12):2434-43
pubmed: 23153224
J Org Chem. 2019 Mar 1;84(5):2879-2890
pubmed: 30726078
Chem Commun (Camb). 2009 Aug 14;(30):4515-7
pubmed: 19617968
Chem Sci. 2019 Aug 20;10(40):9351-9357
pubmed: 32110299
Nat Rev Cancer. 2005 Aug;5(8):591-602
pubmed: 16056258
Nat Commun. 2016 Mar 09;7:10940
pubmed: 26956772
Chemistry. 2009 Sep 21;15(37):9394-403
pubmed: 19575348
Arch Biochem Biophys. 2019 Jan;661:187-195
pubmed: 30465736
Nat Rev Immunol. 2015 Feb;15(2):73-86
pubmed: 25614318
Chem Soc Rev. 2015 Jul 21;44(14):4953-72
pubmed: 25801415
Chem Rev. 2012 Aug 8;112(8):4391-420
pubmed: 22616565
Chem Commun (Camb). 2011 Aug 7;47(29):8424-6
pubmed: 21701752
Angew Chem Int Ed Engl. 2017 Mar 27;56(14):3758-3769
pubmed: 27907246
Stem Cell Res. 2014 May;12(3):730-41
pubmed: 24727632
J Invest Dermatol. 2017 Jan;137(1):142-150
pubmed: 27595935
Nat Protoc. 2017 Aug;12(8):1588-1619
pubmed: 28703788
ACS Cent Sci. 2017 Sep 27;3(9):995-1005
pubmed: 28979941

Auteurs

Ramon Subiros-Funosas (R)

Centre for Inflammation Research, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK marc.vendrell@ed.ac.uk.

Vivian Cheuk Lam Ho (VCL)

Centre for Inflammation Research, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK marc.vendrell@ed.ac.uk.

Nicole D Barth (ND)

Centre for Inflammation Research, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK marc.vendrell@ed.ac.uk.

Lorena Mendive-Tapia (L)

Centre for Inflammation Research, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK marc.vendrell@ed.ac.uk.

Morena Pappalardo (M)

Laboratory of Physical Chemistry, Facultat de Farmàcia, Universitat de Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Av. Joan XXIII s/n 08028 Barcelona Spain.

Xavier Barril (X)

Laboratory of Physical Chemistry, Facultat de Farmàcia, Universitat de Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Av. Joan XXIII s/n 08028 Barcelona Spain.

Ruoyu Ma (R)

MRC Centre for Reproductive Health, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK.

Cheng-Bin Zhang (CB)

MRC Centre for Reproductive Health, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK.

Bin-Zhi Qian (BZ)

MRC Centre for Reproductive Health, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK.

Miquel Sintes (M)

Laboratory of Medicinal Chemistry, Faculty of Pharmacy, University of Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Avda Joan XXIII 27-30 Barcelona 08028 Spain rlavilla@ub.edu.

Ouldouz Ghashghaei (O)

Laboratory of Medicinal Chemistry, Faculty of Pharmacy, University of Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Avda Joan XXIII 27-30 Barcelona 08028 Spain rlavilla@ub.edu.

Rodolfo Lavilla (R)

Laboratory of Medicinal Chemistry, Faculty of Pharmacy, University of Barcelona and Institut de Biomedicina de la Universitat de Barcelona (IBUB) Avda Joan XXIII 27-30 Barcelona 08028 Spain rlavilla@ub.edu.

Marc Vendrell (M)

Centre for Inflammation Research, University of Edinburgh 47 Little France Crescent EH16 4TJ Edinburgh UK marc.vendrell@ed.ac.uk.

Classifications MeSH