Targeting fibroblast activation protein (FAP): next generation PET radiotracers using squaramide coupled bifunctional DOTA and DATA

DATA5m DOTA FAP Gallium-68 HT-29 PREP Squaramide Squaric acid

Journal

EJNMMI radiopharmacy and chemistry
ISSN: 2365-421X
Titre abrégé: EJNMMI Radiopharm Chem
Pays: England
ID NLM: 101714628

Informations de publication

Date de publication:
29 Jul 2020
Historique:
received: 02 06 2020
accepted: 15 07 2020
entrez: 31 7 2020
pubmed: 31 7 2020
medline: 31 7 2020
Statut: epublish

Résumé

Fibroblast activation protein (FAP) is a proline selective serine protease that is overexpressed in tumor stroma and in lesions of many other diseases that are characterized by tissue remodeling. In 2014, a most potent FAP-inhibitor (referred to as UAMC1110) with low nanomolar FAP-affinity and high selectivity toward related enzymes such as prolyl oligopeptidase (PREP) and the dipeptidyl-peptidases (DPPs): DPP4, DPP8/9 and DPP2 were developed. This inhibitor has been adopted recently by other groups to create radiopharmaceuticals by coupling bifunctional chelator-linker systems. Here, we report squaric acid (SA) containing bifunctional DATA [ In this work, novel PET radiotracers targeting fibroblast activation protein were synthesized and biochemically investigated. Critical substructures of the novel compounds are a squaramide linker unit derived from the basic motif of squaric acid, DOTA and DATA

Sections du résumé

BACKGROUND BACKGROUND
Fibroblast activation protein (FAP) is a proline selective serine protease that is overexpressed in tumor stroma and in lesions of many other diseases that are characterized by tissue remodeling. In 2014, a most potent FAP-inhibitor (referred to as UAMC1110) with low nanomolar FAP-affinity and high selectivity toward related enzymes such as prolyl oligopeptidase (PREP) and the dipeptidyl-peptidases (DPPs): DPP4, DPP8/9 and DPP2 were developed. This inhibitor has been adopted recently by other groups to create radiopharmaceuticals by coupling bifunctional chelator-linker systems. Here, we report squaric acid (SA) containing bifunctional DATA
RESULTS RESULTS
[
CONCLUSION CONCLUSIONS
In this work, novel PET radiotracers targeting fibroblast activation protein were synthesized and biochemically investigated. Critical substructures of the novel compounds are a squaramide linker unit derived from the basic motif of squaric acid, DOTA and DATA

Identifiants

pubmed: 32728930
doi: 10.1186/s41181-020-00102-z
pii: 10.1186/s41181-020-00102-z
pmc: PMC7391456
doi:

Types de publication

Journal Article

Langues

eng

Pagination

19

Références

Mol Cancer Ther. 2012 Feb;11(2):257-66
pubmed: 22323494
J Biol Chem. 2006 Mar 17;281(11):7437-44
pubmed: 16410248
Front Cell Dev Biol. 2019 Apr 24;7:60
pubmed: 31106200
Appl Radiat Isot. 2020 Feb;156:108867
pubmed: 31883763
ChemMedChem. 2020 Apr 20;15(8):695-704
pubmed: 32057189
Mol Med Rep. 2015 May;11(5):3203-11
pubmed: 25593080
Proteomics Clin Appl. 2014 Jun;8(5-6):454-63
pubmed: 24470260
Front Biosci (Landmark Ed). 2018 Jun 1;23:1933-1968
pubmed: 29772538
J Nucl Med. 2019 Oct;60(10):1421-1429
pubmed: 30850501
Chem Commun (Camb). 2016 Sep 29;52(80):11889-11892
pubmed: 27711378
ChemMedChem. 2015 Jun;10(6):1019-26
pubmed: 25899500
Chem Soc Rev. 2014 Jan 7;43(1):260-90
pubmed: 24173525
ACS Med Chem Lett. 2019 Jul 09;10(8):1173-1179
pubmed: 31413802
EJNMMI Res. 2019 May 23;9(1):48
pubmed: 31123943
Cancer Res. 2002 Aug 15;62(16):4767-72
pubmed: 12183436
Cancer Biol Ther. 2012 Feb 1;13(3):123-9
pubmed: 22236832
Clin Chim Acta. 2019 Aug;495:154-160
pubmed: 30981844
J Nucl Med. 2018 Sep;59(9):1415-1422
pubmed: 29626119
J Nucl Med. 2018 Sep;59(9):1423-1429
pubmed: 29626120
Nat Rev Drug Discov. 2019 Feb;18(2):99-115
pubmed: 30470818
J Med Chem. 2017 Oct 26;60(20):8385-8393
pubmed: 28953383
J Nucl Med. 2020 Apr;61(4):563-569
pubmed: 31586001
J Med Chem. 2008 Oct 9;51(19):6005-13
pubmed: 18783201
Nuklearmedizin. 2020 May 11;:
pubmed: 32392592
J Nucl Med. 2014 Jun;55(6):1023-8
pubmed: 24752674
Chem Soc Rev. 2011 May;40(5):2330-46
pubmed: 21399835
EJNMMI Radiopharm Chem. 2017;1(1):4
pubmed: 29564381
J Med Chem. 2013 May 9;56(9):3467-77
pubmed: 23594271
Oncol Lett. 2017 Sep;14(3):2611-2620
pubmed: 28927027
Virchows Arch. 2015 Oct;467(4):367-82
pubmed: 26259962
J Biol Chem. 1999 Dec 17;274(51):36505-12
pubmed: 10593948
Oncotarget. 2016 May 31;7(22):33472-82
pubmed: 26985769
J Nucl Med. 2019 Mar;60(3):386-392
pubmed: 30072500
J Biol Chem. 2005 May 20;280(20):19441-4
pubmed: 15809306
J Nucl Med. 2019 Jun;60(6):801-805
pubmed: 30954939
Org Biomol Chem. 2011 Apr 7;9(7):2133-41
pubmed: 21290068
Chem Soc Rev. 2013 Nov 7;42(21):8220-36
pubmed: 23873344
Eur J Nucl Med Mol Imaging. 2019 Jul;46(8):1754-1755
pubmed: 31119317
Hepatology. 1999 Jun;29(6):1768-78
pubmed: 10347120
Clin Cancer Res. 2007 Mar 15;13(6):1736-41
pubmed: 17363526
Proc Natl Acad Sci U S A. 1994 Jun 7;91(12):5657-61
pubmed: 7911242
J Med Chem. 2014 Apr 10;57(7):3053-74
pubmed: 24617858

Auteurs

Euy Sung Moon (ES)

Department of Chemistry - TRIGA Site, Johannes Gutenberg University Mainz, 55128, Mainz, Germany.

Filipe Elvas (F)

Department of Nuclear Medicine, Antwerp University Hospital (UZA), 2650, Edegem, Belgium.

Gwendolyn Vliegen (G)

Department of Pharmaceutical Sciences, Laboratory of Medical Biochemistry, University of Antwerp, 2610, Wilrijk, Belgium.

Stef De Lombaerde (S)

Department of Nuclear Medicine, Antwerp University Hospital (UZA), 2650, Edegem, Belgium.

Christel Vangestel (C)

Department of Nuclear Medicine, Antwerp University Hospital (UZA), 2650, Edegem, Belgium.

Sven De Bruycker (S)

Molecular Imaging Center Antwerp (MICA), University of Antwerp, 2610, Wilrijk, Belgium.

An Bracke (A)

Department of Pharmaceutical Sciences, Laboratory of Medical Biochemistry, University of Antwerp, 2610, Wilrijk, Belgium.

Elisabeth Eppard (E)

Positronpharma SA, 7500921 Providencia, Santiago, Chile.

Lukas Greifenstein (L)

Department of Chemistry - TRIGA Site, Johannes Gutenberg University Mainz, 55128, Mainz, Germany.

Benedikt Klasen (B)

Department of Chemistry - TRIGA Site, Johannes Gutenberg University Mainz, 55128, Mainz, Germany.

Vasko Kramer (V)

Positronpharma SA, 7500921 Providencia, Santiago, Chile.

Steven Staelens (S)

Molecular Imaging Center Antwerp (MICA), University of Antwerp, 2610, Wilrijk, Belgium.

Ingrid De Meester (I)

Department of Pharmaceutical Sciences, Laboratory of Medical Biochemistry, University of Antwerp, 2610, Wilrijk, Belgium.

Pieter Van der Veken (P)

Department of Pharmaceutical Sciences, Laboratory of Medical Biochemistry, University of Antwerp, 2610, Wilrijk, Belgium.

Frank Rösch (F)

Department of Chemistry - TRIGA Site, Johannes Gutenberg University Mainz, 55128, Mainz, Germany. frank.roesch@uni-mainz.de.

Classifications MeSH