Synthesis of a 68Ga-labeled peptoid?peptide hybrid for imaging of neurotensin receptor expression in vivo

ACS Medicinal Chemistry Letters

Volumn 1, Issue 5, 2010, Pages 224-228

  Maschauer, Simone ^a   Einsiedel, Jürgen ^a   Hocke, Carsten ^a   Hübner, Harald ^a   Kuwert, Torsten ^a   Gmeiner, Peter ^a   Prante, Olaf ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GALLIUM 68; NEUROTENSIN DERIVATIVE; NEUROTENSIN RECEPTOR; PEPTIDE DERIVATIVE; PEPTOID;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG CLEARANCE; DRUG DESIGN; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG TUMOR LEVEL; GENE EXPRESSION; HUMAN; HUMAN CELL; IN VIVO STUDY; INTERNALIZATION; ISOTOPE LABELING; MOUSE; NONHUMAN; NUDE MOUSE; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RELIABILITY; TUMOR CELL;

ANIMALIA; MUS MUSCULUS;

EID: 77956138237     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml1000728     Document Type: Article

References (24)

1. Ametamey, S. M.; Honer, M.; Schubiger, P. A. Molecular imaging with PET Chem. Rev. 2008, 108, 1501-1516
2. Schottelius, M.; Wester, H. J. Molecular imaging targeting peptide receptors Methods 2009, 48, 161-177
3. 13N Radiolabels for Positron Emission Tomography Angew. Chem., Int. Ed. Engl. 2008, 47, 8998-9033
4. Wängler, C.; Schirrmacher, R.; Bartenstein, P.; Wängler, B. Click-Chemistry Reactions in Radiopharmaceutical Chemistry: Fast & Easy Introduction of Radiolabels into Biomolecules for In Vivo Imaging Curr. Med. Chem. 2010, 17, 1092-1116
5. 18F-Radiopharmacy. In Ernst Schering Res Found Workshop; Schubiger, P. A.; Lehmann, L.; Friebe, M., Eds.; Springer: New York, 2007; Vol. 62, pp 215 ? 242.
6. 68Ga for medical application J. Nucl. Med. 2007, 48, 1741-1748
7. Myers, R. M.; Shearman, J. W.; Kitching, M. O.; Ramos-Montoya, A.; Neal, D. E.; Ley, S. V. Cancer, chemistry, and the cell: Molecules that interact with the neurotensin receptors ACS Chem. Biol. 2009, 4, 503-525
8. 99mTc-NT-XI, evaluated in ductal pancreatic adenocarcinoma patients J. Nucl. Med. 2003, 44, 1649-1654
9. 111In-labelled DTPA- and DOTA-conjugated neurotensin analogues for imaging and therapy of exocrine pancreatic cancer Eur. J. Nucl. Med. Mol. Imaging 2003, 30, 1134-1139
10. Garcia-Garayoa, E.; Maes, V.; Blauenstein, P.; Blanc, A.; Hohn, A.; Tourwé, D.; Schubiger, P. A. Double-stabilized neurotensin analogues as potential radiopharmaceuticals for NTR-positive tumors Nucl. Med. Biol. 2006, 33, 495-503
11. 99mTc J. Med. Chem. 2006, 49, 4767-4776
12. 99mTc-labeled neurotensin peptide 8?13 Nucl. Med. Biol. 2006, 33, 505-512
13. 99mTc]Demotensin 5 and 6 in the NTS1-R-targeted imaging of tumours: Synthesis and preclinical results Eur. J. Nucl. Med. Mol. Imaging 2007, 34, 1804-1814
14. Alshoukr, F.; Rosant, C.; Maes, V.; Abdelhak, J.; Raguin, O.; Burg, S.; Sarda, L.; Barbet, J.; Tourwé, D.; Pelaprat, D.; Gruaz-Guyon, A. Novel Neurotensin Analogues for Radioisotope Targeting to Neurotensin Receptor-Positive Tumors Bioconjugate Chem. 2009, 20, 1602-1610
15. Garcia-Garayoa, E.; Blauenstein, P.; Blanc, A.; Maes, V.; Tourwé, D.; Schubiger, P. A. A stable neurotensin-based radiopharmaceutical for targeted imaging and therapy of neurotensin receptor-positive tumours Eur. J. Nucl. Med. Mol. Imaging 2009, 36, 37-47
16. Gambhir, S. S. Molecular imaging of cancer with positron emission tomography Nat. Rev. Cancer 2002, 2, 683-693
17. Einsiedel, J.; Hübner, H.; Hervet, M.; Härterich, S.; Koschatzky, S.; Gmeiner, P. Peptide backbone modifications on the C-terminal hexapeptide of neurotensin Bioorg. Med. Chem. Lett. 2008, 18, 2013-2018
18. Härterich, S.; Koschatzky, S.; Einsiedel, J.; Gmeiner, P. Novel insights into GPCR?peptide interactions: Mutations in extracellular loop 1, ligand backbone methylations and molecular modeling of neurotensin receptor 1 Bioorg. Med. Chem. 2008, 16, 9359-9368
19. 18F- Glycopeptides as Effective Imaging Probes for Positron Emission Tomography Angew. Chem., Int. Ed. Engl. 2010, 49, 976-979
20. Maschauer, S.; Prante, O. A series of 2-O-trifluoromethylsulfonyl-D- mannopyranosides as precursors for concomitant F-18-labeling and glycosylation by click chemistry Carbohydr. Res. 2009, 344, 753-761
21. Trivedi, H. S.; Anson, M.; Steel, P. G.; Worley, J. A method for selective N-Boc deprotection on Wang resin Synlett 2001, 1932-1934
22. Amar, S.; Kitabgi, P.; Vincent, J. P. Activation of phosphatidylinositol turnover by neurotensin receptors in the human colonic adenocarcinoma cell line HT29 FEBS Lett. 1986, 201, 31-36
23. 18F-labeled GnRH-I analogues with high GnRHR-targeting efficiency Bioconjugate Chem. 2008, 19, 1256-1268
24. Heppeler, A.; Froidevaux, S.; Mäcke, H. R.; Jermann, E.; Béhé, M.; Powell, P.; Hennig, M. Radiometal-Labelled Macrocyclic Chelator-Derivatised Somatostatin Analogue with Superb Tumour-Targeting Properties and Potential for Receptor-Mediated Internal Radiotherapy Chemistry 1999, 5, 1974-1981