18 F-trifluoroborate derivatives of [des-Arg 10 ]kallidin for imaging bradykinin B1 receptor expression with positron emission tomography

Molecular Pharmaceutics

Volumn 12, Issue 3, 2015, Pages 974-982

  Liu, Zhibo ^a   Amouroux, Guillaume ^b   Zhang, Zhengxing ^b   Pan, Jinhe ^b   Hundal Jabal, Navjit ^b   Colpo, Nadine ^b   Lau, Joseph ^b   Perrin, David M ^a   Bénard, Franҫois ^a,b   Lin, Kuo Shyan ^a,b  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b BRITISH COLUMBIA CANCER AGENCY   (Canada)

Author keywords

B9858; B9958; bradykinin B1 receptor; fluorine 18; positron emission tomography; trifluoroborate

Indexed keywords

BRADYKININ B1 RECEPTOR; FLUORINE 18; KALLIDIN DERIVATIVE; LYSYLLYSYLARGINYLPROLYL(4 HYDROXYPROLYL)GLYCYL 2 (2,3 DIHYDRO 1H INDEN 2 YL)GLYCYLSERYL 2 (2,3 DIHYDRO 1H INDEN 2 YL)GLYCYLOCTAHYDRO 1H INDOLE 2 CARBOXYLIC ACID; N PROPARGYL N,N DIMETHYLAMMONIOMETHYL TRIFLUOROBORATE F 18; TRACER; UNCLASSIFIED DRUG; BORIC ACID; BRADYKININ; BRADYKININ B1 RECEPTOR ANTAGONIST; FLUORINE; KALLIDIN; RADIOPHARMACEUTICAL AGENT;

AMINO ACID SEQUENCE; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; COMPETITIVE BINDING ASSAY; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG UPTAKE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VITRO STUDY; ISOTOPE LABELING; MALE; MOLECULAR IMAGING; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROTEIN EXPRESSION; RADIOCHEMISTRY; ANALOGS AND DERIVATIVES; ANIMAL; CHEMISTRY; DRUG STABILITY; EXPERIMENTAL NEOPLASM; HEK293 CELL LINE; KNOCKOUT MOUSE; METABOLISM; PHARMACEUTICS; SCINTISCANNING; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; BIOPHARMACEUTICS; BORATES; BRADYKININ; BRADYKININ B1 RECEPTOR ANTAGONISTS; DRUG STABILITY; FLUORINE RADIOISOTOPES; HEK293 CELLS; HUMANS; KALLIDIN; MALE; MICE; MICE, KNOCKOUT; NEOPLASMS, EXPERIMENTAL; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTOR, BRADYKININ B1; TISSUE DISTRIBUTION;

EID: 84924092985     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.5b00003     Document Type: Article

References (33)

1. Campos, M. M.; Leal, P. C.; Yunes, R. A.; Calixto, J. B. Non-peptide antagonists for kinin B1 receptors: new insights into their therapeutic potential for the management of inflammation and pain Trends Pharmacol. Sci. 2006, 27, 646-651
2. Calixto, J. B.; Medeiros, R.; Fernandes, E. S.; Ferreira, J.; Cabrini, D. A.; Campos, M. M. Kinin B1 receptors: key G-protein-coupled receptors and their role in inflammatory and painful processes Br. J. Pharmacol. 2004, 143, 803-818
3. Leeb-Lundberg, L. M. F.; Marceau, F.; Muller-Esterl, W.; Pettibone, D. J.; Zuraw, B. L. International union of pharmacology. XLV. Classification of the kinin receptor family: from molecular mechanisms to pathophysiological consequences Pharmacol. Rev. 2005, 57, 27-77
4. Ni, A.; Chao, L.; Chao, J. Transcription factor nuclear factor κB regulates the inducible expression of the human B1 receptor gene in inflammation J. Biol. Chem. 1998, 273, 2784-2791
5. Molina, L.; Matus, C. E.; Astroza, A.; Pavicic, F.; Tapia, E.; Toledo, C.; Perez, J. A.; Nualart, F.; Gonzalez, C. B.; Burgos, R. A.; Figueroa, C. D.; Ehrenfeld, P.; Poblete, M. T. Stimulation of the bradykinin B1 receptor induces the proliferation of estrogen-sensitive breast cancer cells and activates the ERK1/2 signaling pathway Breast Cancer Res. Treat. 2009, 118, 499-510
6. Taub, J. S.; Guo, R.; Leeb-Lundberg, L. M. F.; Madden, J. F.; Daaka, Y. Bradykinin receptor subtype 1 expression and function in prostate cancer Cancer Res. 2003, 63, 2037-2041
7. Chee, J.; Naran, A.; Misso, N. L.; Thompson, P. J.; Bhoola, K. D. Expression of tissue and plasma kallikreins and kinin B1 and B2 receptors in lung cancer Biol. Chem. 2008, 389, 1225-1233
8. 1 receptors in precursor lesions of gallbladder carcinoma World J. Gastroenterol. 2012, 18, 1208-1215
9. Zelawski, W.; Machnik, G.; Nowaczyk, G.; Plewka, D.; Lorenc, Z.; Sosada, K.; Stadnicki, A. Expression and localisation of kinin receptors in colorectal polyps Int. Immunopharmacol. 2006, 6, 997-1002
10. Fujita, M.; Andoh, T.; Ohashi, K.; Akira, A.; Saiki, I.; Kuraishi, Y. Roles of kinin B1 and B2 receptors in skin cancer pain produced by orthotopic melanoma inoculation in mice Eur. J. Pain 2010, 14, 588-594
11. Moodley, R.; Snyman, C.; Odhav, B.; Bhoola, K. D. Visualisation of transforming growth factor-β1, tissue kallikrein, and kinin and transforming growth factor-β receptors on human clear-cell renal carcinoma cells Biol. Chem. 2005, 386, 375-382
12. Dlamini, Z.; Raidoo, D.; Bhoola, K. Visualisation of tissue kallikrein and kinin receptors in oesophageal carcinoma Immunopharmacology 1999, 43, 303-310
13. Raidoo, D. M.; Sawant, S.; Mahabeer, R.; Bhoola, K. D. Kinin receptors are expressed in human astrocytic tumor cells Immunopharmacology 1999, 43, 255-263
14. da Costa, P. L. N.; Sirois, P.; Tannock, I. F.; Chammas, R. The role of kinin receptors in cancer and therapeutic opportunities Cancer Lett. 2014, 345, 27-38
15. van Kruchten, M.; Hospers, G. A. P.; Glaudemans, A. W. J. M.; Hollema, H.; Arts, H. J. G.; Reyners, A. K. L. Positron emission tomography imaging of oestrogen receptor-expression in endometrial stromal sarcoma supports oestrogen receptor-targeted therapy: case report and review of the literature Eur. J. Cancer 2013, 49, 3850-3855
16. Smith, T. A. D. Towards detecting the HER-2 receptor and metabolic changes induced by HER-2-targeted therapies using medical imaging Br. J. Radiol. 2010, 83, 638-644
17. Jacobs, A. H.; Li, H.; Winkeler, A.; Hilker, R.; Knoess, C.; Ruger, A.; Galldiks, N.; Schaller, B.; Sobesky, J.; Kracht, L.; Monfared, P.; Klein, M.; Vollmar, S.; Bauer, B.; Wagner, R.; Graf, R.; Wienhard, K.; Herholz, K.; Heiss, W. D. PET-based molecular imaging in neuroscience Eur. J. Nucl. Med. Mol. Imaging 2003, 30, 1051-1065
18. Meyer, J. H. Imaging the serotonin transporter during major depressive disorder and antidepressant treatment J. Psychiatry Neurosci. 2007, 32, 86-102
19. Guilloteau, D.; Chalon, S. PET and SPECT exploration of central monoaminergic transporters for the development of new drugs and treatments in brain disorders Curr. Pharm. Des. 2005, 11, 3237-3245
20. Fuchs, K.; Fischer, K.; Schwenck, J.; Kesenheimer, C.; Abbas, S.; Stiller, D.; Hauel, N. H.; Jung, B.; Kneilling, M.; Pichler, B. J. In vivo PET imaging of bradykinin receptor 1 (B1R) expression in a mouse model of chronic inflammation, Proceedings of the 2011 World Molecular Imaging Congress, San Diego, CA, September 7-10, 2011; S865.
21. Lin, K.-S.; Pan, J.; Amouroux, G.; Turashvili, G.; Mesak, F.; Hundal-Jabal, N.; Pourghiasian, M.; Lau, J.; Aparicio, S. J.; Bénard, F. In vivo imaging of bradykinin receptor B1, a widely overexpressed molecule in human cancer Cancer Res. 2014, 75, 387-393
22. Stewart, J. M.; Gera, L.; Chan, D. C.; Whalley, E. T.; Hanson, W. L.; Zuzack, J. S. Potent, long-acting bradykinin antagonists for a wide range of applications Can. J. Physiol. Pharmacol. 1997, 75, 719-724
23. Regoli, D.; Allogho, S. N.; Rizzi, A.; Gobeil, F. Bradykinin receptors and their antagonists Eur. J. Pharmacol. 1998, 348, 1-10
24. Gera, L.; Stewart, J. M.; Fortin, J.-P.; Morissette, G.; Marceau, F. Structural modification of the highly potent peptide bradykinin B1 receptor antagonist B9958 Int. Immunopharmacol. 2008, 8, 289-92
25. + -emitting compounds based on fluorine-18 Top. Curr. Chem. 2002, 222, 201-258
26. 18 F-labeling at high specific activity with correlated in vivo PET Imaging and ex vivo fluorescence Bioconjugate Chem. 2014, 25, 1951-1962
27. 18 F-labelling Angew. Chem., Int. Ed. 2014, 53, 11876-11880
28. 18 F-trifluoroborate octreotate derivative for somatostatin receptor imaging J. Nucl. Med. 2014, 55, 1499-505
29. Levesque, L.; Harvey, N.; Rioux, F.; Drapeau, G.; Marceau, F. Development of a binding assay for the B1 receptors for kinins Immunopharmacology 1995, 29, 141-147
30. Bawolak, M. T.; Gera, L.; Morissette, G.; Bouthillier, J.; Stewart, J. M.; Gobeil, L.-A.; Lodge, R.; Adam, A.; Marceau, F. Fluorescent ligands of the bradykinin B1 receptors: pharmacologic characterization and application to the study of agonist-induced receptor translocation and cell surface receptor expression J. Pharmacol. Exp. Ther. 2009, 329, 159-68
31. 9 -bradykinin J. Neuroinflammation 2009, 6, 11
32. 68 Ga]-labeled bombesin analog BAY86-7548 Clin. Cancer Res. 2013, 19, 5434-5443
33. Vegt, E.; de Jong, M.; Wetzels, J. F. M.; Masereeuw, R.; Melis, M.; Oyen, W. J. G.; Gotthardt, M.; Boerman, O. C. Renal toxicity of radiolabeled peptides and antibody fragments: mechanisms, impact on radionuclide therapy, and strategies for prevention J. Nucl. Med. 2010, 51, 1049-1058