Design, evaluation, and comparison of ghrelin receptor agonists and inverse agonists as suitable radiotracers for PET imaging

Bioconjugate Chemistry

Volumn 23, Issue 4, 2012, Pages 771-784

  Chollet, Constance ^a   Bergmann, Ralf ^b   Pietzsch, Jens ^b   Beck Sickinger, Annette G ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; BLOOD; METABOLISM; PARAMETER ESTIMATION; PHARMACOKINETICS; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVE TRACERS; TISSUE;

DESIGN EVALUATION; GHRELIN; GHRELIN RECEPTOR; IN-VIVO; INVERSE AGONISTS; PHARMACOKINETIC PROFILES; RECEPTOR LIGANDS; SOLID SUPPORTS; SYNTHESISED; TOMOGRAPHY IMAGING;

PEPTIDES;

1,4,7 TRIAZACYCLONONANE,1 GLUTARIC ACID 4,7 ACETIC ACID GA 68; CHELATING AGENT; GALLIUM 68; GHRELIN RECEPTOR; INOSITOL PHOSPHATE; OCTANOIC ACID; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOLOGICAL ACTIVITY; COMPLEX FORMATION; CONCENTRATION RESPONSE; CONJUGATION; CONTROLLED STUDY; DIFFUSION; DRUG ACCUMULATION; DRUG DESIGN; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG SCREENING; DRUG STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY METABOLISM; LIVER METABOLISM; MALE; MOLECULAR WEIGHT; NONHUMAN; OBESITY; PEPTIDE SYNTHESIS; PLASMA CLEARANCE; POSITRON EMISSION TOMOGRAPHY; PROTEIN METABOLISM; PROTEIN MODIFICATION; RADIOACTIVITY; RADIOCHEMISTRY; RAT; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION;

EID: 84860004816     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc2005889     Document Type: Article

References (27)

1. Nakazato, M., Murakami, N., Date, Y., Kojima, M., Matsuo, H., Kangawa, K., and Matsukura, S. (2001) A role for ghrelin in the central regulation of feeding. Nature 409 (6817), 194-8. (Pubitemid 32144284)
2. Cummings, D. E. (2006) Ghrelin and the short- and long-term regulation of appetite and body weight. Physiol. Behav. 89 (1), 71-84.
3. Howard, A. D., Feighner, S. D., Cully, D. F., Arena, J. P., Liberator, P. A., Rosenblum, C. I., Hamelin, M., Hreniuk, D. L., Palyha, O. C., Anderson, J., Paress, P. S., Diaz, C., Chou, M., Liu, K. K., McKee, K. K., Pong, S. S., Chaung, L. Y., Elbrecht, A., Dashkevicz, M., Heavens, R., Rigby, M., Sirinathsinghji, D. J., Dean, D. C., Melillo, D. G., Patchett, A. A., Nargund, R., Griffin, P. R., DeMartino, J. A., Gupta, S. K., Schaeffer, J. M., Smith, R. G., and Van der Ploeg, L. H. (1996) A receptor in pituitary and hypothalamus that functions in growth hormone release. Science 273 (5277), 974-7. (Pubitemid 26275178)
4. Kojima, M., Hosoda, H., Date, Y., Nakazato, M., Matsuo, H., and Kangawa, K. (1999) Ghrelin is a growth-hormone-releasing acylated peptide from stomach. Nature 402 (6762), 656-60. (Pubitemid 129516334)
5. Ferrini, F., Salio, C., Lossi, L., and Merighi, A. (2009) Ghrelin in central neurons. Curr. Neuropharmacol. 7 (1), 37-49.
6. Kojima, M., and Kangawa, K. (2005) Ghrelin: structure and function. Physiol. Rev. 85 (2), 495-522. (Pubitemid 40404635)
7. Gutierrez, J. A., Solenberg, P. J., Perkins, D. R., Willency, J. A., Knierman, M. D., Jin, Z., Witcher, D. R., Luo, S., Onyia, J. E., and Hale, J. E. (2008) Ghrelin octanoylation mediated by an orphan lipid transferase. Proc. Natl. Acad. Sci. U. S. A. 105 (17), 6320-5. (Pubitemid 351758344)
8. Yang, J., Brown, M. S., Liang, G., Grishin, N. V., and Goldstein, J. L. (2008) Identification of the acyltransferase that octanoylates ghrelin, an appetite-stimulating peptide hormone. Cell 132 (3), 387-96. (Pubitemid 351192001)
9. Cummings, D. E., Weigle, D. S., Frayo, R. S., Breen, P. A., Ma, M. K., Dellinger, E. P., and Purnell, J. Q. (2002) Plasma ghrelin levels after diet-induced weight loss or gastric bypass surgery. N. Engl. J. Med. 346 (21), 1623-30. (Pubitemid 34755670)
10. Holst, B., and Schwartz, T. W. (2006) Ghrelin receptor mutations--too little height and too much hunger. J. Clin. Invest. 116 (3), 637-41. (Pubitemid 43326872)
11. Leite-Moreira, A. F., and Soares, J. B. (2007) Physiological, pathological and potential therapeutic roles of ghrelin. Drug Discovery Today 12 (7-8), 276-88. (Pubitemid 46467484)
12. Chollet, C., Meyer, K., and Beck-Sickinger, A. G. (2009) Ghrelin--a novel generation of anti-obesity drug: design, pharmacomodulation and biological activity of ghrelin analogues. J. Pept. Sci. 15 (11), 711-30.
13. Depoortere, I. (2009) Targeting the ghrelin receptor to regulate food intake. Regul. Pept. 156 (1-3), 13-23.
14. Els, S., Beck-Sickinger, A. G., and Chollet, C. (2010) Ghrelin receptor: high constitutive activity and methods for developing inverse agonists. Methods Enzymol. 485, 103-21.
15. Eisenwiener, K. P., Prata, M. I., Buschmann, I., Zhang, H. W., Santos, A. C., Wenger, S., Reubi, J. C., and Macke, H. R. (2002) NODAGATOC, a new chelator-coupled somatostatin analogue labeled with [67/68Ga] and [111In] for SPECT, PET, and targeted therapeutic applications of somatostatin receptor (hsst2) expressing tumors. Bioconjugate Chem. 13 (3), 530-41. (Pubitemid 34535940)
16. Velikyan, I., Maecke, H., and Langstrom, B. (2008) Convenient preparation of 68Ga-based PET-radiopharmaceuticals at room temperature. Bioconjugate Chem. 19 (2), 569-73. (Pubitemid 351294931)
17. de Sa, A., Matias, A. A., Prata, M. I., Geraldes, C. F., Ferreira, P. M., and Andre, J. P. (2010) Gallium labeled NOTA-based conjugates for peptide receptor-mediated medical imaging. Bioorg. Med. Chem. Lett. 20 (24), 7345-8.
18. Knetsch, P. A., Petrik, M., Griessinger, C. M., Rangger, C., Fani, M., Kesenheimer, C., von Guggenberg, E., Pichler, B. J., Virgolini, I., Decristoforo, C., and Haubner, R. (2011) [(68)Ga]NODAGA-RGD for imaging alpha(v)beta (3) integrin expression. Eur. J. Nucl. Med. Mol. Imaging 38 (7), 1303-12.
19. Bednarek, M. A., Feighner, S. D., Pong, S. S., McKee, K. K., Hreniuk, D. L., Silva, M. V., Warren, V. A., Howard, A. D., Van Der Ploeg, L. H., and Heck, J. V. (2000) Structure-function studies on the new growth hormone-releasing peptide, ghrelin: minimal sequence of ghrelin necessary for activation of growth hormone secretagogue receptor 1a. J. Med. Chem. 43 (23), 4370-6. (Pubitemid 32046862)
20. Holst, B., Lang, M., Brandt, E., Bach, A., Howard, A., Frimurer, T. M., Beck-Sickinger, A., and Schwartz, T. W. (2006) Ghrelin receptor inverse agonists: identification of an active peptide core and its interaction epitopes on the receptor. Mol. Pharmacol. 70 (3), 936-46. (Pubitemid 44268450)
21. Morozumi, N., Hanada, T., Habara, H., Yamaki, A., Furuya, M., Nakatsuka, T., Inomata, N., Minamitake, Y., Ohsuye, K., and Kangawa, K. (2011) The role of C-terminal part of ghrelin in pharmacokinetic profile and biological activity in rats. Peptides 32 (5), 1001-7.
22. De Vriese, C., Hacquebard, M., Gregoire, F., Carpentier, Y., and Delporte, C. (2007) Ghrelin interacts with human plasma lipoproteins. Endocrinology 148 (5), 2355-62. (Pubitemid 46997038)
23. Tornesello, A. L., Aurilio, M., Accardo, A., Tarallo, L., Barbieri, A., Arra, C., Tesauro, D., Morelli, G., and Aloj, L. (2011) Gastrin and cholecystokinin peptide-based radiopharmaceuticals: an in vivo and in vitro comparison. J. Pept. Sci. 17 (5), 405-12.
24. Fani, M., Del Pozzo, L., Abiraj, K., Mansi, R., Tamma, M. L., Cescato, R., Waser, B., Weber, W. A., Reubi, J. C., and Maecke, H. R. (2011) PET of Somatostatin Receptor-Positive Tumors Using 64Cu-and68Ga-Somatostatin Antagonists: The Chelate Makes the Difference. J. Nucl. Med. 52 (7), 1110-8.
25. Gnanapavan, S., Kola, B., Bustin, S. A., Morris, D. G., McGee, P., Fairclough, P., Bhattacharya, S., Carpenter, R., Grossman, A. B., and Korbonits, M. (2002) The tissue distribution of the mRNA of ghrelin and subtypes of its receptor, GHS-R, in humans. J. Clin. Endocrinol. Metab. No. 6, 2988.
26. Zigman, J. M., Jones, J. E., Lee, C. E., Saper, C. B., and Elmquist, J. K. (2006) Expression of ghrelin receptor mRNA in the rat and the mouse brain. J. Comp. Neurol. 494 (3), 528-48. (Pubitemid 41791000)
27. Potter, R., Horti, A. G., Ravert, H. T., Holt, D. P., Finley, P., Scheffel, U., Dannals, R. F., and Wahl, R. L. (2011) Synthesis and in vivo evaluation of (S)-6-(4-fluorophenoxy)-3-((1-[11C]methylpiperidin-3-yl)- methyl)-2-o-tolylquinazolin-4(3H)-one, a potential PET tracer for growth hormone secretagogue receptor (GHSR). Bioorg. Med. Chem. 19 (7), 2368-72.