Stereochemistry of Amino Acid Spacers Determines the Pharmacokinetics of 111In-DOTA-Minigastrin Analogues for Targeting the CCK2/Gastrin Receptor

Bioconjugate Chemistry

Volumn 26, Issue 6, 2015, Pages 1113-1119

  Kolenc Peitl, Petra ^a   Tamma, Marialuisa ^b   Kroselj, Marko ^a   Braun, Friederike ^c   Waser, Beatrice ^d   Reubi, Jean Claude ^d   Sollner Dolenc, Marija ^e   Maecke, Helmut R ^b,c   Mansi, Rosalba ^b,c  

^a UNIVERSITY MEDICAL CENTRE LJUBLJANA   (Slovenia)

^b UNIVERSITY HOSPITAL BASEL   (Switzerland)

^c UNIVERSITY OF FREIBURG   (Germany)

^d UNIVERSITY OF BERN   (Switzerland)

^e UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

DICHROISM; PHARMACOKINETICS; STEREOSELECTIVITY; TUMORS;

AMINO-ACIDS; CIRCULAR DICHROISM MEASUREMENTS; CO-INJECTION; ENZYMATIC STABILITY; GLUTAMIC ACID; N-TERMINALS; PEPTIDE RECEPTOR; POLYGLUTAMIC ACIDS; RADIONUCLIDE THERAPY; SECONDARY STRUCTURES;

AMINO ACIDS;

AMINO ACID; CHOLECYSTOKININ B RECEPTOR; DOTA IN 111; GELATIN SUCCINATE; GLUTAMIC ACID; MINIGASTRIN ANALOG; PEPTIDE DERIVATIVE; POLYGLUTAMIC ACID; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG; 1,4,7,10-TETRAAZACYCLODODECANE- 1,4,7,10-TETRAACETIC ACID; GASTRIN; INDIUM; MINIGASTRIN; SINGLE HETEROCYCLIC RINGS;

AMINO TERMINAL SEQUENCE; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CALCIUM MOBILIZATION ASSAY; CIRCULAR DICHROISM; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG TARGETING; DRUG TUMOR LEVEL; ENZYME STABILITY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; INTERNALIZATION; MALE; MEASUREMENT; MOUSE; NONHUMAN; PROTEIN SECONDARY STRUCTURE; RAT; STEREOCHEMISTRY; AMINO ACID SEQUENCE; ANIMAL; CHEMISTRY; LEWIS RAT; METABOLISM; NEOPLASMS; PHYSIOLOGY; POSITRON EMISSION TOMOGRAPHY; SCINTISCANNING;

AMINO ACID SEQUENCE; ANIMALS; GASTRINS; HETEROCYCLIC COMPOUNDS, 1-RING; HUMANS; INDIUM RADIOISOTOPES; MALE; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; RATS, INBRED LEW; RECEPTOR, CHOLECYSTOKININ B;

EID: 84934979044     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.5b00187     Document Type: Article

References (34)

1. Reubi, J. C., Schaer, J. C., and Waser, B. (1997) Cholecystokinin(CCK)-A and CCK-B/gastrin receptors in human tumors Cancer Res. 57, 1377-1386
2. Reubi, J. C. and Waser, B. (1996) Unexpected high incidence of cholecystokinin-B/gastrin receptors in human medullary thyroid carcinomas Int. J. Cancer 67, 644-647
3. Gotthardt, M., Behe, M. P., Beuter, D., Battmann, A., Bauhofer, A., Schurrat, T., Schipper, M., Pollum, H., Oyen, W. J., and Behr, T. M. (2006) Improved tumour detection by gastrin receptor scintigraphy in patients with metastasised medullary thyroid carcinoma Eur. J. Nucl. Med. Mol. Imaging 33, 1273-1279
4. Gotthardt, M., Behe, M. P., Grass, J., Bauhofer, A., Rinke, A., Schipper, M. L., Kalinowski, M., Arnold, R., Oyen, W. J., and Behr, T. M. (2006) Added value of gastrin receptor scintigraphy in comparison to somatostatin receptor scintigraphy in patients with carcinoids and other neuroendocrine tumours Endocr.-Relat. Cancer 13, 1203-1211
5. 2 receptor splice variant with intron 4 retention in human gastrointestinal and lung tumours J. Cell. Mol. Med. 14, 933-943
6. 111In-labelled minigastrin Eur. J. Nucl. Med. Mol. Imaging 35, 386-392
7. Froberg, A. C., de Jong, M., Nock, B. A., Breeman, W. A., Erion, J. L., Maina, T., Verdijsseldonck, M., de Herder, W. W., van der Lugt, A., Kooij, P. P., and Krenning, E. P. (2009) Comparison of three radiolabelled peptide analogues for CCK-2 receptor scintigraphy in medullary thyroid carcinoma Eur. J. Nucl. Med. Mol. Imaging 36, 1265-1272
8. Laverman, P., Behe, M., Oyen, W. J., Willems, P. H., Corstens, F. H., Behr, T. M., and Boerman, O. C. (2004) Two technetium-99m-labeled cholecystokinin-8 (CCK8) peptides for scintigraphic imaging of CCK receptors Bioconjugate Chem. 15, 561-568
9. Mather, S. J., McKenzie, A. J., Sosabowski, J. K., Morris, T. M., Ellison, D., and Watson, S. A. (2007) Selection of radiolabeled gastrin analogs for peptide receptor-targeted radionuclide therapy J. Nucl. Med. 48, 615-622
10. 99mTc-labeled minigastrin analogs J. Nucl. Med. 46, 1727-1736
11. Reubi, J. C., Waser, B., Schaer, J. C., Laederach, U., Erion, J., Srinivasan, A., Schmidt, M. A., and Bugaj, J. E. (1998) Unsulfated DTPA- and DOTA-CCK analogs as specific high-affinity ligands for CCK-B receptor-expressing human and rat tissues in vitro and in vivo Eur. J. Nucl. Med. 25, 481-490
12. 99mTc-labeling and in vitro and in vivo evaluation of HYNIC- and (Nalpha-His)acetic acid-modified [ d -Glu1]-minigastrin Bioconjugate Chem. 15, 864-871
13. 99mTc-labelled HYNIC-minigastrin with reduced kidney uptake for targeting of CCK-2 receptor-positive tumours Eur. J. Nucl. Med. Mol. Imaging 34, 1209-1218
14. Behe, M. and Behr, T. M. (2002) Cholecystokinin-B (CCK-B)/gastrin receptor targeting peptides for staging and therapy of medullary thyroid cancer and other CCK-B receptor expressing malignancies Biopolymers 66, 399-418
15. Good, S., Walter, M. A., Waser, B., Wang, X., Muller-Brand, J., Behe, M. P., Reubi, J. C., and Maecke, H. R. (2008) Macrocyclic chelator-coupled gastrin-based radiopharmaceuticals for targeting of gastrin receptor-expressing tumours Eur. J. Nucl. Med. Mol. Imaging 35, 1868-1877
16. Breeman, W. A., Froberg, A. C., de Blois, E., van Gameren, A., Melis, M., de Jong, M., Maina, T., Nock, B. A., Erion, J. L., Macke, H. R., and Krenning, E. P. (2008) Optimised labeling, preclinical and initial clinical aspects of CCK-2 receptor-targeting with 3 radiolabeled peptides Nucl. Med. Biol. 35, 839-849
17. Gotthardt, M., van Eerd-Vismale, J., Oyen, W. J., de Jong, M., Zhang, H., Rolleman, E., Maecke, H. R., Behe, M., and Boerman, O. (2007) Indication for different mechanisms of kidney uptake of radiolabeled peptides J. Nucl. Med. 48, 596-601
18. Vegt, E., van Eerd, J. E., Eek, A., Oyen, W. J., Wetzels, J. F., de Jong, M., Russel, F. G., Masereeuw, R., Gotthardt, M., and Boerman, O. C. (2008) Reducing renal uptake of radiolabeled peptides using albumin fragments J. Nucl. Med. 49, 1506-1511
19. Kolenc-Peitl, P., Mansi, R., Tamma, M., Gmeiner-Stopar, T., Sollner-Dolenc, M., Waser, B., Baum, R. P., Reubi, J. C., and Maecke, H. R. (2011) Highly improved metabolic stability and pharmacokinetics of indium-111-DOTA-gastrin conjugates for targeting of the gastrin receptor J. Med. Chem. 54, 2602-2609
20. Dubreuil, P., Fulcrand, P., Rodriguez, M., Fulcrand, H., Laur, J., and Martinez, J. (1989) Novel activity of angiotensin-converting enzyme. Hydrolysis of cholecystokinin and gastrin analogues with release of the amidated C-terminal dipeptide Biochem. J. 262, 125-130
21. Dubreuil, P., Fulcrand, P., Rodriguez, M., Laur, J., Bali, J. P., and Martinez, J. (1990) ACE-like hydrolysis of gastrin analogs and CCK-8 by fundic mucosal cells of different species with release of the amidated C-terminal dipeptide Biochim. Biophys. Acta 1039, 171-176
22. Roques, B. P., Noble, F., Dauge, V., Fournie-Zaluski, M. C., and Beaumont, A. (1993) Neutral endopeptidase 24.11: structure, inhibition, and experimental and clinical pharmacology Pharmacol. Rev. 45, 87-146
23. Reed, J. and Reed, T. A. (1997) A set of constructed type spectra for the practical estimation of peptide secondary structure from circular dichroism Anal. Biochem. 254, 36-40
24. Behr, T. M., Sharkey, R. M., Sgouros, G., Blumenthal, R. D., Dunn, R. M., Kolbert, K., Griffiths, G. L., Siegel, J. A., Becker, W. S., and Goldenberg, D. M. (1997) Overcoming the nephrotoxicity of radiometal-labeled immunoconjugates: improved cancer therapy administered to a nude mouse model in relation to the internal radiation dosimetry Cancer 80, 2591-2610
25. 111In-octreotide in mice and rats J. Nucl. Med. 47, 528-533
26. ten Dam, M. A., Branten, A. J., Klasen, I. S., and Wetzels, J. F. (2001) The gelatin-derived plasma substitute gelofusine causes low-molecular-weight proteinuria by decreasing tubular protein reabsorption J. Crit. Care 16, 115-120
27. Vegt, E., Melis, M., Eek, A., de Visser, M., Brom, M., Oyen, W. J., Gotthardt, M., de Jong, M., and Boerman, O. C. (2011) Renal uptake of different radiolabelled peptides is mediated by megalin: SPECT and biodistribution studies in megalin-deficient mice Eur. J. Nucl. Med. Mol. Imaging 38, 623-632
28. 111In-labelled gastrin/CCK2 receptor-targeting peptides Eur. J. Nucl. Med. Mol. Imaging 38, 1410-1416
29. 111In-DTPAGlu-G-CCK8 for cholecystokinin-B receptor imaging J. Nucl. Med. 45, 485-494
30. Fani, M., Mueller, A., Tamma, M. L., Nicolas, G., Rink, H. R., Cescato, R., Reubi, J. C., and Maecke, H. R. (2010) Radiolabeled bicyclic somatostatin-based analogs: a novel class of potential radiotracers for SPECT/PET of neuroendocrine tumors J. Nucl. Med. 51, 1771-1779
31. Erchegyi, J., Cescato, R., Grace, C. R., Waser, B., Piccand, V., Hoyer, D., Riek, R., Rivier, J. E., and Reubi, J. C. (2009) Novel, potent, and radio-iodinatable somatostatin receptor 1 (sst1) selective analogues J. Med. Chem. 52, 2733-2746
32. Reubi, J. C., Kvols, L. K., Waser, B., Nagorney, D. M., Heitz, P. U., Charboneau, J. W., Reading, C. C., and Moertel, C. (1990) Detection of somatostatin receptors in surgical and percutaneous needle biopsy samples of carcinoids and islet cell carcinomas Cancer Res. 50, 5969-5977
33. Zhang, H., Chen, J., Waldherr, C., Hinni, K., Waser, B., Reubi, J. C., and Maecke, H. R. (2004) Synthesis and evaluation of bombesin derivatives on the basis of pan-bombesin peptides labeled with indium-111, lutetium-177, and yttrium-90 for targeting bombesin receptor-expressing tumors Cancer Res. 64, 6707-6715
34. Cescato, R., Maina, T., Nock, B., Nikolopoulou, A., Charalambidis, D., Piccand, V., and Reubi, J. C. (2008) Bombesin receptor antagonists may be preferable to agonists for tumor targeting J. Nucl. Med. 49, 318-326