Influence of the molecular charge on the biodistribution of bombesin analogues labeled with the [99mTc(CO)3]-core

Bioconjugate Chemistry

Volumn 19, Issue 12, 2008, Pages 2409-2416

  García Garayoa, Elisa ^a   Schweinsberg, Christian ^a   Maes, Veronique ^b   Brans, Luc ^b   Bläuenstein, Peter ^a   Tourwe, Dirk A ^b   Schibli, R ^a   Schubiger, P August ^a  

^a PAUL SCHERRER INSTITUTE   (Switzerland)

^b VRIJE UNIVERSITEIT BRUSSEL   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BOMBESIN DERIVATIVE; CHELATING AGENT; TECHNETIUM 99M; TRICARBOXYLIC ACID; TRICARBOXYLIC ACID TECHNETIUM 99M; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CELL TRANSPORT; CONTROLLED STUDY; DRUG DISTRIBUTION; FEMALE; HUMAN; HUMAN CELL; HYDROPHILICITY; INTERNALIZATION; KIDNEY TUBULE ABSORPTION; MOUSE; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN BINDING; PROTEIN LOCALIZATION; PROTEIN STRUCTURE; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; SWISS WEBSTER MOUSE; TUMOR CELL;

EID: 58149096143     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800262m     Document Type: Article

References (36)

1. Reubi, J. C. (2003) Peptide receptors as molecular targets for cancer diagnosis and therapy. Endocr. Rev. 24, 389-427.
2. Heppeler, A., Froidevaux, S., Eberle, A. N., and Maecke, H. R. (2000) Receptor targeting for tumor localisation and therapy with radiopeptides. Curr. Med. Chem. 7, 971-994.
3. Krenning, E. P., Kwekkeboom, D. J., Valkema, R., Pauwels, S., Kvols, L. K., and De Jong, M. (2004) Peptide receptor radionuclide therapy. Ann. N.Y. Acad. Sci. 1014, 234-245.
4. Dijkgraaf, I., Boerman, O. C., Oyen, W. J. G., Corstens, F. H. M., and Gotthardt, M. (2007) Development and application of peptide-based radiopharmaceuticals. Anticancer Agents Med. Chem. 7, 543-551.
5. Okarvi, S. M. (2004) Peptide-based radiopharmaceuticals: Future tools for diagnostic imaging of cancers and other diseases. Med. Res. Rev. 24, 357-397.
6. Smith, C. J., Volkert, W. A., and Hoffman, T. J. (2005) Radiolabeled peptide conjugates for targeting of the bombesin receptor superfamily subtypes. Nucl. Med. Biol. 32, 733-740.
7. Reubi, J., Gugger, M., and Waser, B. (2002) Co-expressed peptide receptors in breast cancer as a molecular basis for in vivo multireceptor tumour targeting. Eur. J. Nucl. Med. Mol. Imaging 29, 855-862.
8. Markwalder, R., and Reubi, J. C. (1999) Gastrin-releasing peptide receptors in the human prostate: relation to neoplastic transformation. Cancer Res. 59, 1152-1159.
9. Parry, J., Andrews, R., and Rogers, B. (2007) MicroPET imaging of breast cancer using radiolabeled bombesin analogs targeting the gastrin-releasing peptide receptor. Breast Cancer Res. Treat. 101, 175-183.
10. Zhou, J., Chen, J., Mokotoff, M., Zhong, R., Shultz, L. D., and Ball, E. D. (2003) Bombesin/gastrin-releasing peptide receptor: a potential target for antibody-mediated therapy of small cell lung cancer. Clin. Cancer Res. 9, 4953-4960.
11. 99mTc: a preclinical study. J. Med. Chem. 48, 100-110.
12. 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.
13. 2: an in vitro/in vivo assessment of the targeting ability of this new radiopharmaceutical for PC-3 human prostate cancer cells. Nucl. Med. Biol. 30, 101-109.
14. 2: An in vitro/in vivo structure-activity relationship study where X = 0-, 3-, 5-, 8-, and 11-carbon tethering moieties. Bioconjugate Chem. 14, 93-102.
15. 99Tc. Eur. J. Nucl. Med. 7, 35-36.
16. Garcia-Garayoa, E., Schibli, R., and Schubiger, P. A. (2007) Peptides radiolabeled with Re-186/188 and Tc-99m as potential diagnostic and therapeutic agents. Nucl. Sci. Technol. 18, 88-100.
17. 99mTc-labeled small peptides as diagnostic radiopharmaceuticals. Chem. Rev. 99, 2235-2268.
18. 99mTc(I)-tricarbonyl complexes: a hint for the future functionalization of biomolecules. Bioconjugate Chem. 11, 345-351.
19. 99mTc(I)-postlabeled high affinity bombesin analogue as a potential tumor imaging agent. Bioconjugate Chem. 13, 599-604.
20. 3 bombesin analogues. Nucl. Med. Biol. 34, 17-28.
21. Garcia Garayoa, E., Schweinsberg, C., Maes, V., Ruegg, D., Blanc, A., Blauenstein, P., Tourwe, D. A., Beck-Sickinger, A. G., and Schubiger, P. A. (2007) New [Tc-99m]bombesin analogues with improved biodistribution for targeting gastrin releasing-peptide receptor-positive tumors. Q. J. Nucl. Med. Mol. Imaging 51, 42-50.
22. 64Cu-Labeled DOTA-linker-bombesin(7- 14) analogues containing different amino acid linker moieties. Bioconjugate Chem. 18, 1110-1117.
23. 99mTc(III) '4 + 1' bombesin(7-14) conjugates: synthesis, radiolabeling, and in vitro/in vivo studies. Bioconjugate Chem. 18, 1651-1661.
24. 2] targeting vector for positron-emission tomography imaging of gastrin-releasing peptide receptor-expressing tissues. Proc. Natl. Acad. Sci. U.S.A. 104, 12462-12467.
25. Abele, S., and Seebach, D. (2000) Preparation of achiral and of enantiopure geminally disubstituted beta-amino acids for betapeptide synthesis. Eur. J. Org. Chem. 1-15.
26. Seebach, D., Beck, A. K., and Bierbaum, D. J. (2004) The world of beta- and gamma-peptides comprised of homologated proteinogenic amino acids and other components. Chem. Biodivers. 1, 1111-1239.
27. Smith, C. J., Volkert, W. A., and Hoffman, T. J. (2003) Gastrin releasing peptide (GRP) receptor targeted radiopharmaceuticals: A concise update. Nucl. Med. Biol. 30, 861-868.
28. Schottelius, M., Wester, H. J., Reubi, J. C., Senekowitsch-Schmidtke, R., and Schwaiger, M. (2002) Improvement of pharmacokinetics of radioiodinated Tyr3-octreotide by conjugation with carbohydrates. Bioconjugate Chem. 13, 1021-1030.
29. Alves, S., Correia, J. D. G., Santos, I., Veerendra, B., Sieckman, G. L., Hoffman, T. J., Rold, T. L., Figueroa, S. D., Retzloff, L., McCrate, J., Prasanphanich, A., and Smith, C. J. (2006) Pyrazolyl conjugates of bombesin: a new tridentate ligand framework for the stabilization of fac-[M(CO)(3)](+) moiety. Nucl. Med. Biol. 33, 625-634.
30. Christensen, E. I., Rennke, H. G., and Carone, F. A. (1983) Renal tubular uptake of protein: effect of molecular charge. Am. J. Physiol. Renal Physiol. 244, F436-F441.
31. Decristoforo, C., and Mather, S. J. (2002) The influence of chelator on the pharmacokinetics of Tc-99m-labelled peptides. Q. J. Nucl. Med. Mol. Imaging 46, 195-205.
32. 64Cu-labeled bombesin analogue. Bioconjugate Chem. 14, 756-763.
33. Antunes, P., Ginj, M., Walter, M. A., Chen, J., Reubi, J. C., and Maecke, H. R. (2007) Influence of different spacers on the biological profile of a DOTA-somatostatin analogue. Bioconjugate Chem. 18, 84-92.
34. 111In-DTPA-conjugated peptides. Nucl. Med. Biol. 28, 761-768.
35. 14] bombesin(6-14). Clin. Cancer Res. 8, 1139-1146.
36. 68Ga- labeled bombesin(6-14) analog. J. Nucl. Med. 46, 691-699.