Spacer site modifications for the improvement of the in vitro and in vivo binding properties of99mTc-N3S-X-bombesin[2-14] derivatives

Bioconjugate Chemistry

Volumn 20, Issue 5, 2009, Pages 856-867

  Fragogeorgi, Eirini A ^a   Zikos, Christos ^a,b   Gourni, Eleni ^a   Bouziotis, Penelope ^a   Paravatou Petsotas, Maria ^a   Loudos, George ^c   Mitsokapas, Nikolaos ^a   Xanthopoulos, Stavros ^a   Mavri Vavayanni, Mary ^d   Livaniou, Evangelia ^a   Varvarigou, Alexandra D ^a   Archimandritis, Spyridon C ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

^b Biomedica Life Sciences SA   (Greece)

^c UNIVERSITY OF WEST ATTICA   (Greece)

^d Ethnikon Kai Kapodistriakon Panepistimion Athinon   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BINDING ENERGY; CELL CULTURE; CELLS; DISEASES; MAMMALS; PLASMA STABILITY; RADIOISOTOPES; SINGLE PHOTON EMISSION COMPUTED TOMOGRAPHY; TUMORS;

BINDING PROPERTIES; BIODISTRIBUTIONS; CANCER CELLS; HIGH AFFINITY; IN-VITRO; IN-VIVO; PEPTIDE RECEPTOR; RE COMPLEX; VITRO AND IN VIVO; VIVO EVALUATION;

PEPTIDES;

BOMBESIN DERIVATIVE; BOMBESIN PLUS RHENIUM TECHNETIUM TC 99M CONJUGATE; CYSTEINE; GASTRIN RELEASING PEPTIDE RECEPTOR; GLYCINE; GLYCYLGLYCYLCYSTEININE PLUS BOMBESIN; ORNITHINE; ORNITHYLORNITHYLORNITHINE PLUS BOMBESIN; TECHNETIUM 99M; UNCLASSIFIED DRUG; BOMBESIN; GLUCONIC ACID; ISOTOPE; RHENIUM; TECHNETIUM COMPLEX;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CELL STRAIN; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; INTERNALIZATION; ISOTOPE LABELING; KIDNEY HOMOGENATE; LIVER HOMOGENATE; MASS SPECTROMETRY; MOUSE; NONHUMAN; PROSTATE CANCER; RADIOCHEMISTRY; SCID MOUSE; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; SWISS WEBSTER MOUSE; ANIMAL; CHEMISTRY; KIDNEY; LIQUID CHROMATOGRAPHY; LIVER; MALE; METABOLISM; SYNTHESIS; TRANSPORT AT THE CELLULAR LEVEL; TUMOR CELL LINE;

ANIMALIA; MAMMALIA; MUS;

ANIMALS; BIOLOGICAL TRANSPORT; BOMBESIN; CELL LINE, TUMOR; CHROMATOGRAPHY, LIQUID; FEMALE; GLUCONATES; HUMANS; ISOTOPES; KIDNEY; LIVER; MALE; MICE; ORGANOTECHNETIUM COMPOUNDS; RADIOCHEMISTRY; RHENIUM; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 66249146075     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800475k     Document Type: Article

References (56)

1. Anastasi, A., Erspamer, V., and Nucci, M. (1972) Isolation and aminoacid sequences of alytensin and bombesin, two analogous active tetradecapeptides from the skin of european discoglossid frogs. Arch. Biochem. Biophys. 148, 443-446.
2. Nagalla, S. R., Barry, B. J., Falicks, A. M., Gibson, B. W., Taylor, J. E., Dong, J. Z., and Spindel, E. R. (1996) There are three distinct forms of bombesin. J. Biol. Chem. 271, 7731-7737.
3. Ohki-Hamazaki, H., Iwabuchi, M., and Maekawa, F. (2005) Development and function of bombesin-like peptides and their receptors. Int. J. Dev. Biol. 49, 293-300. (Pubitemid 40917351)
4. Cornelio, D. B., Roesler, R., and Schwartsmann, G. (2007) Gastrin-releasing peptide receptor as a molecule target in experimental anticancer therapy. Ann. Oncol. 18, 1457-1466. (Pubitemid 47365477)
5. Dietrich, J. B. (1994) Neuropeptides, antagonists and cell proliferation: bombesin as an example. Cell. Mol. Biol. 40, 731-746.
6. Patel, O., Shulkes, A., and Baldwin, G. S. (2006) Gastrin-releasing peptide and cancer. Biochim. Biophys. Acta 1766, 23-41. (Pubitemid 44175629)
7. Qu, X., Xiao, D., and Weber, C. H. (2003) Biologic relevance of mammalian bombesin-like peptides and their receptors in human malignancies. Curr. Opin. Endocrinol. Diabetes Obes. 10, 60-71. (Pubitemid 41623173)
8. Giblin, M. F., Veerendra, B., and Smith, C. J. (2005) Radiometallation of receptor-specific peptides for diagnosis and treatment of human cancer. In Vivo 19, 9-29. (Pubitemid 40450375)
9. 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. (Pubitemid 41502979)
10. 3 bombesin analogues. Nucl. Med. Biol. 34, 17-28.
11. 99mTc]bombesin analogues with improved biodistribution for targeting gastrin releasing-peptide receptor-positive tumors. Q. J. Nucl. Med. Mol. Imaging 51, 42-50.
12. La Bella, R., Garcia-Garayoa, E., Bahler, M., Blauenstein, P., Schibli, R., Conrath, P., Tourwe, D., and Schubiger, P. A. (2002) A 99mTc(I)-postlabeled high affinity bombesin analogue as a potential tumor imaging agent. Bioconjugate Chem. 13, 599-604. (Pubitemid 34527522)
13. 2: An in vitro/in vivo structure-sctivity relationship study where X=0-, 3-, 5-, 8-, and 11-carbon tethering moieties. Bioconjugate Chem. 14, 93-102.
14. 3. Cancer Res. 63, 4082-4088.
15. 2 (X=serylserylserine, glycylglycylglycine, glycylserylglycine, or beta alanine). Synth. React. Inorg., Met.-Org., Nano-Met. Chem. 36, 481-491.
16. 3]+ moiety. Nucl. Med. Biol. 33, 625-634.
17. 99mTc(III) '4 + 1' bombesin(7-14) conjugates: synthesis, radiolabeling, and in vitro/in vivo studies. Bioconjugate Chem. 18, 1651-1661.
18. Parry, J. J., Andrews, R., and Rogers, B. E. (2006) Micropet imaging of breast cancer using radiolabeled bombesin analogs targeting the gastrin-releasing peptide receptor. Breast Cancer Res. Treat. 101, 175-184.
19. 64Cu-labeled DOTA-linker-bombesin(7- 14) analogues containing different amino acid linker moieties. Bioconjugate Chem. 18, 1110-1117.
20. 64Cu-labeled polyethylene glycol-bombesin conjugate. Cancer Biother. Radiopharm. 19, 25-34.
21. 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.
22. 68Ga- labeled bombesin (6-14) analog. J. Nucl. Med. 46, 691-699.
23. Zhang, X., Cai, W., Cao, F., Schreibmann, E., Wu, Y., Wu, J. C., Xing, L., and Chen, X. (2006) 18F-Labeled bombesin analogs for targeting GRP receptor-expressing prostate cancer. J. Nucl. Med. 47, 492-501. (Pubitemid 46768492)
24. 111In-labeled bombesin analogs as potential radiopharmaceuticals for specific targeting of gastrin-releasing peptide receptors expressed on human prostate cancer cells. J. Nucl. Med. 44, 823-831.
25. 2 structural paradigm in a prostate cancer model. Bioconjugate Chem. 19, 1803-1812.
26. 2. Nucl. Med. Biol. 29, 423-430.
27. 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, lutecium-177, and yttrium-90 for targeting bombesin receptor-expressing tumors. Cancer Res. 64, 6707-6715. (Pubitemid 39302601)
28. 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. (Pubitemid 46145997)
29. Zhang, H., Schuhmacher, J., Waser, B., Wild, D., Eisenhut, M., Reubi, J. C., and Maecke, H. R. (2007) DOTA-PESIN, a DOTA-conjugated bombesin derivative designed for the imaging and targeted radionuclide treatment of bombesin receptor-positive tumors. Eur. J. Nucl. Med. Mol. Imaging 34, 1198-1208. (Pubitemid 47296770)
30. 2]: syntheses, radiolabeling and in vitro/in vivo GRP receptor targeting studies. Anticancer Res. 23, 63-70.
31. 2NS peptidic chelator: evidence of interconversion between the syn and anti conformations. Inorg. Chem. 36, 5799-5808.
32. Van de Wiele, C., Dumont, F., Vanden Broecke, R., Oosterlinck, W., Cocquyt, V., Serreyn, R., Peers, S., Thornback, J., Slegers, G., and Dierckx, R. A. (2000) Technetium-99m RP-527, a GRP analogue for visualization of GRP receptor-expressing malignancies: a feasibility study. Eur. J. Nucl. Med. 27, 1694-1699.
33. 99mTc-labeling of synthetic peptides. Nucl. Med. Biol. 31, 815-820.
34. 99mTc-labeled bombesin-like peptides for early cancer detection. Anticancer Res. 26, 435-438.
35. 99mTc-labeled bombesin derivatives. Nucl. Instrum. Methods Phys. Res., Sect. A 569, 518-521.
36. Sarin, V. K., Kent, S. B. H., Tam, J. P., and Merrifield, R. B. (1981) Quantitative monitoring of solid phase peptide synthesis by the ninhydrin reaction. Anal. Biochem. 117, 147-157.
37. (V) complexes. Isot. Environ. Health Stud. 32, 21-29.
38. 99mTc-labeled bombesin-like peptide. Cancer Biother. Radiopharm. 17, 317-326.
39. Nock, B., Nikolopoulou, A., Chiotellis, E., Loudos, G., Maintas, D., Reubi, J. C., and Maina, T. (2003) [99m]Tc Demobesin 1, a novel potent bombesin analogue for GRP receptor-targeted tumor imaging. Eur. J. Nucl. Med. 30, 247-258. (Pubitemid 36686844)
40. 99mTc, Re): Synthesis, characterization, and biological behavior. Bioconjugate Chem. 16, 438-449.
41. Okarvi, S. M. (2004) Peptide-based radiopharmaceuticals: future tools for diagnostic imaging of cancers and other diseases. Med. Res. Rev. 24, 357-397. (Pubitemid 38495786)
42. Maecke, H. R. (2007) Radiolabeled peptides in Nuclear Oncology: Influence of Peptide Structure and Labeling Strategy on Pharmacology. Molecular Imaging. Volume 49: An Essential Tool in Preclinical Research, Diagnostic Imaging and Therapy (Bogdanor, A. A., Jr., Licha, K., Eds.) pp. 43-72, Chapter 10, Springer, Berlin, Germany.
43. Prasanphanich, A. F., Lane, S. R., Figueroa, S. D., Ma, L., Rold, T. L., Sieckman, G. L., Hoffman, T. J., McCrate, J. M., and Smith, C. J. (2007) The effects of linking substituents on the in vivo behavior of site-directed, peptide-based, diagnostic radiopharmaceuticals. In Vivo 21, 1-16. (Pubitemid 46359193)
44. Karra, S. R., Schibli, R., Gali, H., Katti, K. V., Hoffman, T. J., Higginbotham, C., Sieckman, G. L., and Volkert, W. A. (1999) 99mTc-Labeling and in vivo studies of a bombesin analogue with a novel water-soluble dithiaphosphine-based bifunctional chelating agent. Bioconjugate Chem. 10, 254-260. (Pubitemid 29147729)
45. 99mTc-labeled peptides. Q. J. Nucl. Med. 46, 195-205.
46. Faintuch, B. L., Teodoro, R., Duatti, A., Muramoto, E., Faintuch, S., and Smith, C. J. (2008) Radiolabeled bombesin analogs for prostate cancer diagnosis: preclinical studies. Nucl. Med. Biol. 35, 401-411.
47. 18F-labeling, and in vitro and in vivo studies of bombesin peptides modified with silicon-based building blocks. Bioconjugate Chem. 19, 1871-1879.
48. 3]-labeled bombesin analogues for improved targeting of Gastrin-releasing peptide receptor positive tumors. Bioconjugate Chem. 19, 2432-2439.
49. Abd-Elgaliel, W. R., Gallazzi, F., Garrison, J. C., Rold, T. L., Sieckman, G. L., Figueroa, S. D., Hoffman, T. J., and Lever, S. Z. (2008) Design, synthesis and biological evaluation of an antagonist-bombesin analogue as targeting vector. Bioconjugate Chem. 19, 2040-2048.
50. 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 imaging. J. Nucl. Med. 49, 318-326.
51. Lambert, B., Cybulla, M., Weiner, S. M., Van De Wiele, C., Ham, H., Dierckx, R. A., and Otte, A. (2004) Renal toxicity after radionuclide therapy. Radiat. Res. 161, 607-611. (Pubitemid 40754231)
52. Behe, M., Kluge, G., Becker, W., Gotthardt, M., and Behr, T. M. (2005) Use of polyglutamic acids to reduce uptake of radiometal-labeled minigastrin in the kidneys. J. Nucl. Med. 46, 1012-1015. (Pubitemid 43733517)
53. 3]-core. Bioconjugate Chem. 19, 2409-2416.
54. Akizawa, H., Uehara, T., and Arano, Y. (2008) Renal uptake and metabolism of radiopharmaceuticals derived from peptides and proteins. Adv. Drug Delivery Rev. 60, 1319-1328.
55. 111In-DTPA-conjugated peptides. Nucl. Med. Biol. 28, 761-768.
56. Chapman, A. P. (2002) PEGylated antibodies and antibody fragments for improved therapy: a review. Adv. Drug Delivery Rev. 54, 531-545. (Pubitemid 34615547)