Neurotensin(8-13) analogue: Radiolabeling and biological evaluation using different chelators

Nuclear Medicine and Biology

Volumn 38, Issue 1, 2011, Pages 113-120

  Teodoro, Rodrigo ^a   Faintuch, Bluma Linkowski ^a   Núñez, Eutimio Gustavo Fernández ^a   Queiróz, Rodrigo Guimarães ^a  

^a INSTITUTO DE PESQUISAS ENERGÉTICAS E NUCLEARES   (Brazil)

Author keywords

99mTc; Bifunctional chelating agents; Neurotensin analog

Indexed keywords

CHELATING AGENT; CYSTEINE; GLUTATHIONE; NEUROTENSIN[8-13] TC 99M; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BLOOD; BONE; COMPLEX FORMATION; CONJUGATION; CONTROLLED STUDY; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG SCREENING; DRUG STABILITY; DRUG UPTAKE; FEMALE; IN VITRO STUDY; INTESTINE; ISOTOPE LABELING; LIPOPHILICITY; LIVER; MOUSE; MUSCLE; NONHUMAN; PARTITION COEFFICIENT; PLASMA PROTEIN BINDING; RADIOCHEMISTRY; SWISS WEBSTER MOUSE;

ANIMALS; BLOOD PROTEINS; CHELATING AGENTS; CROSS-LINKING REAGENTS; CYSTEINE; DRUG STABILITY; FEMALE; GLUTATHIONE; HYDRAZINES; ISOTOPE LABELING; MICE; NEUROTENSIN; NICOTINIC ACIDS; OLIGOPEPTIDES; ORGANOTECHNETIUM COMPOUNDS; PEPTIDE FRAGMENTS; RADIOCHEMISTRY; SUCCINIMIDES;

EID: 78650976906     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2010.06.011     Document Type: Article

References (34)

1. Shuang L. Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides. Adv Drug Deliv Rev 2008, 60(12):1347-1370.
2. Vanderheyden J., Liu G., He J., Patel B., Tait J.F., Hnatowich D.J. Evaluation of 99mTc-MAG3-annexin V: influence of the chelate on in vitro and in vivo properties in mice. Nucl Med Biol 2006, 33:135-144.
3. Mardirossian G., Wu C., Ruscowski M., Hantowich D.J. The stability of technetium-99m directly labeled to a Fab′ antibody via stannous ion and mercaptoethanol reduction. Nucl Med Commun 1992, 13:503-512.
4. Zhang Y.M., Liu N., Zhu Z.H., Ruscowski M., Hnatowich D.J. Influence of different chelators (HYNIC, MAG3 AND DTPA) on tumor cell accumulation and mouse biodistribution of technetium-99m labeled to antisense DNA. Eur J Nucl Med 2000, 27:1700-1707.
5. Abrams M.J., Juweid M., tenKate C.I., Schwartz D.A., Hauser M.M., Gaul F.E., et al. Technetium-99m-human polyclonal IgG radiolabeled via the hydrazino nicotinamide derivative for imaging focal sites of infection in rats. J Nucl Med 1990, 31:2022-2028.
6. Biechlin M., Bonmrtin A., Gilly F., Fraysse M., d'Hardemare A.M. Radiolabeling of annexin A5 with 99mTc: comparison of HYNIC-TC vs iminothiolane-Tc-tricarbonyl conjugates. Nucl Med and Biol 2008, 35:679-687.
7. Ono M., Arano Y., Uehara T., Fujioka Y., Ogawa K., Namba S., et al. Intracellular metabolic fate of radioactivity after injection of technetium-99m-labeled hydrazino nicotinamide derivatized proteins. Bioconjug Chem 1999, 10:386-394.
8. Liu S., Edwards D.S., Looby R.J., Harris A.R., Poirer M.J., Barrett J.A., et al. Labeling a hydrazino nicotinamide-modified cyclic IIb/IIa receptor antagonist with 99mTc using aminocarboxylates as coligands. Bioconjug Chem 1996, 7:63-71.
9. Liu S., Edwards D.S., Harris A.R. A novel ternary ligand system for 99mTc-labeling of hydrazino nicotinamide modified biologically active molecules using imine-N-containing heterocycles as coligands. Bioconjug Chem 1998, 9:583-595.
10. Noll B., Johannsen B., May K, Spies H. Preparation of the renal function imaging agent 99mTc-MAG3 starting from S-unprotected mercaptoacetyltriglycine. Appl Radiat Isot 1992, 43(7):899-901.
11. Duncan R.J.S., Weston P.D., Wrigglesworth R. A new reagent which may be used to introduce sulfhydryl-groups into proteins, and its use in the preparation of conjugates for immunoassay. Anal Biochem 1983, 132:68-73.
12. Winnard P., Chang F., Ruscowski M., Mardirossian G., Hnatowic D.J. Preparation and use of NHS-MAG3 for technetium-99m labeling of DNA. Nucl Med Biol 1997, 24:425-432.
13. Okarvi S.M. Peptides-based radiopharmaceuticals and cytotoxic conjugates: potential tools against cancer. Cancer Treat Rev 2008, 34(1):13-26.
14. Fichna J., Janecka A. Synthesis of target-specific radiolabeled peptides for diagnostic imaging. Bioconjug Chem 2003, 14:3-17.
15. Garcia-Garayoa E., Ruegg D., Blauesntein P., Zwimpfer M., Khan I.U., Maes V., et al. Chemical and biological characterization of new Re(CO)3/[99mTc](CO)3 bombesin analogues. Nucl Med Biol 2007, 34:17-28.
16. Carraway R.E., Leeman S.E. The isolation of a new hypotensive peptide, neurotensin, from bovine hypothalami. J Biol Chem 1973, 248:6854-6861.
17. Nock B.A., Nikolopoulou A., Reubi J., Maes V., Conrath P., Tourwe D., et al. Toward stable N4-modified neurotensins for NTS1-receptor-targeted tumor imaging with 99mTc. J Med Chem 2006, 49:4767-4776.
18. Granier C., van Rietschoten J., Kitabgi P., Poustis C., Freychet P. Synthesis and characterization of neurotensin analogues for structure/activity relationship studies - acetyl-neurotensin-(8-13) is the shortest analogue with full binding and pharmacological activities. Eur J Biochem 1982, 124:117-125.
19. Garcia-Garayoa E., Maes V., Blauestein P., Blanc A., Hohn A., Tourwe D., et al. Double-stabilized neurotensin analogues as potential radiopharmaceuticals for NTR-positive tumors. Nucl Med Biol 2006, 33:495-503.
20. La Bella R., Garcia-Garayoa E., Langer M., Blauenstein P., Beck-Sickinger A.G., Schubiger P.A. In vitro and in vivo evaluation of a 99mTc(I)-labeled bombesin analogue for imaging of gastrin releasing peptide receptor-positive tumors. Nucl Med Biol 2002, 29:553-560.
21. Faintuch B.L., Teodoro R., Duatti A., Muramoto E., Faintuch S., Smith C.J. Radiolabeling bombesin analogs for prostate cancer diagnosis: preclinical studies. Nucl Med Biol 2008, 35(4):401-411.
22. Wang Y., Liu G., Hnatowich D.J. Methods for MAG3 conjugation and 99mTc radiolabeling of biomolecules. Nature Protocols 2006, 1(3):1477-1480.
23. Buchegger F., Bonvin F., Kosinski M., Schaffland A.O., Prior J., Reubi J.C., et al. Radiolabeled neurotensin analog, 99mTc-NT-XI, evaluated in ductal pancreatic adenocarcinoma patients. J Nucl Med 2003, 44(10):1649-1654.
24. Carraway RE, Plona AM Involvement of NT in cancer growth evidences, mechanisms and development of diagnostic tolls. Peptides 2006, 27(10):2445-2460.
25. Somai S., Gompel A., Rostene W., Forgez P. Neurotensin counteracts apoptosis in breast cancer cells. Biochem Biophys Res Commun 2002, 295:482-488.
26. Einsiedel J., Hubner H., Hervt M., Harterich S., Koschatzky S., Gmeiner P. Peptide backbone modifications on the C-terminal hexapeptide of neurotensin. Bioorg Med Chem Lett 2008, 18(6):2013-2018.
27. Garcia-Garayoa E., Allemann-Tannahill L., Blauenstein P., Willmann M., Carrel-Remy N., Tourwe D., et al. In vitro and in vivo evaluation of new radiolabeled neurotensin(8-13) analogues with high affinity for NT1 receptors. Nucl Med Biol 2001, 28:75-84.
28. Hultsch C., Pawelke B., Bergmann R., Wuest F. Synthesis and evaluation of novel multimeric neurotensin(8-13) analogs. Bioorg Med Chem 2006, 14:5913-5920.
29. Liu G., Wescott C., Sato A., Wang Y., Liu N., Zhang Y., et al. Nitriles form mixed-coligand complexes with 99mTc-HYNIC-peptide. Nucl Med Biol 2002, 29:107-113.
30. Lei K., Ruscowsky M., Chang F., Qu T., Mardirossian G., Hnatowich D.J. Technetium-99m antibodies labeled with MAG3 and HYNIC - an in vitro and animal in vivo properties. Nucl Med Biol 1996, 23:917-922.
31. Verbke K., Hjeslstuden O., Debrock E., Cleythens B., De Roo M., Verbruggen A. Comparative evaluation of 99mTc-HYNIC-HAS and 99mTc-MAG3-HAS as possible blood poll agents. Nucl Med Comm 1995, 16:942-957.
32. Ono M., Arano Y., Mukai T., Uehara T., Fujioka Y., Ogawa K., et al. Plasma protein binding of 99mTc-labeled hydrazino nicotinamide derivatized polypeptides and peptides. Nucl Med Biol 2000, 28(2):155-164.
33. Decristoforo C., Mather S.J. The influence of chelator on the pharmacokinetics of 99mTc-labelled peptides. Q. J. Nucl. Med. 2002, 46:195-205.
34. Decristoforo C., Faintuch B.L., Rey A., von Guggenberg E., Rupprich M., Hernandez-Gonzales I., Haubner R., Teodoro R. [99mTc]HYNIC-RGD for imaging integrin avb3 expression. Nucl. Med. Biol. 2006, 33:945-952.