188Re- and 99mTc-MAG3 as prosthetic groups for labeling amines and peptides: Approaches with pre- and postconjugate labeling

Nuclear Medicine and Biology

Volumn 25, Issue 7, 1998, Pages 621-631

  Guhlke, S ^a   Schaffland, A ^a   Zamora, P O ^a,b   Sartor, J ^a   Diekmann, D ^a   Bender, H ^a   Knapp, F F ^c   Biersack, H J ^a  

^a UNIVERSITY OF BONN   (Germany)

^b RhoMed Inc   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

MAG3 peptides; MAG3 RC 160; RC 160; Rhenium 188; Somatostatin; Technetium 99m

Indexed keywords

MERTIATIDE TC 99M; RHENIUM 188; SOMATOSTATIN; VAPREOTIDE; 1,6 HEXANEDIAMINE; 1,6-DIAMINOHEXANE; AMINE; DIAMINE; DRUG DERIVATIVE; FORMIC ACID DERIVATIVE; OLIGOPEPTIDE; ORGANOMETALLIC COMPOUND; RADIOPHARMACEUTICAL AGENT; RHENIUM MERCAPTOACETYLTRIGLYCINE; RHENIUM-MERCAPTOACETYLTRIGLYCINE; T BUTYLOXYCARBONYL GROUP; T-BUTYLOXYCARBONYL GROUP; TECHNETIUM COMPLEX;

ANIMAL EXPERIMENT; ARTICLE; CONJUGATION; DRUG DISTRIBUTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOTOPE LABELING; LIVER METABOLISM; MOUSE; PLASMA CLEARANCE; PROTEIN DETERMINATION; ANIMAL; CHEMISTRY; FEMALE; NUDE MOUSE; TIME; TISSUE DISTRIBUTION;

AMINES; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIAMINES; FEMALE; FORMIC ACID ESTERS; MICE; MICE, NUDE; OLIGOPEPTIDES; ORGANOMETALLIC COMPOUNDS; ORGANOTECHNETIUM COMPOUNDS; RADIOPHARMACEUTICALS; SOMATOSTATIN; TECHNETIUM TC 99M MERTIATIDE; TIME FACTORS; TISSUE DISTRIBUTION;

EID: 0031593890     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(98)00025-0     Document Type: Article

References (35)

1. 99m-labeled chemotactic peptides Comparison with indium-111-labeled white blood cells for localizing acute bacterial infection in rabbit . J. Nucl. Med. 34:1993;2176-2181.
2. 3]octreotide . Eur. J. Nucl. Med. 20:1993;1089-1094.
3. 1]octreotide . Eur. J. Nucl. Med. 21:1994;328-335.
4. 161Tb-DTPA-octreotide, a somatostatin analogue with potential for intraoperative scanning and radiotherapy. Eur. J. Nucl. Med. 22:1995;608-616.
5. Deutsch E., Libson K., Vanderheyden J.-L., Ketring A.R., Maxon H.R. The chemistry of rhenium and technetium as related to the use of isotopes of these elements in therapeutic and diagnostic nuclear medicine. Nucl. Med. Biol. 13:1986;465-477.
6. Fischman A.J., Rauh D., Solomon H., Babich W., Tompkins R.G., Kroon D., et al. In vivo bioactivity and biodistribution of chemotactic peptide analogs in nonhuman primates. J. Nucl. Med. 34:1993;2130-2134.
7. 3 as a hippuran replacement. J. Nucl. Med. 27:1986;111-116.
8. 18F]fluorocarboxylic acids. Appl. Radiat. Isot. 45:1994;715-727.
9. 188Re labelling of amines and peptides. Nicolini M., Bandoli G., Mazzi U. Technetium and Rhenium in Chemistry and Nuclear Medicine. Vol. 4:1995;363-366 Editoriali, Padua, Italy.
10. 1)-octreotide, a potential radiopharmaceutical for quantitative somatostatin receptor imaging with PET Synthesis, radiolabeling, in vitro validation and biodistribution in mice . Nucl. Med. Biol. 21:1994;819-825.
11. Hosono M., Hosono M.N., Haberberger T., Zamora P.O., Gulhke S., Bender H., et al. Targeting of small-cell lung cancer by octreotide labeled with I-125, In-111, and Re-188 in a mouse model. Jpn. J. Cancer Res. 87:1996;995-1000.
12. Jeong J.M., Kinuga S., Paik C.H., Saga T., Sood J.A., Carrasquillo J.A., et al. Application of high-affinity binding concept to radiolabel avidin with Tc-99m-labeled biotin and the effect of pI on biodistribution. Nucl. Med. Biol. 21:1994;935-940.
13. Johnson P., Lock C.J.L., Wilkinson G. Amine, phosphine, arsine and stibine complexes of rhenium-(III), -(IV) and -(V). J. Chem. Soc. 1964;1054-1066.
14. Knapp F.F. Jr, Mirzadeh S., Beets A.L., Sharkey R., Griffiths G., Juweid M., et al. Curie-scale tungsten-188/rhenium generators for routine clinical applications. Nicolini M., Bandoli G., Mazzi U. Technetium and Rhenium in Chemistry and Nuclear Medicine. 4:1995;319-324 Editoriali, Padua, Italy.
15. Knapp F.F. Jr, Mirzadeh S. The continuing important role of radionuclide generator systems for nuclear medicine. Invited Review Article, Eur. J. Nucl Med. 21:1994;1151-1166.
16. Knapp F.F. Jr, Callahan A.P., Beets A.L., Mirzadeh S., Hsieh B.-T. Processing of reactor-produced tungsten-188 for fabrication of clinical scale alumina-based tungsten-188/rhenium-188 generators. Appl. Rad. and Isot. 45:1994;1123-1128.
17. König W., Geiger R. N-Hydroxyverbindungen als katalysatoren fur die aminolyse aktivierter ester. Chem. Ber. 106:1973;3626-3635.
18. 3]-octreotide The Rotterdam experience with more than 1,000 patients . Eur. J. Nucl. Med. 20:1993;716-731.
19. 99mTc-chelator-peptide conjugates . Bioconjug. Chem. 7:1996;196-202.
20. Maina T., Stolz B., Albert R., Bruns C., Koch P., Mäcke H. Synthesis, radiochemistry and biological evaluation of a new somatostatin analogue (SDZ 219-387) labelled with technetium-99m. Eur. J. Nucl. Med. 21:1994;437-444.
21. 3 starting from S-unprotected mercaptoacetyltriglycine. Appl. Radiat. Isot. 43:1992;899-901.
22. Nutt R.F., Verber D.F., Curely P.E., Saperstein R., Hirschmann R. Somatostatin analogs which define the role of the lysine-9 amino group. Int. J. Pept. Protein Res. 21:1983;66-73.
23. Perrin D. D. (Ed.) (1965) Dissociation Constants of Organic Bases in Aqueous Solution. Butterworth, London.
24. Pinski J., Schally A.V., Halmos G. Effect of somatostatin analog RC-160 and bombesin/gastrin releasing peptide antagonist RC-3095 on growth of PC-3 human prostate cancer xenografts in nude mice. Int. J. Cancer. 55:1993;963-967.
25. 3 chelate. J. Label. Compd. Radiopharm. (in press).
26. Srinivasan A. et al. (1991) United States Patent, Patent Number: 4,988,496.
27. Steglich W., Höfle G. 4-Dialkylaminopyridine as highly active acylation catalysts. Angewandte Chemie Int. Ed. 8:1969;981-984.
28. Stolz B., Smith-Jones P.M., Albert R., Reist H., Macke H., Bruns C. Biological characterization of [Ga-67] or [Ga-68] labeled DFO-octreotide (SDZ-216-927) for PET studies of somatostatin receptor-positive tumors. Horm. Metab. Res. 26:1994;453-459.
29. Thakur M.L., Kolan H.R., Duggaraju R., Halmos G., Schally A. Imaging breast cancer with Tc-99m-somatostatin analogs RC-160 and sandostatin Comparison with In-111 octreotide . Radiology. 47:1995;320. (Abstract).
30. 18F]fluorobenzoate and its application to the labeling of a monoclonal antibody fragment. Bioconjug. Chem. 5:1994;352-356.
31. Van Gog F.B., Visser G.W.M., Klok R., Van der Schors R., Snow G.B., van Dongen G.A.M.S. Monoclonal antibodies labeled with rhenium-186 using the MAG3 chelate Relationship between the number of chelated groups and biodistribution characteristics . J. Nucl. Med. 37:1996;352-362.
32. 1H-NMR and computer modeling conformational analysis . J. Biol. Chem. 269:1994;12583-12588.
33. Visser G.W., Gerretsen M., Herscheid J.D., Snow G.S., van Dongen G. Labeling of monoclonal antibodies with rhenium-186 using the MAG3 chelate for radioimmunotherapy of cancer A technical protocol . J. Nucl. Med. 34:1993;1953-1963.
34. Wester H. J., Hamacher K. and Stöcklin G (in press) A comparative study of N.C.A. fluorine-18 labeling of proteins via acylation and photochemical conjugation. Nucl. Med. Biol.
35. 188Re-RC-160, a directly radiolabeled somatostatin analogue. Int. J. Cancer. 65:1996;1-8.