Assessment of the best N3- donors in preparation of [M(N)(PNP)]-based (M=99mTc-; 188Re) target-specific radiopharmaceuticals: Comparison among succinic dihydrazide (SDH), N-methyl-S-methyl dithiocarbazate (HDTCZ) and PEGylated N-methyl-S-methyl dithiocarbazate (HO2C-PEG600-DTCZ)

Nuclear Medicine and Biology

Volumn 41, Issue 7, 2014, Pages 570-581

  Carta, Davide ^a   Jentschel, Christian ^b   Thieme, Stefan ^b   Salvarese, Nicola ^a   Morellato, Nicolò ^a   Refosco, Fiorenzo ^c   Ruzza, Paolo ^c   Bergmann, Ralf ^b   Pietzsch, Hans Jurgen ^b   Bolzati, Cristina ^c  

^a UNIVERSITY OF PADOVA   (Italy)

^b INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

^c CNR   (Italy)

Author keywords

Diphosphinoamines; Peptide; Rhenium; Technetium; Therapy

Indexed keywords

AMINODIPHOSPHINE; CHELATING AGENT; CYSTEINE DERIVATIVE; HYDRAZIDE DERIVATIVE; LIGAND; MACROGOL 6000; N METHYL S METHYLDITHIOCARBAZATE; NITROGEN; NITROGEN 3; PEGYLATED N METHYL S METHYLDITHIOCARBAZATE; PHOSPHINE DERIVATIVE; PROTON; REAGENT; RHENIUM 188; SUCCINIC DIHYDRAZIDE; TECHNETIUM 99M; UNCLASSIFIED DRUG; HYDRAZINE DERIVATIVE; RADIOISOTOPE; RADIOPHARMACEUTICAL AGENT; RHENIUM; SUCCINIC ACID DERIVATIVE; TECHNETIUM COMPLEX;

ANALYZER; ANIMAL EXPERIMENT; ARTICLE; CHEMICAL REACTION; DRUG DETERMINATION; DRUG PURIFICATION; DRUG SYNTHESIS; DRUG TARGETING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOCHEMISTRY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; ANIMAL; CHEMISTRY; COMPARATIVE STUDY; DIAGNOSTIC USE; DRUG STABILITY; METABOLISM; RAT; SYNTHESIS;

ANIMALS; DRUG STABILITY; HYDRAZINES; MALE; MICE; NITROGEN; ORGANOTECHNETIUM COMPOUNDS; RADIOISOTOPES; RADIOPHARMACEUTICALS; RATS; RHENIUM; SUCCINATES; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 84904440421     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2014.04.126     Document Type: Article

References (28)

1. Knapp F.F., Callahan A.P., Beets A.L., Mirzadeh S., Hsieh B.T. Processing of reactor-produced W-188 for fabrication of clinical-scale alumina based W-188/Re-188 generators. Appl Radiat Isot 1994, 45:1123-1128.
2. 188Re-pharmaceuticals. Adv Drug Deliv Rev 2008, 60:1389-1401.
3. 99mTc-radiopharmaceuticals containing the TcN multiple bond. Int J Appl Radiat Isot 1992, 43:1329-1333.
4. 2] (NOEt=N-ethyl-nethoxydithiocarbamato). J Chem Soc Chem Commun 1992, 1354-1355.
5. 186Re nitrido complexes, technetium, rhenium and other metals in chemistry and nuclear medicine 1999, 5:149-152. SGE Editoriali, Italy. M. Nicolini, U. Mazzi (Eds.).
6. -. Nucl Med Biol 2003, 30:381-387.
7. 188Re(N)-based target-specific radiopharmaceuticals. Nucl Med Biol 2011, 38:399-415.
8. Boschi A., Massi A., Uccelli L., Pasquali M., Duatti A. PEGylated N-methyl-S-methyl dithiocarbazate as a new reagent for the high-yield preparation of nitrido Tc-99m and Re-188 radiopharmaceuticals. Nucl Med Biol 2010, 37:927-934.
9. Bolzati C., Caporale A., Agostini S., Carta D., Cavazza-Ceccato M., Refosco F., et al. Avidin-biotin system: a small library of cysteine biotinylated derivatives designed for the [99mTc(N)(PNP)]2+ metal fragment. Nucl Med Biol 2007, 34:511-522.
10. Biondi B., Bolzati C., Carta D., Salvarese N., Refosco F., Calderan A., et al. The [Tc(N)PNP] metal fragment labeled peptide for mc1 receptors imaging: preliminary studies. J Pept Sci 2010, 16:182.
11. + complex (DTC-Ln=alicyclic dithiocarbamate and PNP=diphosphinoamine). Bioconjug Chem 2010, 21:928-939.
12. Duatti A., Marchi A., Pasqualini R. Formation of the TcN multiple bond from the reaction of ammonium pertechnetate with S-methyl dithiocarbazate and its application to the preparation of Tc-99m radiopharmaceuticals. J Chem Soc Dalton Trans 1990, 3729-3733.
13. + (M=Tc-99, Re; DTC=dithiocarbamate; PNP=heterodiphosphane). Eur J Inorg Chem 2004, 9:1902-1913.
14. 2+ (PXP=diphosphine ligand). A novel tool for the selective labeling of small molecules. J Am Chem Soc 2002, 124:11468-11479.
15. Bellande E., Comazzi V., Pasqualini R., Duatti A. Development of a kit formulation for the synthesis of the TcN multiple bond a tracer level. Technetium and Rhenium in Chemistry and Nuclear Medicine 1994, 4:329-342. SGE Editoriali, Italy. M. Nicolini, G. Bandoli, U. Mazzi (Eds.).
16. 2+ (PXP=diphosphine ligand). Bioconjug Chem 2001, 12:1035-1042.
17. 2+ core towards shiff bases derived from S-methyl dithiocarbazate. Crystal structures of [S-methyl 3-(2-hydroxyphenyl-methylene)dithiocarbazato]nitrido (triphenylphosphine)technetium(V) and bis (S-methyl 3-isopropylidenedithiocarbazato)nitridotecnetium(V). J Chem Soc Dalton Trans 1988, 1743-1749.
18. Baldas J., Bonnyman J., Williams G.A. Studies of technetium complexes. Use of the tetrachloronitridotechnetate(VI) anion for the preparation of nitrido complexes of technetium. Crystal structure of bis(8-quinolinethiolato)nitridotechnetium(V). Inorg Chem 1986, 25:150-155.
19. Duatti A., Marchi A., Pasqualini R. Formation of the TcN multiple bond from the reaction of ammonium pertechnetate with S-methyl dithiocarbazate and its application to the preparation of technetium-99m radiopharmaceuticals. J Chem Soc Dalton Trans 1990, 3729-3733.
20. 2+ (M=Tc or Re) species. J Chem Soc Dalton Trans 1996, 3105-3109.
21. 2]. J Chem Soc Dalton Trans 1995, 1357-1361.
22. Mévellec F., Roucoux A., Noiret N., Patin H., Toupet L. Synthesis, spectroscopic studies and molecular structure of original halogeno-[S-methyl 3-(2-hydroxyphenylethylidene)dithiocarbazato]oxo-rhenium(V) complexes. Polyhedron 1999, 18:2537-2541.
23. Mévellec F., Roucoux A., Noiret N., Patin H. Synthesis, properties and spectroscopic studies of rhenium(V) complexes stabilized by tridentate Schiff bases derived from S-methyl dithiocarbazate. J Chem Soc Dalton Trans 2001, 3603-3610.
24. Mévellec F., Lepareur N., Roucoux A., Noiret N., Patin H., Bandoli G., et al. Chelated hydrazido(3-)rhenium(V) complexes: on the way to the nitrido-M(V) core (M=Tc, Re). Inorg Chem 2002, 41:1591-1597.
25. Liu S., Edwards D.S. 99mTc-labeled small peptides as diagnostic radiopharmaceutical. Chem Rev 1999, 99:2235-2268.
26. Bolzati C., Carta D., Salvarese N., Refosco F. Chelating systems for Tc-99m/Re-188 in the development of radiolabeled peptide pharmaceuticals. Anti Cancer Agents Med Chem 2012, 12:428-461.
27. 188Re: a potential strategy for diagnosis and therapy of folate receptor positive tumors. Nucl Med Biol 2007, 34:595-601.
28. Howell R.C., Revskaya E., Pazo V., Nosanchuk J.D., Casadevall A., Dadachova E. Phage display library derived peptides that bind to human tumor melanin as potential vehicle therapy of metastatic melanoma. Bioconjug Chem 2007, 18:1739-1748.