Nuclear Medicine and Biology
Volume 33, Issue 5 , Pages 625-634 , July 2006

Pyrazolyl conjugates of bombesin: a new tridentate ligand framework for the stabilization of fac-[M(CO)3]+ moiety

  • Susana Alves

      Affiliations

    • Departamento de Química, Instituto Tecnológico e Nuclear, 2686-953 Sacavém, Portugal
    • ,
  • Joao D.G. Correia

      Affiliations

    • Departamento de Química, Instituto Tecnológico e Nuclear, 2686-953 Sacavém, Portugal
    • ,
  • Isabel Santos

      Affiliations

    • Departamento de Química, Instituto Tecnológico e Nuclear, 2686-953 Sacavém, Portugal
    • ,
  • Bhadrasetty Veerendra

      Affiliations

    • Department of Radiology, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Gary L. Sieckman

      Affiliations

    • Research Division, Harry S. Truman Memorial Veterans' Hospital, Columbia, MO 65201, USA
    • ,
  • Timothy J. Hoffman

      Affiliations

    • Research Division, Harry S. Truman Memorial Veterans' Hospital, Columbia, MO 65201, USA
    • Department of Internal Medicine, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • The Radiopharmaceutical Sciences Institute, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Tammy L. Rold

      Affiliations

    • Department of Internal Medicine, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Said Daibes Figueroa

      Affiliations

    • The Radiopharmaceutical Sciences Institute, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Lauren Retzloff

      Affiliations

    • Department of Radiology, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Joseph McCrate

      Affiliations

    • Department of Radiology, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Adam Prasanphanich

      Affiliations

    • Department of Radiology, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • ,
  • Charles J. Smith

      Affiliations

    • Department of Radiology, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • University of Missouri Research Reactor Center, University of Missouri-Columbia, Columbia, MO 65211, USA
    • Research Division, Harry S. Truman Memorial Veterans' Hospital, Columbia, MO 65201, USA
    • Department of Internal Medicine, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • The Radiopharmaceutical Sciences Institute, University of Missouri-Columbia School of Medicine, Columbia, MO 65211, USA
    • Corresponding Author InformationCorresponding author. Harry S. Truman Memorial VA Hospital, Research Service Room A005, 800 Hospital Drive, Columbia, MO 65201, USA. Tel.: +1 573 814 6000x3683; fax: +1 573 882 1663.

Received 1 November 2005 ,Revised 28 February 2006 ,Accepted 17 March 2006.

References 

  1. Smith CJ, Volkert WA, Hoffman TJ. Radiolabeled peptide conjugates for targeting of the bombesin receptor superfamily subtypes. Nucl Med Biol. 2005;32:733–740
  2. Smith CJ, Volkert WA, Hoffman TJ. Gastrin releasing peptide (GRP) receptor targeted radiopharmaceuticals: a concise update. Nucl Med Biol. 2003;30:861–868
  3. Giblin MF, Veerendra B, Smith CJ. Radiometallation of receptor-specific peptides for diagnosis and treatment of human cancer. In Vivo. 2005;19:9–30
  4. Rogers BE, Brechbiel MW, Kirkman RL, Clarkson M, Buchsbaum DJ. In vitro binding and internalization of an Indium-111 labeled bombesin derivative to cells expressing the gastrin releasing peptide receptor. In:  Nicolini M,  Mazzi U editor. Technetium, rhenium and other metals in chemistry and nuclear medicine. Italy: SGE Editoriali; 1999;p. 519–525
  5. Breeman WAP, Hofland LJ, DeJong M, Bernard BF, Srinivasan A, Kweekeboom DJ, et al. Evaluation of radiolabelled bombesin analogues for receptor-targeted scintigraphy and radiotherapy. Int J Cancer. 1999;81:658–665
  6. Anderson CJ, Welch MJ. Radiometal-labeled agents (non-technetium) for diagnostic imaging. Chem Rev. 1999;99:2219–2234
  7. Gali H, Hoffman TJ, Sieckman GL, Owen NK, Katti KV, Volkert WA. Synthesis, characterization, and labeling with 99mTc/188Re of peptide conjugates containing a dithia-bisphosphine chelating agent. Bioconjug Chem. 2001;12:354–363
  8. Karra SR, Schibli R, Gali H, Katti KV, Hoffman TJ, Higginbotham C, et al. 99mTc-labeling and in vivo studies of a bombesin analogue with a novel water-soluble dithiadiphosphine-based bifunctional chelating agent. Bioconjug Chem. 1999;10:254–260
  9. Lantry LE, Thomas R, Waser B, Maddalena M, Fox JS, Arunachalam T, et al. Preclinical evaluation of 177Lu-AMBA, a DOTA conjugate that targets GRP and NMB receptor expressing tumors: internalization, in vivo biodistribution, single dose radiotherapy in PC-3 tumor-bearing nude mice and in vitro autoradiograpy in animal and human tissues. Helsinki, Finland: EANM; 2004;
  10. Zhang H, Chen J, Waldherr C, Hinni K, Waser B, Reubi JC, et al. 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. 2004;64:6707–6715
  11. Alves S, Paulo A, Correia JDG, Domingos Â, Santos I. Coordination capabilities of pyrazolyl containing ligands towards the fac-[Re(CO)3]+ moiety. J Chem Soc, Dalton Trans. 2002;24:4714–4719
  12. Alves S, Paulo A, Correia JDG, Gano L, Santos I. New building blocks for labeling peptides with the [99mTc(CO)3]+ core. In:  Nicolini U,  Mazzi SG editor. Technetium, rhenium and other metals in chemistry and nuclear medicine 6. Padova: Editoriali; 2002;p. 139–142
  13. Vitor R, Alves S, Correia JDG, Paulo A, Santos I. Rhenium (I)- and technetium(I) tricarbonyl complexes anchored by bifunctional pyrazole-diamine and pyrazole-dithioether chelators. J Organomet Chem. 2004;689:4764–4774
  14. Alves S, Paulo A, Correia JDG, Gano L, Smith CJ, Hoffman TJ, et al. Pyrazolyl derivatives as bifunctional chelators for labeling tumor-seeking peptides with the fac-[M(CO)3]+ moiety (M=99mTc, Re): synthesis, characterization, and biological behavior. Bioconjug Chem. 2005;16:438–449
  15. La Bella R, Garcia-Garayoa E, Langer M, Blauestein P, Beck-Sickinger AG, Schubiger PA. 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
  16. Alberto R, Herrmann WA, Kiprof P, Baumgartner F. Multiple bonds between main group elements and transition metals. Synthesis and reactivity of TcCl(CO)3[P(C6H5)3]2: novel technetium complexes of 1,4,7-triazacyclononane and hydridotris(pyrazolyl)borate. Inorg Chem. 1992;31:895–899
  17. Alberto R, Schibli R, Schubiger PA. Reactions with the technetium and rhenium carbonyl complexes (NEt4)2[MX3(CO)3]. Synthesis and structure of [Tc(CN-But)3(CO)3](NO3) and (NEt)4[Tc2(μ-SCH2CH2OH)3(CO)6]. Polyhedron. 1996;15(7):1079–1089
  18. Alberto R, Schibli R, Abram U, Egli A, Knapp FF, Schubiger PA. Potential of the “[M(CO)3]+” (M=Re, Tc) moiety for the labeling of biomolecules. Radiochim Acta. 1997;79:99–103
  19. Reigys M, Wust F, Alberto R, Schibli R, Schubiger PA, Pietzsch HJ, et al. Synthesis of rhenium(I) and technetium(I) carbonyl/dithioether ligand complexes bearing 3,17β-estradiol. Biorg Med Chem Lett. 1997;17:2243–2246
  20. Pietzsch HJ, Reisgys M, Alberto R, Hoepping A, Scheunemann M, Seifert S, et al. Thioether ligands as anchor groups for coupling the “Tc(CO)3” and “Re(CO)3” moieties with biologically active molecules. In:  Nicolini M,  Ulderico M editor. Technetium, rhenium and other metals in chemistry and nuclear medicine. Italy: SGE; 1999;p. 313–316
  21. Egli A, Alberto R, Tannahill L, Schibli R, Abram U, Schaffland A, et al. [99mTc(OH2)3(CO)3]+ labels peptide to an unprecedented high specific activity. A labelling study with amino acids and neurotensin. In:  Nicolini M,  Ulderico M editor. Technetium, rhenium and other metals in chemistry and nuclear medicine. Italy: SGE; 1999;p. 507–512
  22. Smith CJ, Sieckman GL, Owen NK, Hayes DL, Mazuru DG, Kannan R, et al. Radiochemical investigations of GRP receptor-specific [99mTc(X)(CO)3-Dpr-Ser-Ser-Ser-Gln-Trp-Ala-Val-Gly-His-Leu-Met-(NH2)]: in PC3, tumor-bearing, rodent models: syntheses, radiolabeling, and in vitro/in vivo studies where Dpr=2,3-diaminopropionic acid and X=H2O or P(CH2OH)3. Cancer Res. 2003;63:4082–4088
  23. Smith CJ, Sieckman GL, Owen NK, Hayes DL, Mazuru DG, Volkert WA, et al. Radiochemical investigations of [188Re(H2O(CO)3-diaminopropionic acid-SSS-bombesin(7–14)NH2]: syntheses, radiolabeling and in vitro/in vivo GRP receptor targeting studies. Anticancer Res. 2003;23:63–70
  24. Smith CJ, Gali H, Sieckman GL, Higginbothman C, Volkert WA, Hoffman TJ. Radiochemical investigations of 99mTc-N3S-X-BBN[7–14]NH2: an in vitro/in vivo structure–activity relationship study where X=0, 3, 5, 8, and 11-carbon tethering moieties. Bioconjug Chem. 2003;14:93–102
  25. Faintuch BL, Santos RLSR, Souza ALFM, Hoffman TJ, Greeley M, Smith CJ. 99mTc-HYNIC-bombesin(7–14)NH2: radiochemical evaluation with co-ligands EDDA (EDDA=ethylenediamine-N,N′-diacetic acid), tricine, and nicotinic acid. Synth React Inorg Met Org Nanomet Chem. 2005;35:43–51
  26. Smith CJ, Gali H, Sieckman GL, et al. Radiochemical investigations of 177Lu-DOTA-8-AOC-BBN(7–14)NH2: an in vitro/in vivo assessment of the targeting ability of this new radiopharmaceutical for PC-3 human prostate cancer cells. Nucl Med Biol. 2003;30(2):101–109
  27. Decristoforo C, Mather SJ. The influence of chelator on the pharmacokinetics of 99mTc-labeled peptides. Q J Nucl Med. 2002;46:195–205
  28. Liu S, Edwards DS. 99mTc-labeled peptides small peptides as diagnostic radiopharmaceuticals. Chem Rev. 1999;99:2235–2268
  29. Schuhmacher J, Zhang H, Doll J, Macke HR, Matys R, Hauser H, et al. GRP receptor-targeted PET of a rat pancreas carcinoma xenograft in nude mice with a 68Ga-labeled bombesin(6–14) analog. J Nucl Med. 2005;46(4):691–699
  30. Press OW, Shan D, Howell-Clark J, Eary J, Appelbaum FR, Matthews D, et al. Comparative metabolism and retention of iodine-125, yttrium-90, and indium-111 radioimmunoconjugates by cancer cells. Cancer Res. 1996;56:2123–2129
  31. Fleischmann A, Laderach U, Friess H, Buechler MW, Reubi JC. Bombesin receptors in distinct tissue compartments of human pancreatic diseases. Lab Invest. 2000;80(12):1807–1817
  32. Sano H, Feighner SD, Hreniuk DL, Iwaasa H, Sailer AW, Pan J, et al. Characterization of the bombesin-like peptide receptor family in primates. Genomics. 2004;84:139–146
  33. Van De Wiele C, Dumont F, Van Belle S, Slegers G, Peers SH, Dierckx RA. Is there a role for agonist gastrin-releasing peptide receptor radioligands in tumor imaging?. Nucl Med Commun. 2001;22:5–15
  34. Nock B, Nikolopoulou A, Chiotellis E, Loudos G, Maintas D, Reubi JC, et al. [99mTc]Demobesin 1, a novel potent bombesin analogue for GRP receptor-targeted tumour imaging. Eur J Nucl Med. 2003;30(2):247–258
  35. Nock B, Nikolopoulou A, Galanis A, Cordopatis P, Waser B, Reubi JC, et al. Potent bombesin-like peptides for GRP-receptor targeting of tumors with 99mTc: a preclinical study. J Med Chem. 2005;48(1):100–110
  36. Van de Wiele C, Dumont F, Broecke RV, Oosterlinck W, Cocquyt V, Serreyn R, et al. Technetium-99 m RP525, a GRP analogue for visualization of GRP receptor-expressing malignancies: a feasible study. Eur J Nucl Med. 2000;27:1694–1699
  37. Baidoo KE, Lin K-S, Zhan Y, Finley P, Scheffel U, Wagner HN. Design, synthesis, and initial evaluation of high-affinity technetium bombesin analogues. Bioconjug Chem. 1998;9:218–225
  38. Nock B, Nikolopoulou A, Chiotellis E, Loudos G, Maintas D, Reubi JC, et al. [99mTc]Demobesin 1, a novel potent bombesin analogue for GRP receptor-targeted tumour imaging. Eur J Nucl Med. 2003;30(2):247–258
  39. Maina T, Nock BA, Zhang H, Nikolopoulou A, Waser B, Reubi J-C, et al. Species differences of bombesin analog interactions with GRP-R define the choice of animal models in the development of GRP-R-targeting drugs. J Nucl Med. 2005;46:823–830
  40. Benya RV, Kusui T, Pradhan TK, Battey JF, Jensen RT. Expression and characterization of cloned human bombesin receptors. Mol Pharmacol. 1995;47:10–20
  41. Hoffman TJ, Gali H, Smith CJ, Sieckman GL, Hayes DL, Owen NK, et al. Novel series of 111In-labeled bombesin analogs as potential radiopharmaceuticals for specific targeting of gastrin-releasing peptide receptors expressed on human prostate cancer cells. J Nucl Med. 2003;44:823–831

PII: S0969-8051(06)00064-3

doi: 10.1016/j.nucmedbio.2006.03.007

Nuclear Medicine and Biology
Volume 33, Issue 5 , Pages 625-634 , July 2006

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