Nuclear Medicine and Biology
Volume 35, Issue 7 , Pages 747-753 , October 2008

A critical quantum chemical and experimental study of the potentiality of direct labeling of the CN group with [99mTc(CO)3]+ or [186/188Re(CO)3]+ in CN containing biomolecules

  • Benasser Safi

      Affiliations

    • General Chemistry (ALGC), Faculty of Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium
    • ,
  • John Mertens

      Affiliations

    • Radiopharmaceutical Chemistry (BEFY), Faculty of Medicine and Pharmacy, Vrije Universiteit Brussel, Laarbeeklaan 103, 1090 Brussels, Belgium
    • Corresponding Author InformationCorresponding author. Tel.: +32 2 4774856; fax: +32 2 4774855
    • ,
  • Ken Kersemans

      Affiliations

    • Radiopharmaceutical Chemistry (BEFY), Faculty of Medicine and Pharmacy, Vrije Universiteit Brussel, Laarbeeklaan 103, 1090 Brussels, Belgium
    • ,
  • Paul Geerlings

      Affiliations

    • General Chemistry (ALGC), Faculty of Sciences, Vrije Universiteit Brussel, Pleinlaan 2, 1050 Brussels, Belgium

Received 2 June 2008 ,Revised 13 June 2008 ,Accepted 19 June 2008.

References 

  1. Alberto R, Ortner K, Wheatly N, Schibli R, Schubiger AP. Synthesis and properties of borocarbonate/a convenient in situ CO source for the aqueous preparation of [99mTc(H2O)3(CO)3]+. J Am Chem Soc. 2001;123:3135–3136
  2. Schibli R, Schwazbach R, Ortner K, Schwalle H, Dumas C, Alberto R, et al. Steps toward high specific activity labeling of biomolecules for therapeutic applications: preparation of precursor [188Re(H2O)3(CO)3]+and synthesis tailor-made bifunctional ligand systems. Bioconjug Chem. 2002;13:750–756
  3. Schibli R, Schubiger PA. Current use and future potential of organometallic radiopharmaceuticals. Review article. Eur J Nucl Med. 2002;29:1529–1542
  4. Alberto R. New organometallic technetium complexes for radiopharmaceutical imaging. Top Curr Chem. 2005;252:1–44
  5. Alberto R, Schibli R, Waibel R, Abram U, Schubiger PA. Basic aqueous chemistry of [M(OH2)3(CO)3]+ (M=Re, Tc) directed towards radiopharmaceutical application. Coord Chem Rev 1999;190-192:901-19.
  6. Liu Y, Pak JK, Schmutz P, Bauwens M, Mertens J, Knight H, et al. Amino acids labeled with [99mTc(CO)3]+ and recognized by the L-type amino acid transporter LAT1. J Am Chem Soc. 2006;128:15996–15997
  7. Waibel R, Treichler H, Schaefer NG, van Staveren DR, Mundweiler S, Kunze S, et al. New derivatives of vitamin B12 show preferential targeting of tumours. Cancer Res. 2008;68:2904–2911
  8. Kunze S, Zobi F, Kurz P, Springler B, Alberto R. Vitamin B12 as ligand for technetium and rhenium complexes. Angew Chem Int Ed. 2004;43:5025
  9. Alberto R. The facettes of [99mTcCl3(CO)3]2 — Chemistry and its application to life sciences. J Nucl Radiochem Sci. 2005;6(3):173–176
  10. Knight H, Alberto R, Vries E, Kunze S, Mundwiler S. A novel technetium tricarbonyl complex of vitamin B12. J Labelled Comp Radiopharm. 2005;48:S34
  11. Szabo A, Ostlund NS. Modern Quantum Chemistry. New York: MacMillan; 1989;
  12. Davidson ER. Computational transition metal chemistry. Thematic Issue. Chem Rev. 2000;100(2):751–818
  13. Parr RG, Yang W. Density Functional Theory of Atoms and Molecules. New York: Oxford University Press; 1989;
  14. Koch W, Holthausen WMC. A Chemist's Guide to Density Functional Theory. Wiley-VCH: Weinheim; 2000;
  15. Parr RG, Yang W. Density-functional theory of the electronic structure of molecules. Annu Rev Phys Chem. 1995;46:701
  16. Chermette H. Chemical reactivity indexes in density functional theory. J Comput Chem. 1999;20:129
  17. Geerlings P, De Proft F, Langenaeker W. Conceptual density functional theory. Chem Rev. 2003;103:1793–1873
  18. De Proft F, Geerlings P. Conceptual and computational DFT in the study of aromaticity. Chem Rev. 2001;101:1451–1464
  19. Gancheff J, Kremer C, Kremer E, Ventura ON. Density functional study of technetium and rhenium compounds. J Mol Struct (Theochem). 2002;580:107–116
  20. Safi B, Mertens J, De Proft F, Alberto R, Geerlings P. Relative stability of mixed [3+1] Tc and Re complexes: a computational and conceptional DFT study. J Phys Chem. 2005;A109:1944
  21. Safi B, Mertens J, De Proft F, Geerlings P. A computational and conceptional density functional theory study of properties of Re and Tc tricarbonyl complexes. J Phys Chem. 2006;A110:9240
  22. Pearson RG. Hard and soft acids and bases. J Am Chem Soc. 1963;85:3533–3539
  23. Parr RG, Pearson RG. Absolute hardness: companion parameter to absolute electronegativity. J Am Chem Soc. 1983;105:7512–7516
  24. Gazquez JL, Mendez F. The hard and soft acids and bases principle: an atom in molecules viewpoint. J Phys Chem. 1994;98:4591–4593
  25. Geerlings P, De Proft F. HSAB principle: applications of its global and local forms in organic chemistry. Int J Quant Chem. 2000;80:227–235
  26. Becke AD. Density functional exchange energy approximation with correct asymptotic behavior. Phys Rev A. 1988;38:3098–3100
  27. Lee C, Yang W, Parr RG. Development of the Cole Salvetti correlation energy formula into a functional of the electron density. Phys Rev B. 1988;37:785–789
  28. Hehre WJ, Radom L, Schleyer PVR, Pople JA. Ab Initio Molecular Orbital Theory. New York: Wiley; 1986;
  29. Dunning TH. Gaussian basis sets for use in correlated molecular calculations: I. The atoms boron through neon and hydrogen. J Chem Phys. 1989;90(2):1007–1023
  30. Frisch MJ, Trucks GW, Schlegel HB, Gill PMW, Johnson BG, Robb MA, et al. Gaussian 98. Revision. A. 1. Pittsburgh PA: Gaussian, Inc.; 1998;
  31. Leibnitz P, Reck G, Pietzsch H-J, Spies H. Structure of technetium and rhenium complexes. Scientific-Technical Report. 2001;311:FZR
  32. Wang XY, Wang Y, Liu XQ, Chu TW, Hu SN, Wei XH, et al. The structure, energy and stability of components formed in the preparation of fac-[99m Tc (CO)3(H2O)3]+. Phys Chem Chem Phys. 2003;5:456–460
  33. Salignac B, Grundler PV, Cayemittes S, Frey U, Scopelliti R, Merbach AE. Reactivity of the organometallic fac-[(CO)3Re(I)(H2O)3]+ aquation. Kinetic and thermodynamic properties of H2O substitution. Inorg Chem. 2003;42:3516–3526
  34. Bonaccorsi R, Scrocco E, Tomasi J. Molecular SCF calculations for ground states: some three-membered ring molecules. J Chem Phys. 1970;52:5270–5284
  35. Chattaraj PK, Roy DR, Geerlings P, Torrent-Sucarrat M. Local hardness: a critical account. Theoret Chem Acc. 2007;118:923–930
  36. Kromer L, Spingler B, Alberto R. Synthesis and reactivity of ReBr2(NCCH3)2(CO)2]: a new precursor for bioorganometallic chemistry. J Organomet Chem. 2007;692:1372–1376
  37. Chen X, Guo Y, Liu B. Caution to HPLC analysis of tricarbonyl technetium radiopharmaceuticals: an example of changing constitution of complexes in column. J Pharm Biomed Anal. 2007;43:1576–1579
  38. Lakowicz JR, Castellano FN, Gryczynski I. Two-photon excitation of rhenium metal–ligand complexes. J Photochem Photobiol, A. 1999;122:95–101
  39. de Jong M, Bakker WH, Krenning EP, Breeman WAP, van der Pluijm ME, Bernard BF, et al. 90Y and 111In labeling, receptor binding and biodistribution of [DOTA, d-Phe,Tyr]octrotide, a promising somatostatin analogue for radionuclide therapy. Eur J Nucl Med. 1997;24:368–371
  40. Bakker WH, Albert R, Bruns C, Breeman WAP, Marbach LJ, Pless J, et al. [111In-DTPA-d-Phe]octrotide, a potential radiopharmaceutical for imaging of somatostatin receptor positive tumors: synthesis, radiolabeling and in vitro validation. Life Sci. 1991;49:1583–1591
  41. Alberto R, van Staveren DR, Benny PD, Kurz P, Pak JK. S-Functionalized cysteine: powerful ligands for the labeling of bioactive molecules with triaquatricarbonyltechnetium-99m(1+). Helv Chim Acta. 2005;88:447–460

PII: S0969-8051(08)00142-X

doi: 10.1016/j.nucmedbio.2008.06.003

Nuclear Medicine and Biology
Volume 35, Issue 7 , Pages 747-753 , October 2008

Article Tools

* Image Usage & Resolution