A new synthesis of TE2A-a potential bifunctional chelator for 64Cu

Nuclear Medicine and Molecular Imaging

Volumn 44, Issue 3, 2010, Pages 185-192

  Pandya, Darpan N ^a   Kim, Jung Young ^b   Kwak, Wonjung ^a   Park, Jeong Chan ^a   Gawande, Manoj B ^a   An, Gwang Il ^b   Ryu, Eun Kyoung ^c   Yoo, Jeongsoo ^a  

^a Kyungpook National University School of Medicine   (South Korea)

^b Korea Institute of Radiation and Medical Science   (South Korea)

^c Korea Basic Science Institute (KBSI)   (South Korea)

Author keywords

64Cu; Bifunctional chelator; Conjugation; RGD peptide; TE2A

Indexed keywords

1,8 N,N' BIS (CARBOXYMETHYL) 1,4,8,11 TETRAAZACYCLOTETRADECANE; ARGINYLGLYCYLASPARTIC ACID; CHELATING AGENT; COPPER 64; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONJUGATION; CONTROLLED STUDY; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; REACTION OPTIMIZATION;

EID: 79952735237     PISSN: 18693474     EISSN: 18693482     Source Type: Journal    
DOI: 10.1007/s13139-010-0031-2     Document Type: Article

References (35)

1. Wainwright KP. (1997) Synthetic and structural aspects of the chemistry of saturated polyaza macrocyclic ligands bearing pendant coordinating groups attached to nitrogen. Coord Chem Rev 166:35-90.
2. Alexander V. (1995) Design and synthesis of macrocyclic ligands and their complexes of lanthanides and actinides. Chem Rev 95 (2):273-342.
3. Kimura E. (1992) Macrocyclic polyamines with intelligent functions. Tetrahedron 48(30):6175-217.
4. Izatt RM, Pawlak K, Bradshaw JS, Bruening RL. (1995) Thermodynamic and kinetic data for macrocycle interaction with cations, anions, and neutral molecules. Chem Rev 95(7):2529-86.
5. Bolm C, Meyer N, Raabe G, Weyhermuller T, Bothe E. (2000) A novel enantiopure proline-derived triazacyclononane: synthesis, structure and application of its manganese complex. Chem Commun 24:2435-6.
6. Breslow R, Berger D, Huang DL. (1990) Bifunctional zincimidazole and zinc-thiophenol catalysts. J Am Chem Soc 112 (9), 3686-7.
7. 2 reduction. Inorg Chem 35(18):5132-6.
8. Wieghardt K. (1989) The active sites in manganese-containing metalloproteins and inorganic model complexes. Angew Chem Int Ed Engl 28:1153-72.
9. Chapman WH Jr, Breslow R. (1995) Selective hydrolysis of phosphate esters, nitrophenyl phosphates and UpU, by dimeric zinc complexes depends on the spacer length. J Am Chem Soc 117(20):5462-9.
10. Rossi P, Felluga F, Tecilla P, Formaggio F, CrismaM, Toniolo C et al. (1999) A bimetallic helical heptapeptide as a transphosphorylation catalyst in water. J Am Chem Soc 121(29):6948-9.
11. Sissi C, Rossi P, Felluga F, Formaggio F, Palumbo M, Tecilla P et al. (2001) Dinuclear Zn2+ complexes of synthetic heptapeptides as artificial nucleases. J Am Chem Soc 123(13):3169-70.
12. Young MJ, Chin J. (1995) Dinuclear copper(II) complex that hydrolyzes RNA. J Am Chem Soc 117(42):10577-8.
13. Li C, Wong W-T. (2002) Luminescent terbium(III) complexes with pendant crown ethers responding to alkali metal ions and aromatic antennae in aqueous solution. Chem Commun 18:2034-5.
14. Caravan P, Ellison JJ, McMurry TJ, Lauffer RB. (1999) Gadolinium (III) chelates as MRI contrast agents: structure, dynamic, and applications. Chem Rev 99:2293-352.
15. Reichert DE, Lewis J, Anderson CJ. (1999) Metal complexes as diagnostic tools. Coord Chem Rev 184:3-66.
16. Nayak TK, Brechbiel MW. (2009) Radioimmunoimaging with longer-lived positron-emitting radionuclides: potentials and challenges. Bioconjug Chem 20(5):825-41.
17. Liu S. (2008) Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides. Adv Drug Deliv Rev 60(12):1347-70.
18. Chappell LL, Dadachova E, Milenic DE, Garmestani K, Wu C, Brechbiel MW. (2000) Synthesis, characterization, and evaluation of a novel bifunctional chelating agent for the lead isotopes 203Pb and 212Pb. Nucl Med Biol 27(1):93-100.
19. Chan KW-Y, Wong W-T. (2007) Small molecular gadolinium(III) complexes as MRI contrast agents for diagnostic imaging. Coord Chem Rev 251(17-20):2428-51.
20. Shokeen M, Anderson CJ. (2009) Molecular imaging of cancer with copper-64 radiopharmaceuticals and positron emission tomography (PET). Acc Chem Res 42(7):832-41.
21. De Leon-Rodriguez LM, Kovacs Z. (2008) The synthesis and chelation chemistry of DOTA-peptide conjugates. Bioconjug Chem 19(2):391-402.
22. Liu S, Edwards DS. (2001) Bifunctional chelators for therapeutic lanthanide radiopharmaceuticals. Bioconjug Chem 12(1):7-34.
23. Delgado R, Felix V, Lima LMP, Price DW. (2007) Metal complexes of cyclen and cyclam derivatives useful for medical applications: a discussion based on thermodynamic stability constants and structural data. Dalton Trans 26:2734-45.
24. Chang CA, Liu Y-L, Chen C-Y, Chou X-M. (2001) Ligand preorganization in metal ion complexation: molecular mechanics/dynamics, kinetics, and laser-excited luminescence studies of trivalent lanthanide complex formation with macrocyclic ligands TETA and DOTA. Inorg Chem 40(14):3448-55.
25. Pandya DN, Kim JY, Park JC, Lee H, Phapale PB, Kwak W et al. (2010) Revival of TE2A; a better chelate for Cu(II) ions than TETA? Chem Commun 46:3517-9.
26. Royal G, Dihaoui-Gindrey V, Dahaoui S, Tabard A, Guilard R, Pullumbi P et al. (1998) New synthesis of trans-disubstituted cyclam macrocycles. Elucidation of the disubstitution mechanism on the basis of x-ray data and molecular modeling. Eur J Org Chem 9:1971-5.
27. 5,8]tetradecane. J Chem Soc Chem Commun 16:1094-5.
28. Helps IM, Parker D, Morphy JR, Chapman J. (1989) General routes for the synthesis of mono, di and tri-N-substituted derivatives of cyclam. Tetrahedron 45(1):219-26.
29. Chapman J, Ferguson G, Gallagher JF, Jennings MC, Parker D. (1992) Copper and nickel complexes of 1,8-disubstituted derivatives of 1,4,8,11-tetraazacyclotetradecane. J Chem Soc Dalton Trans 3:345-53.
30. Kovacs Z, Sherry AD. (1995) A general synthesis of 1, 7-disubstituted 1, 4, 7, 10-tetraazacyclododecanes. J Chem Soc Chem Commun 2:185-6.
31. Liu S. (2009) Radiolabeled cyclic RGD peptides as integrin alpha (v)beta(3)-targeted radiotracers: maximizing binding affinity via bivalency. Bioconjug Chem 20(12):2199-213.
32. Luppi G, Garelli A, Prodi L, Broxterman QB, Kaptein B, Tomasini C. (2005) Development of new calcium receptors based on oxazolidin-2-ones containing pseudopeptides. Org Biomol Chem 3(8):1520-4.
33. Wong EH, Weisman GR, Hill DC, Reed DP, Rogers ME, Condon JS et al. (2000) Synthesis and characterization of cross-bridged cyclams and pendant-armed derivatives and structural studies of their copper(II) complexes. J Am Chem Soc 122:10561-72.
34. Sprague JE, Peng Y, Fiamengo AL, Woodin KS, Southwick EA, Weisman GR et al. (2007) Synthesis, characterization and in vivo studies of Cu(II)-64-labeled cross-bridged tetraazamacrocycleamide complexes as models of peptide conjugate imaging agents. J Med Chem 50(10):2527-35.
35. Sprague JE, Peng Y, Sun X, Weisman GR, Wong EH, Achilefu S et al. (2004) Preparation and biological evaluation of copper-64-labeled Tyr3-octreotate using a cross-bridged macrocyclic chelator. Clin Cancer Res 10(24):8674-82.