Literature DB >> 19101152

A novel side-bridged hybrid phosphonate/acetate pendant cyclam: synthesis, characterization, and 64Cu small animal PET imaging.

C Andrew Boswell1, Celeste A S Regino, Kwamena E Baidoo, Karen J Wong, Diane E Milenic, James A Kelley, Christopher C Lai, Martin W Brechbiel.   

Abstract

Copper-64 (t(1/2)=12.7h; n>an class="Chemical">beta(+): 0.653 MeV, 17.4%; beta(-): 0.578 MeV, 39%) is produced in a biomedical cyclotron and has applications in both imaging and therapy. Macrocyclic chelators are widely used as bifunctional chelators to bind copper radionuclides to antibodies and peptides owing to their relatively high kinetic stability. A novel side-bridged cyclam featuring both pendant acetate and phosphonate groups was synthesized using a Kabachnik-Fields approach followed by hydrobromic acid deprotection. The Cu(II) complex of the novel ligand was synthesized, radiolabeling with (64)Cu was demonstrated, and in vitro (serum) stability was performed. In addition, in vivo distribution and clearance of the (64)Cu-labeled complex was visualized by positron emission tomography (PET) imaging. This novel chelate may be useful in (64)Cu-mediated diagnostic positron emission tomography (PET) imaging as well as targeted radiotherapeutic applications.

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Year:  2008        PMID: 19101152      PMCID: PMC2636550          DOI: 10.1016/j.bmc.2008.11.073

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN: 0968-0896            Impact factor:   3.641


  24 in total

1.  Synthesis and NMR studies of new DOTP-like lanthanide(III) complexes containing a hydrophobic substituent on one phosphonate side arm.

Authors:  X Li; S Zhang; P Zhao; Z Kovacs; A D Sherry
Journal:  Inorg Chem       Date:  2001-12-17       Impact factor: 5.165

2.  Stability and Structure of Activated Macrocycles. Ligands with Biological Applications.

Authors:  Ramunas J. Motekaitis; Buck E. Rogers; David E. Reichert; Arthur E. Martell; Michael J. Welch
Journal:  Inorg Chem       Date:  1996-06-19       Impact factor: 5.165

3.  Transfer of copper from a chelated 67Cu-antibody conjugate to ceruloplasmin in lymphoma patients.

Authors:  G R Mirick; R T O'Donnell; S J DeNardo; S Shen; C F Meares; G L DeNardo
Journal:  Nucl Med Biol       Date:  1999-10       Impact factor: 2.408

4.  Cyclam (1,4,8,11-tetraazacyclotetradecane) with one methylphosphonate pendant arm: a new ligand for selective copper(ii) binding.

Authors:  Silvia Füzerová; Jan Kotek; Ivana Císarová; Petr Hermann; Koen Binnemans; Ivan Lukes
Journal:  Dalton Trans       Date:  2005-07-26       Impact factor: 4.390

5.  64Cu-TETA-octreotide as a PET imaging agent for patients with neuroendocrine tumors.

Authors:  C J Anderson; F Dehdashti; P D Cutler; S W Schwarz; R Laforest; L A Bass; J S Lewis; D W McCarthy
Journal:  J Nucl Med       Date:  2001-02       Impact factor: 10.057

6.  67Cu-versus 131I-labeled Lym-1 antibody: comparative pharmacokinetics and dosimetry in patients with non-Hodgkin's lymphoma.

Authors:  G L DeNardo; D L Kukis; S Shen; D A DeNardo; C F Meares; S J DeNardo
Journal:  Clin Cancer Res       Date:  1999-03       Impact factor: 12.531

7.  Optimization of labeling and metabolite analysis of copper-64-labeled azamacrocyclic chelators by radio-LC-MS.

Authors:  C Andrew Boswell; Paul McQuade; Gary R Weisman; Edward H Wong; Carolyn J Anderson
Journal:  Nucl Med Biol       Date:  2005-01       Impact factor: 2.408

8.  Comparison of four bifunctional chelates for radiolabeling monoclonal antibodies with copper radioisotopes: biodistribution and metabolism.

Authors:  B E Rogers; C J Anderson; J M Connett; L W Guo; W B Edwards; E L Sherman; K R Zinn; M J Welch
Journal:  Bioconjug Chem       Date:  1996 Jul-Aug       Impact factor: 4.774

9.  Copper-67-labeled monoclonal antibody Lym-1, a potential radiopharmaceutical for cancer therapy: labeling and biodistribution in RAJI tumored mice.

Authors:  S V Deshpande; S J DeNardo; C F Meares; M J McCall; G P Adams; M K Moi; G L DeNardo
Journal:  J Nucl Med       Date:  1988-02       Impact factor: 10.057

10.  High thermodynamic stability and extraordinary kinetic inertness of copper(II) complexes with 1,4,8,11-tetraazacyclotetradecane-1,8-bis(methylphosphonic acid): example of a rare isomerism between kinetically inert penta- and hexacoordinated copper(II) complexes.

Authors:  Jan Kotek; Premysl Lubal; Petr Hermann; Ivana Císarová; Ivan Lukes; Tomás Godula; Ivona Svobodová; Petr Táborský; Josef Havel
Journal:  Chemistry       Date:  2003-01-03       Impact factor: 5.236

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  7 in total

Review 1.  Coordinating radiometals of copper, gallium, indium, yttrium, and zirconium for PET and SPECT imaging of disease.

Authors:  Thaddeus J Wadas; Edward H Wong; Gary R Weisman; Carolyn J Anderson
Journal:  Chem Rev       Date:  2010-05-12       Impact factor: 60.622

2.  Synthesis, structural studies, and oxidation catalysis of the manganese(II), iron(II), and copper(II) complexes of a 2-pyridylmethyl pendant armed side-bridged cyclam.

Authors:  Anthony D Shircliff; Kevin R Wilson; Desiray J Cannon; Donald G Jones; Zhan Zhang; Zhuqi Chen; Guochuan Yin; Timothy J Prior; Timothy J Hubin
Journal:  Inorg Chem Commun       Date:  2015-09-01       Impact factor: 2.495

Review 3.  Diagnosis and therapy are walking together on radiopeptides' avenue.

Authors:  Luigi Mansi; Irene Virgolini
Journal:  Eur J Nucl Med Mol Imaging       Date:  2011-04       Impact factor: 9.236

4.  Monoclonal antibodies for copper-64 PET dosimetry and radioimmunotherapy.

Authors:  Jeffrey N Bryan; Fang Jia; Huma Mohsin; Geethapriya Sivaguru; Carolyn J Anderson; William H Miller; Carolyn J Henry; Michael R Lewis
Journal:  Cancer Biol Ther       Date:  2011-06-15       Impact factor: 4.742

5.  Synthesis, Cu(II) complexation, 64Cu-labeling and biological evaluation of cross-bridged cyclam chelators with phosphonate pendant arms.

Authors:  Riccardo Ferdani; Dannon J Stigers; Ashley L Fiamengo; Lihui Wei; Barbara T Y Li; James A Golen; Arnold L Rheingold; Gary R Weisman; Edward H Wong; Carolyn J Anderson
Journal:  Dalton Trans       Date:  2011-12-15       Impact factor: 4.390

6.  Copper-64 radiopharmaceuticals for PET imaging of cancer: advances in preclinical and clinical research.

Authors:  Carolyn J Anderson; Riccardo Ferdani
Journal:  Cancer Biother Radiopharm       Date:  2009-08       Impact factor: 3.099

7.  Cyclam-based polymeric copper chelators for gene delivery and potential PET imaging.

Authors:  Jing Li; Yu Zhu; Stuart T Hazeldine; Steven M Firestine; David Oupický
Journal:  Biomacromolecules       Date:  2012-09-25       Impact factor: 6.988

  7 in total

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