Document Detail


Synthesis and evaluation of a radiometal-labeled macrocyclic chelator-derivatised thymidine analog.
MedLine Citation:
PMID:  16631084     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Several radiolabeled thymidine analogs as metabolic probes of cell proliferation were developed specifically addressing DNA synthesis. Thymidine analogs containing carboranylalkyl groups for neutron capture therapy at the N-3 position were found to be good substrates for cytosolic thymidine kinase 1 (TK1). According to this approach, a DO3A macrocycle in N-3 position was attached to thymidine. The 3-DO3A thymidine analog was labeled with 68Ga and 111In. Different lipophilicities of the corresponding radiometal-thymidines were detected via RP-HPLC. [111In]DO3A-thymidine ([111In]D3T) was evaluated for cellular uptake in different cell lines (HL60 and DoHH2). Cellular uptake was low in both cell lines. Phosphorylation of the radioconjugates by TK1 was negligible. Although stable complexation of radiometals to thymidine was obtained, introduction of the macrocycle DO3A reduced the affinity to cytosolic TK1 drastically. Low cellular uptake can be ascribed to missing substrate specificity of [111In]DO3A-thymidine for TK1. The absence of substrate specificity may be due to the bulky macrocyclic chelator and partial charges remaining on the coordination sphere due to a more complex solution structure.
Authors:
Michaela Schmid; Bernd Neumaier; Andreas T J Vogg; Katrin Wczasek; Claudia Friesen; Felix M Mottaghy; Andreas K Buck; Sven N Reske
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2006-03-09
Journal Detail:
Title:  Nuclear medicine and biology     Volume:  33     ISSN:  0969-8051     ISO Abbreviation:  Nucl. Med. Biol.     Publication Date:  2006 Apr 
Date Detail:
Created Date:  2006-04-24     Completed Date:  2006-12-18     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9304420     Medline TA:  Nucl Med Biol     Country:  England    
Other Details:
Languages:  eng     Pagination:  359-66     Citation Subset:  IM    
Affiliation:
Department of Nuclear Medicine, University Hospital Ulm, 89081 Ulm, Germany.
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MeSH Terms
Descriptor/Qualifier:
Chelating Agents / chemistry
Gallium Radioisotopes / pharmacokinetics*
HL-60 Cells / drug effects
Heterocyclic Compounds, 1-Ring / chemical synthesis*,  pharmacokinetics
Humans
Indium Radioisotopes / pharmacokinetics*
Ligands
Lymphoma, B-Cell / metabolism*
Phosphorylation
Substrate Specificity
Thymidine / chemical synthesis*,  pharmacokinetics*
Thymidine Kinase / metabolism
Tumor Cells, Cultured
Chemical
Reg. No./Substance:
0/1,4,7-tris(tert-butylacetate)-1,4,7,10-tetraazacyclododecane ester; 0/Chelating Agents; 0/Gallium Radioisotopes; 0/Heterocyclic Compounds, 1-Ring; 0/Indium Radioisotopes; 0/Ligands; 50-89-5/Thymidine; EC 2.7.1.21/Thymidine Kinase; EC 2.7.1.21/thymidine kinase 1

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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