Functionalized rhenium(V) organoimido complexes as potential radiopharmaceuticals.: 2.: Synthesis, structural characterization, and reactivity of N-succinimidyl ester derivatives with amines

被引:31
作者
Arterburn, JB
Rao, KV
Goreham, DM
Valenzuela, MV
Holguin, MS
Hall, KA
Ott, KC
Bryan, JC
机构
[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA
[2] Los Alamos Natl Lab, CST Div, Los Alamos, NM 87545 USA
[3] Glaxo Wellcome Res & Dev Ltd, Med Res Ctr, Stevenage SG1 2NY, Herts, England
[4] Symyx Technol Inc, Santa Clara, CA 95051 USA
[5] Oak Ridge Natl Lab, Div Chem & Analyt Sci, Oak Ridge, TN 37831 USA
关键词
D O I
10.1021/om990929w
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Organoimidorhenium(V) complexes were synthesized as potential labeling agents for biologically relevant organic amines using the preconjugate approach. The bistriphenylphosphine organoimidorhenium N-succinimidyl ester complex Cl-3(PPh3)(2)Re=N-C6H4CO2N-(COCH2)(2) (2) was synthesized and characterized by single-crystal X-ray analysis. Complex 2 was coupled in aqueous dimethylformamide solvent with a series of primary and secondary amines, aminoacids, and a biotin-ethylenediamine derivative to give the corresponding amide complexes in good yields. These results demonstrate that the organoimido linkage is resistant toward hydrolysis and stable in the presence of more basic alkylamines. An unusual oxygen atom transfer reaction was observed between the byproduct N-hydroxysuccinimide and triphenylphosphine ligands when dichloromethane was used as solvent. The dithiocarbamate complexes Cl[Et2NCS2](2)Re=N-C6H4CO2N(COCH2)(2) (3) and O[(Et2NCS2)(2)Re=N-C6H4-CO2N(COCH2)(2)](2) (4) were also synthesized from 2. These complexes were unaffected by N-hydroxysuccinimide, but were not suitable for labeling due to hydrolysis of the organoimido groups under the reaction conditions.
引用
收藏
页码:1789 / 1795
页数:7
相关论文
共 54 条