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

Abstract

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{sub 3}(PPh{sub 3}){sub 2}Re{double_bond}N-C{sub 6}H{sub 4}CO{sub 2}N-(COCH{sub 2}){sub 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, amino acids, 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[Et{sub 2}NCS{sub 2}]{sub 2}Re{double_bond}N-C{sub 6}H{sub 4}CO{sub 2}N(COCH{sub 2}){sub 2} (3) and o[(Et{sub 2}NCS{sub 2}){sub 2}Re{double_bond}N-C{sub 6}H{sub 4}-CO{sub 2}N(COCH{sub 2}){sub 2}]{sub 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.

Authors:
; ; ; ; ; ; ;
Publication Date:
Research Org.:
New Mexico State Univ., Las Cruces, NM (US)
OSTI Identifier:
20075590
Resource Type:
Journal Article
Journal Name:
Organometallics
Additional Journal Information:
Journal Volume: 19; Journal Issue: 9; Other Information: PBD: 1 May 2000; Journal ID: ISSN 0276-7333
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; RHENIUM COMPLEXES; ORGANIC NITROGEN COMPOUNDS; RADIOPHARMACEUTICALS; SYNTHESIS; MOLECULAR STRUCTURE

Citation Formats

Arterburn, J.B., Rao, K.V., Goreham, D.M., Valenzuela, M.V., Holguin, M.S., Hall, K.A., Ott, K.C., and Bryan, J.C. Functionalized rhenium(V) organoimido complexes as potential radiopharmaceuticals. 2. Synthesis, structural characterization, and reactivity of N-succinimidyl ester derivatives with amines. United States: N. p., 2000. Web. doi:10.1021/om990929w.
Arterburn, J.B., Rao, K.V., Goreham, D.M., Valenzuela, M.V., Holguin, M.S., Hall, K.A., Ott, K.C., & Bryan, J.C. Functionalized rhenium(V) organoimido complexes as potential radiopharmaceuticals. 2. Synthesis, structural characterization, and reactivity of N-succinimidyl ester derivatives with amines. United States. doi:10.1021/om990929w.
Arterburn, J.B., Rao, K.V., Goreham, D.M., Valenzuela, M.V., Holguin, M.S., Hall, K.A., Ott, K.C., and Bryan, J.C. Mon . "Functionalized rhenium(V) organoimido complexes as potential radiopharmaceuticals. 2. Synthesis, structural characterization, and reactivity of N-succinimidyl ester derivatives with amines". United States. doi:10.1021/om990929w.
@article{osti_20075590,
title = {Functionalized rhenium(V) organoimido complexes as potential radiopharmaceuticals. 2. Synthesis, structural characterization, and reactivity of N-succinimidyl ester derivatives with amines},
author = {Arterburn, J.B. and Rao, K.V. and Goreham, D.M. and Valenzuela, M.V. and Holguin, M.S. and Hall, K.A. and Ott, K.C. and Bryan, J.C.},
abstractNote = {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{sub 3}(PPh{sub 3}){sub 2}Re{double_bond}N-C{sub 6}H{sub 4}CO{sub 2}N-(COCH{sub 2}){sub 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, amino acids, 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[Et{sub 2}NCS{sub 2}]{sub 2}Re{double_bond}N-C{sub 6}H{sub 4}CO{sub 2}N(COCH{sub 2}){sub 2} (3) and o[(Et{sub 2}NCS{sub 2}){sub 2}Re{double_bond}N-C{sub 6}H{sub 4}-CO{sub 2}N(COCH{sub 2}){sub 2}]{sub 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.},
doi = {10.1021/om990929w},
journal = {Organometallics},
issn = {0276-7333},
number = 9,
volume = 19,
place = {United States},
year = {2000},
month = {5}
}