Technetium labeling of bi, tri and tetradentate ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid: Characterization and biodistribution of their oxo and nitrido 99mtechnetium complexes

We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN 2−, SNO 2−, SNN 2−, SNNO 3− and SNNN 3−) and different substituents on the sulfur moieties -SR (with R = H, CH 3 or C 2H 5O(CH 3)CH). With five of these ligands...

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Published inNuclear medicine and biology Vol. 23; no. 3; pp. 353 - 357
Main Authors Belhadj-Tahar, H., Coulais, Y., Cros, G., Darbieu, M.H., Tafani, J.A.M., Fabre, J., Esquerré, J.P., Guiraud, R.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier Inc 01.04.1996
Elsevier
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Abstract We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN 2−, SNO 2−, SNN 2−, SNNO 3− and SNNN 3−) and different substituents on the sulfur moieties -SR (with R = H, CH 3 or C 2H 5O(CH 3)CH). With five of these ligands technetium nitrido complexes have been obtained with high yields (over 95%) using rather harsh conditions (pH ≈ 1, temperature ≥ 80 °C), whereas for technetium oxo complexes similar high yields were only obtained with two ligands but with mild conditions (pH = 7–8, temperature ≈ 50 °C). Changing an OH group for an NH 2 has a drastic effect upon labeling yields. The possibility of complexing ligands as either oxo (TcO) 3+ or nitrido (TcN) 2+ derivatives increases the number of available labeled agents with different overall change and consequently with different biological behavior.
AbstractList We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN 2−, SNO 2−, SNN 2−, SNNO 3− and SNNN 3−) and different substituents on the sulfur moieties -SR (with R = H, CH 3 or C 2H 5O(CH 3)CH). With five of these ligands technetium nitrido complexes have been obtained with high yields (over 95%) using rather harsh conditions (pH ≈ 1, temperature ≥ 80 °C), whereas for technetium oxo complexes similar high yields were only obtained with two ligands but with mild conditions (pH = 7–8, temperature ≈ 50 °C). Changing an OH group for an NH 2 has a drastic effect upon labeling yields. The possibility of complexing ligands as either oxo (TcO) 3+ or nitrido (TcN) 2+ derivatives increases the number of available labeled agents with different overall change and consequently with different biological behavior.
We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN2-, SNO2-, SNN2-, SNNO3- and SNNN3-) and different substituents on the sulfur moieties-SR (with R = H, CH3 or C2H5O(CH3)CH). With five of these ligands technetium nitrido complexes have been obtained with high yields (over 95%) using rather harsh conditions (pH = 1, temperature > or = 80 degrees C), whereas for technetium oxo complexes similar high yields were only obtained with two ligands but with mild conditions (pH = 7-8, temperature approximately equal to 50 degrees C). Changing an OH group for an NH2 has a drastic effect upon labeling yields. The possibility of complexing ligands as either oxo (TcO)3+ or nitrido (TcN)2+ derivatives increases the number of available labeled agents with different overall change and consequently with different biological behavior.
We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN2-, SNO2-, SNN2-, SNNO3- and SNNN3-) and different substituents on the sulfur moieties-SR (with R = H, CH3 or C2H5O(CH3)CH). With five of these ligands technetium nitrido complexes have been obtained with high yields (over 95%) using rather harsh conditions (pH = 1, temperature > or = 80 degrees C), whereas for technetium oxo complexes similar high yields were only obtained with two ligands but with mild conditions (pH = 7-8, temperature approximately equal to 50 degrees C). Changing an OH group for an NH2 has a drastic effect upon labeling yields. The possibility of complexing ligands as either oxo (TcO)3+ or nitrido (TcN)2+ derivatives increases the number of available labeled agents with different overall change and consequently with different biological behavior.
Author Fabre, J.
Belhadj-Tahar, H.
Cros, G.
Guiraud, R.
Darbieu, M.H.
Tafani, J.A.M.
Coulais, Y.
Esquerré, J.P.
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  organization: Laboratoire d'Imagerie Morphologique et Fonctionnelle, EA 826, Faculté de Médecine Toulouse-Purpan, 133 Route de Narbonne, 31062 Toulouse Cedex, France
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Cites_doi 10.1016/0883-2889(91)90190-C
10.1016/0969-8051(94)90018-3
10.1016/0020-1693(94)04127-X
10.1021/ic50187a005
10.1016/0883-2889(89)90102-0
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10.1021/jm00122a024
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10.1007/BF00935932
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Issue 3
Keywords Nitridotechnetium
2-Aminocyclopentene-1-dithiocarboxylic acid
Aminothiol
Complexes
Biodistribution
Technetium-99m
Radiolabelling
Dithiocarboxylic acid
Ligand
Radiochemistry
Technetium
Bioavailability
Experimental study
Pharmacokinetics
Chemical synthesis
Chromatography
Comparative study
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Elsevier
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Snippet We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN 2−, SNO 2−, SNN 2−,...
We have synthesized and characterized seven ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid with different donor sets (SN2-, SNO2-, SNN2-,...
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SubjectTerms 2-Aminocyclopentene-1-dithiocarboxylic acid
Aminothiol
Animals
Biodistribution
Biological and medical sciences
Complexes
Contrast media. Radiopharmaceuticals
Isotope Labeling - methods
Ligands
Magnetic Resonance Spectroscopy
Male
Medical sciences
Molecular Structure
Nitridotechnetium
Pharmacology. Drug treatments
Rats
Rats, Wistar
Structure-Activity Relationship
Technetium - pharmacokinetics
Technetium-99m
Thiones - chemical synthesis
Thiones - chemistry
Thiones - pharmacokinetics
Tissue Distribution
X-Ray Diffraction
Title Technetium labeling of bi, tri and tetradentate ligands derived from 2-aminocyclopentene-1-dithiocarboxylic acid: Characterization and biodistribution of their oxo and nitrido 99mtechnetium complexes
URI https://dx.doi.org/10.1016/0969-8051(95)02100-0
https://www.ncbi.nlm.nih.gov/pubmed/8782247
https://search.proquest.com/docview/78288025
Volume 23
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