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Synthesis of multidentate ligands with amido or amino donor groups for the preparation of rhenium and technetium radiopharmaceuticals.

Al-Nuzal SM, Al-Azzawi HM, Al-Mosawy ZM - J Radioanal Nucl Chem (2012)

Bottom Line: The method was based on formylation of substituted anilines, followed by Mannich reaction with glycine and paraformaldehyde.The complexes were prepared through ligand exchange with the complex ReOCl3(PPh3)2, giving new complex of the structure ReOCl3L(1-5).These ligands were labeled with (99m)Tc pertechnetate, and the labeling efficiency of the complexes was measured using a well type scintillation gamma counter equipment and obtained a good yield.

View Article: PubMed Central - PubMed

Affiliation: Environmental Research Centre, The University of Technology, Baghdad, Iraq.

ABSTRACT

A new method to prepare novel semi-rigid multidentate ligands containing nitrogen atom, to coordinate with rhenium and technetium, was established. The method was based on formylation of substituted anilines, followed by Mannich reaction with glycine and paraformaldehyde. The method was very promising to design ligands of various molecular structures (L1-L5) to coordinate with rhenium metal ions. The complexes were prepared through ligand exchange with the complex ReOCl3(PPh3)2, giving new complex of the structure ReOCl3L(1-5). The prepared ligands and complexes were identified by the use of UV-vis, and infrared absorption spectrometric techniques, elemental analysis, molecular weight determination by depression of freezing point. These ligands were labeled with (99m)Tc pertechnetate, and the labeling efficiency of the complexes was measured using a well type scintillation gamma counter equipment and obtained a good yield.

No MeSH data available.


Related in: MedlinePlus

The UV–visible spectrum of phenylene diamine (dashed line), N,N′-diformyl phenylene diamine (dot-dashed line), and Bis-N,N′(Glycylacetyl) phenylene diamine (continuous line)
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Fig4: The UV–visible spectrum of phenylene diamine (dashed line), N,N′-diformyl phenylene diamine (dot-dashed line), and Bis-N,N′(Glycylacetyl) phenylene diamine (continuous line)

Mentions: The formyl derivatives and Mannich reaction substituted anilines were prepared following the general procedures mentioned in the experimental part. They were obtained in good purity and radiolabeling yields (~70 % in general). Their physical, UV–visible, and IR absorption spectroscopic properties of the formyl derivatives (I–V) and their Mannich reaction products with glycine (L1–L5) as well as the 1:1 coordination products ReOCl3L (C1–C5), were presented in Tables 1, 2, and 3. The proposed chemical structure of the Mannich reaction products were presented in Fig. 1. These results were in good agreement with the proposed chemical structure of the products. All formyl derivatives showed two new absorption bands at 1,668–1,735 and at 2850–2750 cm−1 in the FT-IR spectra corresponding the attachment of formyl group on anilines. The first one was due to the C=O stretching, while the second one was due to the C–H aliphatic stretching. The second absorption band disappeared upon Mannich reaction substitution. λmax of the UV–visible absorption spectra of the substituted anilines used as starting materials showed clear shift to higher wave length upon substitution with the formyl group, and with methyl glycine after Mannich reaction. Generally, this shift is accompanied with increase in the value of λmax of the products due to the hyperconjugation of the amine proton with benzene ring (Figs. 2, 3, 4). This new method will offer reliable procedure to design ligands of the following general structure.Table 1


Synthesis of multidentate ligands with amido or amino donor groups for the preparation of rhenium and technetium radiopharmaceuticals.

Al-Nuzal SM, Al-Azzawi HM, Al-Mosawy ZM - J Radioanal Nucl Chem (2012)

The UV–visible spectrum of phenylene diamine (dashed line), N,N′-diformyl phenylene diamine (dot-dashed line), and Bis-N,N′(Glycylacetyl) phenylene diamine (continuous line)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4514609&req=5

Fig4: The UV–visible spectrum of phenylene diamine (dashed line), N,N′-diformyl phenylene diamine (dot-dashed line), and Bis-N,N′(Glycylacetyl) phenylene diamine (continuous line)
Mentions: The formyl derivatives and Mannich reaction substituted anilines were prepared following the general procedures mentioned in the experimental part. They were obtained in good purity and radiolabeling yields (~70 % in general). Their physical, UV–visible, and IR absorption spectroscopic properties of the formyl derivatives (I–V) and their Mannich reaction products with glycine (L1–L5) as well as the 1:1 coordination products ReOCl3L (C1–C5), were presented in Tables 1, 2, and 3. The proposed chemical structure of the Mannich reaction products were presented in Fig. 1. These results were in good agreement with the proposed chemical structure of the products. All formyl derivatives showed two new absorption bands at 1,668–1,735 and at 2850–2750 cm−1 in the FT-IR spectra corresponding the attachment of formyl group on anilines. The first one was due to the C=O stretching, while the second one was due to the C–H aliphatic stretching. The second absorption band disappeared upon Mannich reaction substitution. λmax of the UV–visible absorption spectra of the substituted anilines used as starting materials showed clear shift to higher wave length upon substitution with the formyl group, and with methyl glycine after Mannich reaction. Generally, this shift is accompanied with increase in the value of λmax of the products due to the hyperconjugation of the amine proton with benzene ring (Figs. 2, 3, 4). This new method will offer reliable procedure to design ligands of the following general structure.Table 1

Bottom Line: The method was based on formylation of substituted anilines, followed by Mannich reaction with glycine and paraformaldehyde.The complexes were prepared through ligand exchange with the complex ReOCl3(PPh3)2, giving new complex of the structure ReOCl3L(1-5).These ligands were labeled with (99m)Tc pertechnetate, and the labeling efficiency of the complexes was measured using a well type scintillation gamma counter equipment and obtained a good yield.

View Article: PubMed Central - PubMed

Affiliation: Environmental Research Centre, The University of Technology, Baghdad, Iraq.

ABSTRACT

A new method to prepare novel semi-rigid multidentate ligands containing nitrogen atom, to coordinate with rhenium and technetium, was established. The method was based on formylation of substituted anilines, followed by Mannich reaction with glycine and paraformaldehyde. The method was very promising to design ligands of various molecular structures (L1-L5) to coordinate with rhenium metal ions. The complexes were prepared through ligand exchange with the complex ReOCl3(PPh3)2, giving new complex of the structure ReOCl3L(1-5). The prepared ligands and complexes were identified by the use of UV-vis, and infrared absorption spectrometric techniques, elemental analysis, molecular weight determination by depression of freezing point. These ligands were labeled with (99m)Tc pertechnetate, and the labeling efficiency of the complexes was measured using a well type scintillation gamma counter equipment and obtained a good yield.

No MeSH data available.


Related in: MedlinePlus