Document Type

Honors Capstone Project

Date of Submission

Spring 5-1-2014

Capstone Advisor

Dr. Jon A. Zubieta

Honors Reader

Kelly Henry

Capstone Major

Chemistry

Capstone College

Arts and Science

Audio/Visual Component

no

Capstone Prize Winner

no

Won Capstone Funding

no

Honors Categories

Sciences and Engineering

Subject Categories

Chemistry | Medicinal-Pharmaceutical Chemistry | Radiochemistry

Abstract

Nuclear imaging used in diagnostic medicine requires the use of radiopharmaceuticals to make biological areas visible under a gamma camera. Although much success has been found in the use of technetium based imaging agents, their corresponding rhenium complexes can provide insight into the chemical properties of these radiopharmaceuticals without the potentially damaging effects of radiation. Technetium and rhenium complexes utilize a bifunctional chelator to act as a linker between biological vectors and the metal, improving the coordination between the two. Ligands containing thiazole rings have been successfully coordinated to technetium or rhenium tricarbonyl complexes, although it is uncertain whether coordination occurs through the nitrogen or the sulfur of the thiazole ring. Imaging studies of isomers of these compounds have extended understanding of the functioning of these compounds by providing insight into the chemistry of their coordination.

This project involves the study of [Re(CO)3-1,1-bisthiazolate-(1,4)-diaminobutane] as a surrogate for the technetium based complex. The precursor to this complex, N1,N1-bis(thiazol-2, 4, or 5-ylmethyl)butane-1,4-diamine has been successfully synthesized using thiazole ring containing isomers, thiazole-2-carboxaldehyde, thiazole-4-carboxaldehyde, and thiazole-5-carboxaldehyde. Reverse-phase high performance liquid chromatography and characterization through 1H-Nuclear Magnetic Resonance (1H-NMR) and Electrospray Ionization-Mass Spectrometry (ESI-MS) have been completed to purify and confirm the presence of the desired products.

HPLC chromatograms for N1,N1-bis(thiazol-2,4, or 5-ylmethyl)butane-1,4-diamine synthesized with thiazole-2-carboxaldehyde, thiazole-4-carboxaldehyde, or thiazole-5-carboxaldehyde give singular peaks indicating significant ligand purity and relatively poor yield. Following purification, it was determined that the solvent was best removed by lyophilization to minimize the deterioration of the product. 1H-NMR and ESI-MS results confirm the presence of the product, indicating that the desired ligands have been successfully synthesized.

Additional research requires more extensive characterization of the synthesized ligands before the synthesis of the final product using these ligands. Previous research indicates that this product has a high potential for use as fluorescent surrogates to the corresponding technetium complexes. Fluorescence tests on the rhenium complexes should provide insight on the nature of the coordination of rhenium to the chelate and biological vectors. Extensive in vitro and in vivo studies will require completion before these complexes can be used in a clinical setting.

Creative Commons License

Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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