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Master's Dissertation
DOI
https://doi.org/10.11606/D.75.2020.tde-04022020-164900
Document
Author
Full name
Jéssica Maria de Almeida
Institute/School/College
Knowledge Area
Date of Defense
Published
São Carlos, 2019
Supervisor
Committee
Deflon, Victor Marcelo (President)
Corbi, Pedro Paulo
Godoy Netto, Adelino Vieira de
Rocha, Fillipe Vieira
Title in Portuguese
Síntese e caracterização estrutural de novos complexos de rênio (I) e tecnécio-99m (I) com potencial aplicação na medicina nuclear
Keywords in Portuguese
complexo
radiação
radiofármacos
tecnécio-99m (I) e rênio (I)
Abstract in Portuguese

Usando os conceitos de química de coordenação, introduzidos por Alfred Werner, e com o avanço da ciência que compreende a relação de compostos inorgânicos em sistemas biológicos, a bioinorgânica, que encontra aplicações em diversas áreas, inclusive na medicina nuclear, podemos propor estudos visando à preparação de novos complexos metálicos como potenciais radiofármacos e analisar o seu comportamento no organismo. Dessa forma, este trabalho consiste na síntese e caracterização do ligante inédito 2-hidroxi-5-metil-3-((metil(2-(metilamino)etil)amino)benzaldeído (HL) e o seu cloridrato (HL-HCl), e dos respectivos complexos de rênio, [ReBr(CO)3(HL)] e tecnécio-99m, [99mTcCl(CO)3(HL)]. A síntese do ligante foi realizada a partir dos compostos 2-hidroxi-3-clorometil-5-metilbenzaldeído e N,N'-(dimetil)etilenodiamina; a síntese foi realizada em três etapas e envolveu a monoproteção do grupo amina com o Di-terc-butil dicarbonato (Boc). A síntese do complexo de rênio foi realizada usando o cloridrato recém-sintetizado com o complexo precursor [Re(OH2)3(CO)3]Br. A caracterização dos compostos se deu pelas técnicas de: espectroscopia de absorção na região do infravermelho e UV-Visível, ressonância magnética nuclear (1H, 13C, COSY, DEPT-135 e HSQC), condutimetria, espectrometria de massas e difração de raios X de monocristal. Também foram realizadas simulações computacionais do ligante e dos compostos de coordenação que tiveram por objetivo corroborar com os resultados experimentais e ampliar o entendimento da interação do radiocomplexo em sistemas biológicos. Após a obtenção do complexo de rênio (I), foram realizadas as marcações utilizando o radioisótopo tecnécio-99m. As marcações apresentaram resultados satisfatórios, tendo valor máximo de pureza radioquímica de 83%. Ensaios avaliando a estabilidade do [99mTc(OH2)3(CO)3]Cl e as marcações utilizando radiação de micro-ondas também apresentaram bons resultados. Os resultados até aqui obtidos mostraram-se promissores para aplicação do radiocomplexo na medicina nuclear de diagnóstico.

Title in English
Synthesis and structural characterization of new rhenium and technetium- 99m complexes with potential application in nuclear medicine
Keywords in English
complex
radiation
radiopharmaceuticals
technetium-99m (I) and rhenium (I)
Abstract in English
Using concepts of coordination chemistry, introduced by Alfred Werner, and withthe advancement of the science that comprises the relationship of inorganic compoundsin biological systems, bioinorganic chemistry, which finds applications in several areas,including in nuclear medicine, we can propose new studies as potentialradiopharmaceuticals and analyze their behavior in the human body. Thus, this workconsists on the synthesis and characterization of the new Ligand 2-hydroxy-5-methyl-3-((methyl (2-(methylamino)ethyl) amino) benzaldehyde (HL), its correspondingchlorohydrate salt, and the respective rhenium (I) - [ReBr(CO)3(HL)] - and technetium-99m (I), - [99mTcCl(CO)3(HL)] - complexes.The synthesis of the ligand (HL) was carried out from the 2-hydroxy-3-chloromethyl-5-methylbenzaldehyde and N, N'-(dimethyl)ethylenediamine compounds;three steps were performed, involving the mono-protection of the amine group with Ditert-butyl dicarbonate (Boc). The synthesis of the rhenium (I) complex was performedusing the newly synthesized ligand-salt with the precursor complex [Re(OH2)3(CO)3]Br.The characterization of the compounds was carried out by infrared and UVVisiblespectroscopies, nuclear magnetic resonance (1H, 13C, COSY, DEPT-135 and HSQC),conductimetry, mass spectrometry, and single crystal X-ray diffraction. A ComputationalSimulations of the ligand and coordination compounds were also carried out with theobjective of corroborating to the experimental work, broadening the understanding ofthe radiocomplex interaction in biological systems.After obtaining the rhenium (I) complex, the labeling was performed using thetechnetium-99m (I) radioisotope. The markers presented satisfactory results, having amaximum radiochemical purity of 83%. Assays evaluating the stability of[99mTc(OH2)3(CO)3]Cl and the labeling using microwave irradiation showed good results.However, the results obtained so far have been encouraging and have demonstratedpotential for applications in diagnostic nuclear medicine.
 
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Publishing Date
2020-03-11
 
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