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Structural and Functional Studies on the Reactivity of Corms with Plasma Proteins Marino Filipe Alves dos Santos Mestre em Biotecnologia Structural and Functional studies on the Reactivity of CORMs with plasma proteins Dissertação para obtenção do Grau de Doutor em Bioquímica, Especialidade Bioquímica Estrutural Orientador: Doutora Teresa Sacadura Santos-Silva, Investigadora Auxiliar, FCT/UNL Co-orientador: Doutora Maria João Lobo de Reis Madeira Crispim Romão, Professora Catedrática, FCT/UNL Júri Presidente: Prof. Doutora Maria Paula Pires dos Santos Diogo Arguentes: Doutor João Domingos Galamba Correia Doutora Isabel Maria Travassos de Almeida de Jesus Bento Vogais: Prof. Doutor Carlos José Rodrigues Crispim Romão Prof. Doutor João Emídio da Silva da Costa Pessoa Prof. Doutor Eurico José da Silva Cabrita Doutor Tiago Miguel Guerra Miranda Bandeiras Doutora Teresa Sacadura Santos Silva Julho de 2016 Marino Filipe Alves dos Santos Mestre em Biotecnologia Structural and Functional studies on the Reactivity of CORMs with plasma proteins Dissertação para obtenção do Grau de Doutor em Bioquímica, Especialidade Bioquímica Estrutural Orientador: Doutora Teresa Sacadura Santos-Silva, Investigadora Auxiliar, FCT/UNL Co-orientador: Doutora Maria João Lobo de Reis Madeira Crispim Romão, Professora Catedrática, FCT/UNL Júri Presidente: Prof. Doutora Maria Paula Pires dos Santos Diogo Arguentes: Doutor João Domingos Galamba Correia Doutora Isabel Maria Travassos de Almeida de Jesus Bento Vogais: Prof. Doutor Carlos José Rodrigues Crispim Romão Prof. Doutor João Emídio da Silva da Costa Pessoa Prof. Doutor Eurico José da Silva Cabrita Doutor Tiago Miguel Guerra Miranda Bandeiras Doutora Teresa Sacadura Santos Silva Julho de 2016 Structural and Functional studies on the Reactivity of CORMs with plasma proteins “Structural and Functional studies on the Reactivity of CORMs with plasma proteins” “Copyright” em nome de Marino Filipe Alves dos Santos, da FCT/UNL e da UNL A Faculdade de Ciências e Tecnologia e a Universidade Nova de Lisboa têm o direito, perpétuo e sem limites geográficos, de arquivar e publicar esta dissertação através de exemplares impressos reproduzidos em papel ou de forma digital, ou por qualquer outro meio conhecido ou que venha a ser inventado, e de a divulgar através de repositórios científicos e de admitir a sua cópia e distribuição com objectivos educacionais ou de investigação, não comerciais, desde que seja dado crédito ao autor e editor. Structural and Functional studies on the Reactivity of CORMs with plasma proteins . Structural and Functional studies on the Reactivity of CORMs with plasma proteins O trabalho apresentado nesta Dissertação foi realizado com o apoio financeiro da Fundação para a Ciência e Tecnologia (FCT–MEC), através da atribuição da Bolsa de Doutoramento individual SFRH/BD/77894/2011 e do projecto PTDC/QUI-BIQ/117799/2010. O trabalho desenvolvido ao longo da presente Dissertação resultou na publicação dos seguintes artigos em revistas internacionais: 1) – Marino F. A. Santos, João D. Seixas, Abhik Mukhopadhyay, Patrícia M. Reis, Maria J. Romão, 2+ Carlos C. Romão, Teresa Santos-Silva, New insights into the chemistry of fac-[Ru(CO)3] fragments in biologically relevant conditions: The CO releasing activity of [Ru(CO)3Cl2(1,3-thiazole)], and the X-ray crystal structure of its adduct with lysozyme, Journal of Inorganic Biochemistry 2012, 117, 285- 291. 2) – Sameena Mehtab, Gisela Gonçalves, Somnath Roy, Ana Isabel Tomaz, Teresa Santos-Silva, Marino F.A. Santos, Maria J. Romão, Tamás Jakusch, Tamás Kiss, João Costa Pessoa, Interaction of vanadium (IV) with human serum apo-transferrin, Journal of Inorganic Biochemistry 2013, 121, 187- 195. 3) – João Costa Pessoa, Gisela Gonçalves, Somnath Roy, Isabel Correia, Sameena Mehtab, Marino F.A. Santos, Teresa Santos-Silva, New insights on vanadium binding to human serum transferrin, Inorganica Chimica Acta 2014, 420, 60-68. 4) – Marino F. A. Santos, Isabel Correia, Ana R. Oliveira, Eugenio Garribba, João Costa Pessoa, Teresa Santos-Silva, Vanadium Complexes as Prospective Therapeutics: Structural Characterization of a VIV Lysozyme Adduct, European Journal of Inorganic Chemistry 2014, 2014(21), 3293-3297. 5) – João D. Seixas, Marino F. A. Santos, Abhik Mukhopadhyay, Ana C. Coelho, Patrícia M. Reis, Luís F. Veiros, Ana R. Marques, Nuno Penacho, Ana M. L. Gonçalves, Maria J. Romão, Gonçalo J. L. Bernardes, Teresa Santos-Silva, Carlos C. Romão, A contribution to the rational design of Ru(CO)3Cl2L complexes for in vivo delivery of CO, Dalton Transactions 2015, 44, 5058-5075. 6) – João Costa Pessoa, Eugenio Garribba, Marino F.A. Santos, Teresa Santos-Silva, Vanadium and proteins: uptake, transport, structure, activity and function, Coordination Chemistry Reviews 2015, 301-302, 49-86. Structural and Functional studies on the Reactivity of CORMs with plasma proteins Agradecimentos Acknowledgements “O passado é a chave do futuro.” Foi assim que comecei os Agradecimentos da minha Tese de Mestrado. Quatro anos volvidos, e porque há tradições que se devem manter e preservar, assim começo os Agradecimentos da minha Tese de Doutoramento. Obrigado a todos. E, usando esta tão simples e sucinta expressão, podia ficar por aqui. Todavia, parece-me que se gerou uma infundada expectativa sobre esta secção pelos mais variados quadrantes da sociedade civil que, pese embora o seu manifesto exagero, me faz sentir na obrigação de não a defraudar por simples desistência. Em alternativa, será defraudada lenta e gradualmente à medida que a leitura da secção avance. Quer isto dizer que se não pretendem ficar desiludidos com o conteúdo destas parcas linhas, aconselho vivamente que parem a leitura por aqui embora, claro, sejam livres para continuar por vossa conta e risco. Se, após todo este palavreado, ainda estão a ler, merecem os meus parabéns pela persistência e o meu reparo pela teimosia. Perguntei-me várias vezes qual seria a melhor maneira de começar esta narrativa. Como não a encontrei, opto por uma saída diplomática sublinhando o meu apreço pelo Benfica e por História. O que tem isso a ver com os Agradecimentos? Pouco, mas não se devem perder oportunidades de mostrar o quanto “me envaidece” a fé inabalável no clube que “nunca encontrou rival neste nosso Portugal”. Já a História, tem que aparecer em qualquer apontamento biográfico da minha parte até porque, qual gloriosa epopeia camoniana, esta secção não pretende mais do que registar para a posterioridade todos aqueles que contribuíram de forma decisiva, quiçá, estrutural – um excelente jogo de palavras – para o desenrolar deste trabalho. Posto isto, comecemos (finalmente) os Agradecimentos devidos. À Teresa, como não podia deixar de ser, ficam as primeiras palavras pela entusiástica e abrangente orientação ao longo destes seis anos. Enquanto seu primeiro aluno de Mestrado e de Doutoramento, disse-lhe, algures no espaço e no tempo, algo como que eu seria “o seu primeiro ciclo de refinamento” enquanto orientadora. Muitos alunos depois, acho que tal previsão se confirmou. Espero que, para primeiro refinamento, tenha obtido uns valores de R e Rfree aceitáveis. À professora Maria João Romão, por ter possibilitado a realização desta Tese no grupo de Cristalografia de Proteínas assim como pela sua co-orientação. No meio de tantos assuntos burocráticos, conseguiu nunca deixar o laboratório e respectiva investigação para trás. Ao professor Carlos Romão, agradeço não apenas a sua acção vital no desenvolvimento do projecto dos CORMs, mas também a sua boa disposição e optimismo. À Catarina por todo o (muito) auxílio durante a minha breve estadia no mundo da síntese organometálica. Ao professor João da Costa Pessoa, pela oportunidade de ter contactado com o vasto “mundo do vanádio” e pela prontidão com que sempre respondeu às nossas (muitas) dúvidas. À Isabel, pela medição dos espectros de EPR e disponibilidade para as minhas dúvidas. Tempo agora para recordar que, nos idos tempos de 2011, agradeci a um espaço físico (a sala de BCM) o que, porventura, terá ajudado na popularidade da obra. Poderia agradecer agora à FCT como um todo (o que não seria mentira alguma), mas vou arriscar e eleger dois espaços em específico: os laboratórios 605 e 607 (com uma menção honrosa para o 621). Tal como disse em 2011, é bem possível que a importância dos espaços se deva aos seus ocupantes pelo que agradeço a todos os membros e “amigos” do XTAL pela ajuda ao longo desta Tese. Desde a Ana Luísa, a Angelina e a Isabel, todos deixaram a sua marca como se pretende transmitir de seguida. I Structural and Functional studies on the Reactivity of CORMs with plasma proteins Às “minhas” alunas de Projecto – Joana, Rita e Marta – pela valiosa oportunidade de exploração desumana que me proporcionaram (deve ler-se “pela sua contribuição para os resultados”). To Abhik for his availability to help me, first in the lab and then directly from the PDBe headquarters. To Shabir for the tips and patience in my first trips to the Synchrotron and for the dinners in one of the fanciest French restaurants: Pizza Hut at Lyon Airport. Ao Jorge, pelos seus mordazes e pertinentes comentários da vida em geral bem como por todo o “apoio moral” que nunca me negou nos (raros a tender para raríssimos) resultados menos conseguidos do Benfica. Que a Estrutura esteja contigo! À Cecília, por todas as encomendas, orçamentos, cristais congelados, soluções, dicas de cristalização, manutenção e operação do robot, envios de dewars e organização logístico-moral de tantos e tantos eventos. Tomara o Quartzy conseguir tal eficiência. A um excelente Trio d’Ataque pós-doutoral sempre com “a genica que as engrandece”: à Benedita, à Catarina e à Márcia. À Benedita, pelas eloquentes conversas de fim de tarde e salutares tentativas (vãs é certo) de me instruir em diferentes variantes sócio-artístico-culturais. À Catarina, pela organização de vários pequenos/grandes aspectos do dia-a-dia do laboratório e pelo passeio ao SLS. À Márcia, pelas peripécias no Diamond (já incluindo o Miguel), pelas (muitas) dicas de SAXS e pela já longínqua paciência enquanto “orientadora” aquando da minha chegada ao laboratório. À Diana Vieira, pela ajuda de longa data que se prolongou pelo doutoramento – em Portugal (desde as aulas até ao passeio a Coimbra) ou em Inglaterra (com o jantar de boas-vindas).
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