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Universidade Estadual De Campinas Instituto De UNIVERSIDADE ESTADUAL DE CAMPINAS INSTITUTO DE QUÍMICA FABIÁN GILBERTO VILLALTA ROMERO AŃLISE ESTRUTURAL E FUNCIONAL DE METALO (SVMP) E SERINA PROTEASES (SVSP) DE VENENOS DE SERPENTES CAMPINAS 2016 FABIÁN GILBERTO VILLALTA ROMERO AŃLISE ESTRUTURAL E FUNCIONAL DE METALO (SVMP) E SERINA PROTEASES (SVSP) DE VENENOS DE SERPENTES Tese de Doutorado apresentada ao Instituto de Química da Universidade Estadual de Campinas como parte dos requisitos exigidos para a obtenção do título de Doutor(a) em Ciências Orientador(a): Prof(a). Dr(a). Ljubica Tasic Coorientador(a): Prof(a). Dr(a). Goran Neshich ESTE EXEMPLAR CORRESPONDE À VERSÃO FINAL DA TESE DEFENDIDA PELO(A) ALUNO(A) FABIÁN GILBERTO VILLALTA ROMERO, E ORIENTADA PELO(A) PROF(A). DR(A). LJUBICA TASIC CAMPINAS 2016 BANCA EXAMINADORA Profa. Dra. Ljubica Tasic (Orientadora) Profa. Dra. Mirian Akemi Furuie Hayashi (UNIFESP) Profa. Dra. Giselle Zenker Justo (UNIFESP-Diadema) Profa. Dra. Taicia Pacheco Fill (IQ-UNICAMP) Profa. Dra. Cátia Cristina Capêlo Ornelas Megiatto (IQ-UNICAMP) A Ata da defesa com as respectivas assinaturas dos membros encontra-se no processo de vida acadêmica do(a) aluno(a). Este exemplar corresponde à redação final da Tese de Doutorado defendida pelo aluno FABIÁN GILBERTO VILLALTA ROMERO, aprovada pela Comissão Julgadora em 25 de fevereiro de 2016. Dedico este trabalho à minha família, que foi a parte dele em todos momentos. Agradecimentos A Deus pela vida. À minha família pelo apoio e por me motivar a continuar e não desistir. À minha professora e orientadora, Ljubica Tasic (Buba), pela oportunidade de ser a parte do Laboratório de Química Biológica (LQB), realizar a pesquisa no Brasil e pela ajuda dada em todos os momentos. Ao pessoal do Laboratório I-250, ao professor Nelson Durán e seus estudantes (Elias, Ana Paula, Jeanifer, Ana Maria, Dani Ridolfi, Camila, Amauri, Patricia, Paula e Carol). Ao nosso técnico do laboratório, Francisco Camargo, pela sua amizade e por ter me socorrido quando fui atropelado. A todos os colegas que passaram pelo LQB: Junko, Ana Paula, Almas, Dani Pott, Dani Cypriano, Banny, João, Stephanie, Flávia, Guillerme, William, Antônio, Raphael, Natália, Willian, Paula, Gilberto, Verônica, Caio, Mayra, Lucimara, Danijela e Boris. A Lillian por seus brigadeiros, a palha italiana e sua ajuda com meu português. Aos meus colegas de pesquisa Roney, Raniery e Marina por toda ajuda. E não posso esquecer a nossa “cafeteira”, que sempre tinha o café pronto na hora certa. Aos meus treinadores Luiz, Giovanna, Marina, Guima, Bruno e aos meus colegas de triathlon Atila, Martina, Diego, Ricardo, André, Laura, Joana, Ruam, Matheus, Luciane, Jorge, Andrew, Lucia, Sofia, Jadisha, Marina e em especial ao Ricardo e a Monica por tantos momentos compartilhados. À Valeria pelos treinos de bike de madrugada. Ao Daijiro e à Patricia por todas suas dicas para melhorar neste belo esporte. Aos colegas de minha antiga república Ricardo, Jadson, Guilherme, Neto, Stephanie, Lucas, Allan, Fernanda e Marina. Aos meus amigos Janainna, Priscilla, Banny, Rafael, Jane, João Paulo e a Teka por me mostrar tanto do Brasil principalmente da gastronomia, música e novas palavras! Mas, principalmente por sua amizade e por compartilhar tantos jantares onde não poderia faltar uma berinjela!! Ao pessoal da Embrapa, Luiz, Salim, Ignacio, Ivan, Jardine e principalmente ao professor Goran pela oportunidade de usar tanto recurso computacional e por todo o aprendizado. Ao professor Arni, Rafael e a Mônika por toda sua ajuda na tentativa de cristalizar “minhas” proteínas. Ao Paulino por sua ajuda na purificação das serina proteases. Ao pessoal do Instituto de Química, professores e técnicos de laboratório, em especial a Claudia Martelli, Sonia Fanelli, Anderson Pedrosa, Gustavo Shimamoto e Paula Pilli. E ao pessoal da CPG. Aos visitantes internacionais Raphael e Nixson do Chile, Ricardo e Renier de Cuba por sua amizade. Ao professor Stephen Hyslop e suas estudantes Norma e Bia pela ajuda no ensaio de inibição de angiogênese em membrana corionalantóide de embrião de galinha (in ovo). À professora Giselle Zenker pela ajuda nos ensaios em células endoteliais de aorta de coelho. Ao pessoal do Instituto Clodomiro Picado, senhor José María, Alexandra Rucavado, Teresa Escalante, Erika Camacho, e professor Bruno Lomonte pela ajuda e conselhos. À María e ao Raúl por trazer minha bike, a Tercipelo, e alguns Tamalitos lembrando-me as cosas boas do Natal em Costa Rica! À Karina por sua visita e por trazer o famoso molho Salsa Lizano e café da Costa Rica. Ao pessoal externo a Lab LQB Luiz, Leandro, Ana Carolina, Diego, Marcelo, Amanda. Ao senhor João e a sua família em Cruzilia por me permitir conhecer a cultura mineira e em especial o angu, um prato simples, mas que bem acompanhado é uma delícia! Enfim, a tantas pessoas que tornaram muito agradável minha estadia no Brasil, muito obrigado por tudo. Resumo As picadas por serpentes s̃o classificadas como doenças negligenciadas pela Organização Munidial de Saúde (OMS). Além de ser uma quest̃o de sáde ṕblica, a peconha ou veneno de serpentes (SV) é particularmente interessante por apresentar atividades bioqúmicas e farmacológicas ́nicas. Nossa pesquisa abrange os estudos acerca de seis proteases de SV das classes: metalo (SVMP) e serina proteases (SVSP), que foram isoladas de tres serpentes: Bothrops asper (SVMP, BaP1), Crotalus simus (SVMP, PIII; SVSP-I e SVSP-II) e Crotalus durissus cumanensis (SVSP, Cd SI e Cd SII). Na primeira parte deste trabalho foram utilizadas as técnicas de dicrósmo circular e fluorescencia para caracterizac̃o biof́sica das proténas alvo. Foi verificado o papel de ́ons de cálcio (II) na estabilizac̃o da estrutura e atividade das duas SVMP. Na segunda parte, utilizando as técnicas in silico de Screening virtual das bibliotecas Zinc, ChemBL e PubChem, foram propostos cinco compostos como potenciais inibidores da BaP1. Destes, três compostos foram testados em ensaios in vitro e dois inibiram a atividade proteoĺtica da BaP1. Usando metodologia similar, a hesperitina foi proposta como um inibidor potente para as SVSP, in silico e in vitro. Dessa forma, esses compostos poder̃o ser úteis no tratamento de envenenamentos. A terceira parte deste trabalho consistiu na análise comparativa de estruturas 3D de SVMP utilizando ferramentas de biologia computacional e na caracterizaç̃o das diferenças entre as proténas que provocam ou ño a hemorragia em acidentes ofídicos. Finalmente, na quarta e última parte, estudamos a atividade das SVMP, BaP1 e PIII, perante a inibic̃o da formac̃o de capilares sangúneos e verificamos que ambas mostram potencial farmacológico para terapia antiangiogenica. Abstract Snake bites are classified as neglected diseases according to the WHO. As well as a public health issue, the snake venom (SV) is particularly interesting because it presents unique biochemical and pharmacological activities. Our research covers the study of six SV proteases, metalloproteases (SVMP) and serine proteases (SVSP), isolated from three snakes: Bothrops asper (SVMP, BaP1), Crotalus simus (SVMP, PIII; SVSP-I and SVSP-II) and Crotalus durissus cumanensis (SVSP, Cd SI and Cd SII). The circular dichroism and fluorescence techniques were used for the biophysical characterization of the target proteins. The role of calcium (II) ions in stabilizing the structure and activity of the two SVMP was verified. In the second part of this work, using the Virtual Screening techniques, the libraries Zinc, ChemBL and PubChem were screened and five compounds have been proposed as good in silico inhibitors of BaP1. Among these, three were tested in vitro assays and two showed complete inhibition of the proteolytic activity of BaP1. Using similar methodology, the hesperetin has been proposed as a potent inhibitor for the SVSP, both in silico and in vitro. Thus, these compounds have the potential to aid in the anti-poisoning treatments. The third part of this work consisted of the comparative analysis of SVMP 3D structures by computational biology tools, and the differences between the proteins that provoke or not cause hemorrhagic effects were characterized. Finally, we investigated the activity of SVMP, BaP1 and PIII in the inhibition of the formation of blood capillaries and found that both tested proteins show pharmacological potential for antiangiogenic therapy. Lista de figuras Figura 1 Nomenclatura específica para o substrato da protease, em que os resíduos de aminoácidos no substrato são numerados para fora do local de clivagem como ··· -P4 -P3 -P2-P1-P1'-P2'-P3'-P4'- ···, e o local de clivagem é destacado pela seta preta, entre P1 eP1 '. ________________________ 30 Figura 2 Esquema de classificação das MEPs de acordo com a sua assinatura de ligação de zinco conhecidas, incluindo apenas as famílias de proteases para as quais as estruturas tridimensionais estão disponíveis. _______________________________________________________________ 32 Figura 3 (A) A figura representa a coordenação do íon zinco (II) a três histidinas e a uma molécula de água (Lingott et al., 2009). (B) Estrutura da metaloprotease BaP1 (PDB: 1ND1) representada em cartoon onde, em azul são as -hélices, em amarelo as folhas-, e em verde voltas e estruturas randômicas. (C) Topologia do domínio catalítico da metzincina, da família adamalysins/ADAMs, onde o esquema mostra os elementos da estrutura secundária regular. Mostrando as -hélices como cilindros, as folhas-, como flechas, as ligações de hidrogênio e ligações metal-ligante como linhas tracejadas, ligações de dissulfeto como linhas
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