Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.

Detalhes bibliográficos
Autor(a) principal: Pais, João Pedro de Almeida
Data de Publicação: 2011
Tipo de documento: Dissertação
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10451/8682
Resumo: Tese de mestrado em Química, apresentada à Universidade de Lisboa, através da Faculdade de Ciências, 2011
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spelling Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.QuímicaTeses de mestrado - 2011Tese de mestrado em Química, apresentada à Universidade de Lisboa, através da Faculdade de Ciências, 2011In previous work, a series of 2,6-dideoxy glycosides have demonstrated antibacterial potential mainly against Bacillus species, Enterococcus faecalis and Listeria monocytogenes. The present research is directed towards the synthesis of new 2,6-dideoxy glycosides and analogs, in order to build a small library of compounds providing novel structure-activity relationships, aiming to understand the mode of action of such compounds. In a parallel pathway, the study of the biological effect of such compounds and the induced metabolic changes will ultimately allow a target-guided synthesis, where the converging pathways will meet to give a novel class of antibiotics. The first steps were given using a phenotypic approach to further understand the changes in the bacterial metabolism induced by this type of compounds. Meanwhile, the synthesis of novel derivatives using the most active compound as scaffold was performed, and the assessment of their antibacterial capacity provided new data for a solid structure-activity relationship study. In this work we present a synthetic strategy for 2,6-dideoxy glycosides based on reaction of 6-deoxyglycals with a variety of alcohols catalysed by triphenylphosphane hydrobromide. The antibacterial activity exhibited by these new compounds was evaluated by agar dilution plates and microdilution methods. In addition, a phenotypic microarray assay was also performed, in order to further understand the biological effects of the synthesized compounds over Bacillus cereus. The first results obtained suggest that the mechanism of action is associated with the cell membrane or its components, confirming dodecyl 2,6-dideoxy-α-L-arabino-hexopyranoside as the compound with the best antimicrobial activity over B. cereus strains. Once the rise of bacterial resistance is a real problem of public health, the demand for new antibiotics with new mechanisms of action is growing, to which the present research intends to answer.Rauter, Amélia Pilar Grases Santos Silva, 1950-Dias, Ricardo Pedro MoreiraRepositório da Universidade de LisboaPais, João Pedro de Almeida2013-06-25T13:32:23Z20112011-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfhttp://hdl.handle.net/10451/8682enginfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-08T15:52:33Zoai:repositorio.ul.pt:10451/8682Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:33:05.952608Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
title Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
spellingShingle Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
Pais, João Pedro de Almeida
Química
Teses de mestrado - 2011
title_short Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
title_full Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
title_fullStr Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
title_full_unstemmed Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
title_sort Synthesis and biological study of deoxy glycosides with potential antimicrobial activity against Bacillus spp.
author Pais, João Pedro de Almeida
author_facet Pais, João Pedro de Almeida
author_role author
dc.contributor.none.fl_str_mv Rauter, Amélia Pilar Grases Santos Silva, 1950-
Dias, Ricardo Pedro Moreira
Repositório da Universidade de Lisboa
dc.contributor.author.fl_str_mv Pais, João Pedro de Almeida
dc.subject.por.fl_str_mv Química
Teses de mestrado - 2011
topic Química
Teses de mestrado - 2011
description Tese de mestrado em Química, apresentada à Universidade de Lisboa, através da Faculdade de Ciências, 2011
publishDate 2011
dc.date.none.fl_str_mv 2011
2011-01-01T00:00:00Z
2013-06-25T13:32:23Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10451/8682
url http://hdl.handle.net/10451/8682
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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