Functionalized BODIPY derivatives as potential fluorescent labels

Detalhes bibliográficos
Autor(a) principal: Gonçalves, R.
Data de Publicação: 2018
Outros Autores: Nogueira, M., Costa, Susana P. G., Raposo, M. Manuela M.
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/57472
Resumo: Labels can be attached to proteins, for example antibodies, which accumulate in specific organs for imaging in animals and human subjects. However, there is a growing realization that imaging events in cells and whole organisms by fluorescence is limited by the accessible probes. 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes tend to be strongly UV-absorbing small molecules that emit relatively sharp fluorescence peaks with high quantum yields. They are relatively insensitive to the polarity and pH of their environment and are reasonably stable to physiological conditions. Moreover, small modifications to their structures enable tuning of their fluorescence characteristics. Therefore, these dyes are widely used to label proteins and DNA, among others. Consequently, there is the potential that modifications to the BODIPY framework will lead to probes that can be used more effectively for imaging in living cells and whole organisms, but that it is still largely unrealized. Having in mind earlier studies, by other groups, and also the research developed recently by our group, we report in this work the synthesis and evaluation of the optical properties of BODIPY derivatives having in mind their potential application as novel fluorescent probes for the detection of a wide range of analytes, such as neutral molecules and ions, as well for bio-imaging in living cells.
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spelling Functionalized BODIPY derivatives as potential fluorescent labelsSynthesisBODIPYChemosensorsFluorescencefluorescent probespyrroleLabellingCiências Naturais::Ciências QuímicasLabels can be attached to proteins, for example antibodies, which accumulate in specific organs for imaging in animals and human subjects. However, there is a growing realization that imaging events in cells and whole organisms by fluorescence is limited by the accessible probes. 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes tend to be strongly UV-absorbing small molecules that emit relatively sharp fluorescence peaks with high quantum yields. They are relatively insensitive to the polarity and pH of their environment and are reasonably stable to physiological conditions. Moreover, small modifications to their structures enable tuning of their fluorescence characteristics. Therefore, these dyes are widely used to label proteins and DNA, among others. Consequently, there is the potential that modifications to the BODIPY framework will lead to probes that can be used more effectively for imaging in living cells and whole organisms, but that it is still largely unrealized. Having in mind earlier studies, by other groups, and also the research developed recently by our group, we report in this work the synthesis and evaluation of the optical properties of BODIPY derivatives having in mind their potential application as novel fluorescent probes for the detection of a wide range of analytes, such as neutral molecules and ions, as well for bio-imaging in living cells.Thank are due to Fundação para a Ciência e Tecnologia (Portugal) and FEDER COMPETE for financial support through Centro de Química (UID/ QUI/0686/2016). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT.info:eu-repo/semantics/publishedVersionMDPIUniversidade do MinhoGonçalves, R.Nogueira, M.Costa, Susana P. G.Raposo, M. Manuela M.20182018-01-01T00:00:00Zconference objectinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/1822/57472engGonçalves, R.; Nogueira, M.; Costa, S. P. G.; Raposo, M. M. M.; Functionalized BODIPY derivatives as potential fluorescent labels. 22nd International Electronic Conference on Synthetic Organic Chemistry 1 a 30 de novembro de 2018, Sciforum Electronic Conferences Series, https://sciforum.net/paper/view/conference/5701https://sciforum.net/paper/view/conference/5701info: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:RCAAP2024-05-11T06:31:50Zoai:repositorium.sdum.uminho.pt:1822/57472Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-11T06:31:50Repositório 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 Functionalized BODIPY derivatives as potential fluorescent labels
title Functionalized BODIPY derivatives as potential fluorescent labels
spellingShingle Functionalized BODIPY derivatives as potential fluorescent labels
Gonçalves, R.
Synthesis
BODIPY
Chemosensors
Fluorescence
fluorescent probes
pyrrole
Labelling
Ciências Naturais::Ciências Químicas
title_short Functionalized BODIPY derivatives as potential fluorescent labels
title_full Functionalized BODIPY derivatives as potential fluorescent labels
title_fullStr Functionalized BODIPY derivatives as potential fluorescent labels
title_full_unstemmed Functionalized BODIPY derivatives as potential fluorescent labels
title_sort Functionalized BODIPY derivatives as potential fluorescent labels
author Gonçalves, R.
author_facet Gonçalves, R.
Nogueira, M.
Costa, Susana P. G.
Raposo, M. Manuela M.
author_role author
author2 Nogueira, M.
Costa, Susana P. G.
Raposo, M. Manuela M.
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Gonçalves, R.
Nogueira, M.
Costa, Susana P. G.
Raposo, M. Manuela M.
dc.subject.por.fl_str_mv Synthesis
BODIPY
Chemosensors
Fluorescence
fluorescent probes
pyrrole
Labelling
Ciências Naturais::Ciências Químicas
topic Synthesis
BODIPY
Chemosensors
Fluorescence
fluorescent probes
pyrrole
Labelling
Ciências Naturais::Ciências Químicas
description Labels can be attached to proteins, for example antibodies, which accumulate in specific organs for imaging in animals and human subjects. However, there is a growing realization that imaging events in cells and whole organisms by fluorescence is limited by the accessible probes. 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes tend to be strongly UV-absorbing small molecules that emit relatively sharp fluorescence peaks with high quantum yields. They are relatively insensitive to the polarity and pH of their environment and are reasonably stable to physiological conditions. Moreover, small modifications to their structures enable tuning of their fluorescence characteristics. Therefore, these dyes are widely used to label proteins and DNA, among others. Consequently, there is the potential that modifications to the BODIPY framework will lead to probes that can be used more effectively for imaging in living cells and whole organisms, but that it is still largely unrealized. Having in mind earlier studies, by other groups, and also the research developed recently by our group, we report in this work the synthesis and evaluation of the optical properties of BODIPY derivatives having in mind their potential application as novel fluorescent probes for the detection of a wide range of analytes, such as neutral molecules and ions, as well for bio-imaging in living cells.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-01-01T00:00:00Z
dc.type.driver.fl_str_mv conference object
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/57472
url http://hdl.handle.net/1822/57472
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Gonçalves, R.; Nogueira, M.; Costa, S. P. G.; Raposo, M. M. M.; Functionalized BODIPY derivatives as potential fluorescent labels. 22nd International Electronic Conference on Synthetic Organic Chemistry 1 a 30 de novembro de 2018, Sciforum Electronic Conferences Series, https://sciforum.net/paper/view/conference/5701
https://sciforum.net/paper/view/conference/5701
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.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
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 mluisa.alvim@gmail.com
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