Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://doi.org/10.48797/sl.2023.84 |
Resumo: | Background: Rosamines are a class of fluorescent dyes, structurally related to rhodamines, that are commonly used as fluorophores in biological research since they have high quantum yields, photostability, and sensitivity to changes in their environment [1,2]. Rhodamines can also be derivatized to be coupled with lipids to create fluorescent lipid probes. These probes are useful for visualizing and studying various lipid-related processes, such as lipid metabolism, lipid transport, lipid signaling, and lipid dynamics in real-time [3]. Objective: The aim of the present work was to synthesize and characterize the spectroscopic fluorescence properties of lipids tagged with a rhodamine derivative for assessment of lipid phenomena using liposomes as biomimetic models. Methods: The synthetic strategy envisioned considers the preparation of a rosamine containing a (2-iodoacetyl)piperazin-1-yl moiety (RosPi) that would allow the bioconjugation with the amino group of 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine (POPE). Results: The synthesis of RosPi, based on previously described procedures, was achieved in seven steps in 12% overall yield [4,5]. Firstly, a microwave assisted cyclization of a tetrahydroxybenzophenone in water led to the synthesis of the xanthone intermediate (90% yield). Then, triflic anhydride was used to form the corresponding ditrifilxanthone (94% yield) which in turn reacted with the Boc-piperazine to deliver the aminated xanthene (65%). Nucleophilic addition of 1,3-dimethoxybenzene to the xanthone carbonyl (66%) followed by Boc-deprotection provided the unmasked bisammonium salt (74%). Finally, the salt was reacted with the 2-chloroacetyl chloride to give the diamide (67%) which was transformed into the final iodoacetamide derivative by reaction with sodium iodide (69%). Several attempts for the bioconjugation of RosPi with POPE were performed and purification and structural characterization of the product are in progress. Conclusions: The preparation of RosPi was successfully achieved. The structural characterization and spectroscopy studies of the bioconjugate POPE-RosPi are ongoing. |
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Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic modelsPosterBackground: Rosamines are a class of fluorescent dyes, structurally related to rhodamines, that are commonly used as fluorophores in biological research since they have high quantum yields, photostability, and sensitivity to changes in their environment [1,2]. Rhodamines can also be derivatized to be coupled with lipids to create fluorescent lipid probes. These probes are useful for visualizing and studying various lipid-related processes, such as lipid metabolism, lipid transport, lipid signaling, and lipid dynamics in real-time [3]. Objective: The aim of the present work was to synthesize and characterize the spectroscopic fluorescence properties of lipids tagged with a rhodamine derivative for assessment of lipid phenomena using liposomes as biomimetic models. Methods: The synthetic strategy envisioned considers the preparation of a rosamine containing a (2-iodoacetyl)piperazin-1-yl moiety (RosPi) that would allow the bioconjugation with the amino group of 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine (POPE). Results: The synthesis of RosPi, based on previously described procedures, was achieved in seven steps in 12% overall yield [4,5]. Firstly, a microwave assisted cyclization of a tetrahydroxybenzophenone in water led to the synthesis of the xanthone intermediate (90% yield). Then, triflic anhydride was used to form the corresponding ditrifilxanthone (94% yield) which in turn reacted with the Boc-piperazine to deliver the aminated xanthene (65%). Nucleophilic addition of 1,3-dimethoxybenzene to the xanthone carbonyl (66%) followed by Boc-deprotection provided the unmasked bisammonium salt (74%). Finally, the salt was reacted with the 2-chloroacetyl chloride to give the diamide (67%) which was transformed into the final iodoacetamide derivative by reaction with sodium iodide (69%). Several attempts for the bioconjugation of RosPi with POPE were performed and purification and structural characterization of the product are in progress. Conclusions: The preparation of RosPi was successfully achieved. The structural characterization and spectroscopy studies of the bioconjugate POPE-RosPi are ongoing.IUCS-CESPU Publishing2023-04-21info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://doi.org/10.48797/sl.2023.84https://doi.org/10.48797/sl.2023.84Scientific Letters; Vol. 1 No. Sup 1 (2023)2795-5117reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAPenghttps://publicacoes.cespu.pt/index.php/sl/article/view/84https://publicacoes.cespu.pt/index.php/sl/article/view/84/29Copyright (c) 2023 P. A. M. M. Varandas , A. J. A. Cobb , M. A. Segundo , E. M. P. Silvainfo:eu-repo/semantics/openAccessVarandas , P. A. M. M.Cobb , A. J. A.Segundo , M. A.Silva , E. M. P.2023-04-29T08:46:11Zoai:publicacoes.cespu.pt:article/84Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T17:50:23.843855Repositório 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 of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
title |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
spellingShingle |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models Varandas , P. A. M. M. Poster |
title_short |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
title_full |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
title_fullStr |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
title_full_unstemmed |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
title_sort |
Synthesis of a rosamine-based lipid probe for the study of lipid phenomena in membrane biomimetic models |
author |
Varandas , P. A. M. M. |
author_facet |
Varandas , P. A. M. M. Cobb , A. J. A. Segundo , M. A. Silva , E. M. P. |
author_role |
author |
author2 |
Cobb , A. J. A. Segundo , M. A. Silva , E. M. P. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Varandas , P. A. M. M. Cobb , A. J. A. Segundo , M. A. Silva , E. M. P. |
dc.subject.por.fl_str_mv |
Poster |
topic |
Poster |
description |
Background: Rosamines are a class of fluorescent dyes, structurally related to rhodamines, that are commonly used as fluorophores in biological research since they have high quantum yields, photostability, and sensitivity to changes in their environment [1,2]. Rhodamines can also be derivatized to be coupled with lipids to create fluorescent lipid probes. These probes are useful for visualizing and studying various lipid-related processes, such as lipid metabolism, lipid transport, lipid signaling, and lipid dynamics in real-time [3]. Objective: The aim of the present work was to synthesize and characterize the spectroscopic fluorescence properties of lipids tagged with a rhodamine derivative for assessment of lipid phenomena using liposomes as biomimetic models. Methods: The synthetic strategy envisioned considers the preparation of a rosamine containing a (2-iodoacetyl)piperazin-1-yl moiety (RosPi) that would allow the bioconjugation with the amino group of 2-oleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine (POPE). Results: The synthesis of RosPi, based on previously described procedures, was achieved in seven steps in 12% overall yield [4,5]. Firstly, a microwave assisted cyclization of a tetrahydroxybenzophenone in water led to the synthesis of the xanthone intermediate (90% yield). Then, triflic anhydride was used to form the corresponding ditrifilxanthone (94% yield) which in turn reacted with the Boc-piperazine to deliver the aminated xanthene (65%). Nucleophilic addition of 1,3-dimethoxybenzene to the xanthone carbonyl (66%) followed by Boc-deprotection provided the unmasked bisammonium salt (74%). Finally, the salt was reacted with the 2-chloroacetyl chloride to give the diamide (67%) which was transformed into the final iodoacetamide derivative by reaction with sodium iodide (69%). Several attempts for the bioconjugation of RosPi with POPE were performed and purification and structural characterization of the product are in progress. Conclusions: The preparation of RosPi was successfully achieved. The structural characterization and spectroscopy studies of the bioconjugate POPE-RosPi are ongoing. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-04-21 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://doi.org/10.48797/sl.2023.84 https://doi.org/10.48797/sl.2023.84 |
url |
https://doi.org/10.48797/sl.2023.84 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
https://publicacoes.cespu.pt/index.php/sl/article/view/84 https://publicacoes.cespu.pt/index.php/sl/article/view/84/29 |
dc.rights.driver.fl_str_mv |
Copyright (c) 2023 P. A. M. M. Varandas , A. J. A. Cobb , M. A. Segundo , E. M. P. Silva info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Copyright (c) 2023 P. A. M. M. Varandas , A. J. A. Cobb , M. A. Segundo , E. M. P. Silva |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
IUCS-CESPU Publishing |
publisher.none.fl_str_mv |
IUCS-CESPU Publishing |
dc.source.none.fl_str_mv |
Scientific Letters; Vol. 1 No. Sup 1 (2023) 2795-5117 reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799131583768166400 |