6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules
Autor(a) principal: | |
---|---|
Data de Publicação: | 2022 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10174/33124 https://doi.org/Pereira, F.; Lourenço, A.; Aires-de-Sousa, J.; Ferreira, L.M.; Marques, M.M.B.; Sousa, E.; Branco, P.S. 14th Edition of the Nacional Organic Chemistry Meeting and 7th Edition of the Nacional Therapeutic Chemistry Meeting. Chem. Proc. 2022, 11, 1, p62. https://doi.org/10.3390/ chemproc2022011001 https://doi.org/10.3390/ chemproc2022011001 |
Resumo: | Cellular biology, medicine, pharmacy, environmental sciences and other important scientific areas require highly sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, amino acids, proteins, lipids, carbohydrates, and other biomolecules. Of all sensitive analytical techniques, fluorescent labeling presents numerous advantages as it allows the use of small sample quantities as well as the respective fluorescent labels [1,2]. The availability and the development of new fluorophores are now enabling previously impossible studies of cellular processes and the detection of specific components of complex biomolecular assemblies with selectivity and exquisite sensitivity, in vitro and in vivo, as well the analysis of their interactions [3]. In this context, due to Chem. Proc. 2022, 11, 1 63 of 127 the high cost of the available commercial fluorescent labels, coumarin derivatives can be a solution to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined with large Stokes shifts. In this work, we developed an effective synthetic strategy to produce new red-shifted 4-styryl coumarins using 7-diethylamino-4- methylcoumarin (1) as a starting material. These could be used to produce fluorescent labels for biomolecules. The main synthetic strategy to obtain 4-styryl coumarins was based on the high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl- 2H-chromen-2-ylidene)malononitrile (3), that enable aldol condensation reactions. The mentioned dicyanomethylene-coumarinylmethyl derivative, with a higher bathochromic shift than 100 nm when compared with its precursor, was obtained by the incorporation of two cyano groups in position 2 after the thionation of the carbonyl group of lactone. With the objective to extend the delocalization of the -electron system, we have designed and synthesized new 4-styryl coumarin derivatives, with absorption and emission at long wavelengths, combined with large Stokes shifts, using a simple, low-cost and efficient synthetic strategy (Scheme 1). sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, proteins, lipids, carbohydrates, and other biomolecules. Of all sensitive analytical techniques, presents numerous advantages as it allows the use of small sample quantities as well as the respective labels [1,2]. The availability and the development of new fluorophores are now enabling previously studies of cellular processes and the detection of specific components of complex biomolecular selectivity and exquisite sensitivity, in vitro and in vivo, as well the analysis of their interactions context, due to the high cost of the available commercial fluorescent labels, coumarin derivatives to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined Stokes shifts. In this work, we developed an effective synthetic strategy to produce new red-shifted coumarins using 7-diethylamino-4-methylcoumarin (1) as a starting material. These could be fluorescent labels for biomolecules. The main synthetic strategy to obtain 4-styryl coumarins high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl-2H-chromen-ylidene)malononitrile (3), that enable aldol condensation reactions. The mentioned dicyanomethylenecoumarinylmethyl derivative, with a higher bathochromic shift than 100 nm when compared with was obtained by the incorporation of two cyano groups in position 2 after the thionation of the the lactone. With the objective to extend the delocalization of the π-electron system, we have synthesized new 4-styryl coumarin derivatives, with absorption and emission at long wavelengths, large Stokes shifts, using a simple, low-cost and efficient synthetic strategy (Scheme 13). Scheme 13. Synthesis of the 4-styryl coumarin derivatives |
id |
RCAP_c05d0095661908b08ae65bb32af67bb2 |
---|---|
oai_identifier_str |
oai:dspace.uevora.pt:10174/33124 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomoleculesorganic synthesisCellular biology, medicine, pharmacy, environmental sciences and other important scientific areas require highly sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, amino acids, proteins, lipids, carbohydrates, and other biomolecules. Of all sensitive analytical techniques, fluorescent labeling presents numerous advantages as it allows the use of small sample quantities as well as the respective fluorescent labels [1,2]. The availability and the development of new fluorophores are now enabling previously impossible studies of cellular processes and the detection of specific components of complex biomolecular assemblies with selectivity and exquisite sensitivity, in vitro and in vivo, as well the analysis of their interactions [3]. In this context, due to Chem. Proc. 2022, 11, 1 63 of 127 the high cost of the available commercial fluorescent labels, coumarin derivatives can be a solution to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined with large Stokes shifts. In this work, we developed an effective synthetic strategy to produce new red-shifted 4-styryl coumarins using 7-diethylamino-4- methylcoumarin (1) as a starting material. These could be used to produce fluorescent labels for biomolecules. The main synthetic strategy to obtain 4-styryl coumarins was based on the high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl- 2H-chromen-2-ylidene)malononitrile (3), that enable aldol condensation reactions. The mentioned dicyanomethylene-coumarinylmethyl derivative, with a higher bathochromic shift than 100 nm when compared with its precursor, was obtained by the incorporation of two cyano groups in position 2 after the thionation of the carbonyl group of lactone. With the objective to extend the delocalization of the -electron system, we have designed and synthesized new 4-styryl coumarin derivatives, with absorption and emission at long wavelengths, combined with large Stokes shifts, using a simple, low-cost and efficient synthetic strategy (Scheme 1). sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, proteins, lipids, carbohydrates, and other biomolecules. Of all sensitive analytical techniques, presents numerous advantages as it allows the use of small sample quantities as well as the respective labels [1,2]. The availability and the development of new fluorophores are now enabling previously studies of cellular processes and the detection of specific components of complex biomolecular selectivity and exquisite sensitivity, in vitro and in vivo, as well the analysis of their interactions context, due to the high cost of the available commercial fluorescent labels, coumarin derivatives to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined Stokes shifts. In this work, we developed an effective synthetic strategy to produce new red-shifted coumarins using 7-diethylamino-4-methylcoumarin (1) as a starting material. These could be fluorescent labels for biomolecules. The main synthetic strategy to obtain 4-styryl coumarins high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl-2H-chromen-ylidene)malononitrile (3), that enable aldol condensation reactions. The mentioned dicyanomethylenecoumarinylmethyl derivative, with a higher bathochromic shift than 100 nm when compared with was obtained by the incorporation of two cyano groups in position 2 after the thionation of the the lactone. With the objective to extend the delocalization of the π-electron system, we have synthesized new 4-styryl coumarin derivatives, with absorption and emission at long wavelengths, large Stokes shifts, using a simple, low-cost and efficient synthetic strategy (Scheme 13). Scheme 13. Synthesis of the 4-styryl coumarin derivativesThe study was performed under the framework of THE SCREAM Project— “Touchstone for Heritage Endangered by Salt Crystallization, a Research Enterprise on the Art of Munch” (ref. FCT-ALT20-03-0145-FEDER-031577) financed by the Portuguese Foundation for Science and Technology (FCT) through National and European Funds.MDPI - Chemistry Proceedings2023-01-04T15:11:36Z2023-01-042022-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10174/33124https://doi.org/Pereira, F.; Lourenço, A.; Aires-de-Sousa, J.; Ferreira, L.M.; Marques, M.M.B.; Sousa, E.; Branco, P.S. 14th Edition of the Nacional Organic Chemistry Meeting and 7th Edition of the Nacional Therapeutic Chemistry Meeting. Chem. Proc. 2022, 11, 1, p62. https://doi.org/10.3390/ chemproc2022011001http://hdl.handle.net/10174/33124https://doi.org/10.3390/ chemproc2022011001porhttps://www.mdpi.com/2673-4583/11/1/1raqueleustaquio98@hotmail.comjpcar@uevora.ptatc@uevora.ptamlp@uevora.pt307Eustáquio, R.Ramalho, J.P.P.Caldeira, A.T.Pereira, A.info: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:RCAAP2024-01-03T19:34:44Zoai:dspace.uevora.pt:10174/33124Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:22:04.103277Repositório 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 |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
title |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
spellingShingle |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules Eustáquio, R. organic synthesis |
title_short |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
title_full |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
title_fullStr |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
title_full_unstemmed |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
title_sort |
6.4. New Red-Shifted 4-Styryl Coumarins as Potential Fluorescent Labels for Biomolecules |
author |
Eustáquio, R. |
author_facet |
Eustáquio, R. Ramalho, J.P.P. Caldeira, A.T. Pereira, A. |
author_role |
author |
author2 |
Ramalho, J.P.P. Caldeira, A.T. Pereira, A. |
author2_role |
author author author |
dc.contributor.author.fl_str_mv |
Eustáquio, R. Ramalho, J.P.P. Caldeira, A.T. Pereira, A. |
dc.subject.por.fl_str_mv |
organic synthesis |
topic |
organic synthesis |
description |
Cellular biology, medicine, pharmacy, environmental sciences and other important scientific areas require highly sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, amino acids, proteins, lipids, carbohydrates, and other biomolecules. Of all sensitive analytical techniques, fluorescent labeling presents numerous advantages as it allows the use of small sample quantities as well as the respective fluorescent labels [1,2]. The availability and the development of new fluorophores are now enabling previously impossible studies of cellular processes and the detection of specific components of complex biomolecular assemblies with selectivity and exquisite sensitivity, in vitro and in vivo, as well the analysis of their interactions [3]. In this context, due to Chem. Proc. 2022, 11, 1 63 of 127 the high cost of the available commercial fluorescent labels, coumarin derivatives can be a solution to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined with large Stokes shifts. In this work, we developed an effective synthetic strategy to produce new red-shifted 4-styryl coumarins using 7-diethylamino-4- methylcoumarin (1) as a starting material. These could be used to produce fluorescent labels for biomolecules. The main synthetic strategy to obtain 4-styryl coumarins was based on the high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl- 2H-chromen-2-ylidene)malononitrile (3), that enable aldol condensation reactions. The mentioned dicyanomethylene-coumarinylmethyl derivative, with a higher bathochromic shift than 100 nm when compared with its precursor, was obtained by the incorporation of two cyano groups in position 2 after the thionation of the carbonyl group of lactone. With the objective to extend the delocalization of the -electron system, we have designed and synthesized new 4-styryl coumarin derivatives, with absorption and emission at long wavelengths, combined with large Stokes shifts, using a simple, low-cost and efficient synthetic strategy (Scheme 1). sensitive analytical techniques to track and detect nucleic acids, oligonucleotides, antibodies, proteins, lipids, carbohydrates, and other biomolecules. Of all sensitive analytical techniques, presents numerous advantages as it allows the use of small sample quantities as well as the respective labels [1,2]. The availability and the development of new fluorophores are now enabling previously studies of cellular processes and the detection of specific components of complex biomolecular selectivity and exquisite sensitivity, in vitro and in vivo, as well the analysis of their interactions context, due to the high cost of the available commercial fluorescent labels, coumarin derivatives to develop low-cost new fluorophores with absorption and emission at long wavelengths, combined Stokes shifts. In this work, we developed an effective synthetic strategy to produce new red-shifted coumarins using 7-diethylamino-4-methylcoumarin (1) as a starting material. These could be fluorescent labels for biomolecules. The main synthetic strategy to obtain 4-styryl coumarins high acidity of the methyl protons present at position 4 in 2-(7-(diethylamino)-4-methyl-2H-chromen-ylidene)malononitrile (3), that enable aldol condensation reactions. The mentioned dicyanomethylenecoumarinylmethyl derivative, with a higher bathochromic shift than 100 nm when compared with was obtained by the incorporation of two cyano groups in position 2 after the thionation of the the lactone. With the objective to extend the delocalization of the π-electron system, we have synthesized new 4-styryl coumarin derivatives, with absorption and emission at long wavelengths, large Stokes shifts, using a simple, low-cost and efficient synthetic strategy (Scheme 13). Scheme 13. Synthesis of the 4-styryl coumarin derivatives |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-01-01T00:00:00Z 2023-01-04T15:11:36Z 2023-01-04 |
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 |
http://hdl.handle.net/10174/33124 https://doi.org/Pereira, F.; Lourenço, A.; Aires-de-Sousa, J.; Ferreira, L.M.; Marques, M.M.B.; Sousa, E.; Branco, P.S. 14th Edition of the Nacional Organic Chemistry Meeting and 7th Edition of the Nacional Therapeutic Chemistry Meeting. Chem. Proc. 2022, 11, 1, p62. https://doi.org/10.3390/ chemproc2022011001 http://hdl.handle.net/10174/33124 https://doi.org/10.3390/ chemproc2022011001 |
url |
http://hdl.handle.net/10174/33124 https://doi.org/Pereira, F.; Lourenço, A.; Aires-de-Sousa, J.; Ferreira, L.M.; Marques, M.M.B.; Sousa, E.; Branco, P.S. 14th Edition of the Nacional Organic Chemistry Meeting and 7th Edition of the Nacional Therapeutic Chemistry Meeting. Chem. Proc. 2022, 11, 1, p62. https://doi.org/10.3390/ chemproc2022011001 https://doi.org/10.3390/ chemproc2022011001 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.none.fl_str_mv |
https://www.mdpi.com/2673-4583/11/1/1 raqueleustaquio98@hotmail.com jpcar@uevora.pt atc@uevora.pt amlp@uevora.pt 307 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
MDPI - Chemistry Proceedings |
publisher.none.fl_str_mv |
MDPI - Chemistry Proceedings |
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 |
|
_version_ |
1799136702290198528 |