Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents

Detalhes bibliográficos
Autor(a) principal: Pereira, Nelson A. M.
Data de Publicação: 2017
Outros Autores: Laranjo, Mafalda, Casalta-Lopes, João, Serra, Arménio C., Piñeiro, Marta, Pina, João, Seixas de Melo, J. Sérgio, Senge, Mathias O., Botelho, M. Filomena, Martelo, Liliana, Burrows, Hugh D., Pinho e Melo, Teresa M. V. D.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/41710
https://doi.org/10.1021/acsmedchemlett.6b00476
Resumo: Novel near-infrared luminescent compounds based on platinum(II) 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused chlorins are described. These compounds have high photostability and display light emission, in particular simultaneous fluorescence and phosphorescence emission in solution at room temperature, in the biologically relevant 700-850 nm red and near-infrared (NIR) spectral region, making them excellent materials for biological imaging. The simultaneous presence of fluorescence and phosphorescence emission at room temperature, with the phosphorescence strongly quenched by oxygen whereas fluorescence remains unaffected, allows these compounds to be used as ratiometric oxygen sensors in chemical and biological media. Both steady-state (fluorescence vs phosphorescence intensities) and dynamic (dependence of phosphorescence lifetimes upon oxygen concentration) luminescence approaches can be used. Photocytotoxicity studies against human melanocytic melanoma cells (A375) indicate that these compounds display potential as photosensitizers in photodynamic therapy.
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spelling Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic AgentsNovel near-infrared luminescent compounds based on platinum(II) 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused chlorins are described. These compounds have high photostability and display light emission, in particular simultaneous fluorescence and phosphorescence emission in solution at room temperature, in the biologically relevant 700-850 nm red and near-infrared (NIR) spectral region, making them excellent materials for biological imaging. The simultaneous presence of fluorescence and phosphorescence emission at room temperature, with the phosphorescence strongly quenched by oxygen whereas fluorescence remains unaffected, allows these compounds to be used as ratiometric oxygen sensors in chemical and biological media. Both steady-state (fluorescence vs phosphorescence intensities) and dynamic (dependence of phosphorescence lifetimes upon oxygen concentration) luminescence approaches can be used. Photocytotoxicity studies against human melanocytic melanoma cells (A375) indicate that these compounds display potential as photosensitizers in photodynamic therapy.This work was funded by FEDER - Fundo Europeu de Desenvolvimento Regional through the COMPETE 2020 - Operational Programme for Competitiveness and Internationalisation (POCI), and by Portuguese funds through FCT - Fundação para a Ciência e a Tecnologia in the framework of the project POCI-01-0145-FEDER-PTDC/QEQ- MED/0262/2014.), Portuguese Agency for Scientific Research. The Coimbra Chemistry Centre (CQC) is supported by FCT through project no 007630 UID/QUI/00313/2013, co-funded by COMPETE2020-UE. The FCT is also acknowledged for a post-doctoral grant to J. Pina (ref. SFRH/BPD/108469/2015). We acknowledge the UC-NMR facility for obtaining the NMR data (www.nmrccc.uc.pt), and Professor Mário N. Berberan- Santos (Instituto Superior Técnico) for valuable discussions The authors also gratefully acknowledge Perkin-Helmer, Inc. and Intrumentos de Laboratório Científico, Lda (ILC) for providing the EnSpire Multimode Plate Reader and Dr. Hans-Peter Steffens (Perkin-Helmer, Inc) for technical support. MOS acknowledges grant SFI IvP 13/1894.2017info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/41710http://hdl.handle.net/10316/41710https://doi.org/10.1021/acsmedchemlett.6b00476engPereira, Nelson A. M.Laranjo, MafaldaCasalta-Lopes, JoãoSerra, Arménio C.Piñeiro, MartaPina, JoãoSeixas de Melo, J. SérgioSenge, Mathias O.Botelho, M. FilomenaMartelo, LilianaBurrows, Hugh D.Pinho e Melo, Teresa M. V. D.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:RCAAP2023-04-06T10:19:53Zoai:estudogeral.uc.pt:10316/41710Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:51.005567Repositório 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 Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
title Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
spellingShingle Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
Pereira, Nelson A. M.
title_short Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
title_full Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
title_fullStr Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
title_full_unstemmed Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
title_sort Platinum(II) Ring-Fused Chlorins as Near-Infrared Emitting Oxygen Sensors and Photodynamic Agents
author Pereira, Nelson A. M.
author_facet Pereira, Nelson A. M.
Laranjo, Mafalda
Casalta-Lopes, João
Serra, Arménio C.
Piñeiro, Marta
Pina, João
Seixas de Melo, J. Sérgio
Senge, Mathias O.
Botelho, M. Filomena
Martelo, Liliana
Burrows, Hugh D.
Pinho e Melo, Teresa M. V. D.
author_role author
author2 Laranjo, Mafalda
Casalta-Lopes, João
Serra, Arménio C.
Piñeiro, Marta
Pina, João
Seixas de Melo, J. Sérgio
Senge, Mathias O.
Botelho, M. Filomena
Martelo, Liliana
Burrows, Hugh D.
Pinho e Melo, Teresa M. V. D.
author2_role author
author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Pereira, Nelson A. M.
Laranjo, Mafalda
Casalta-Lopes, João
Serra, Arménio C.
Piñeiro, Marta
Pina, João
Seixas de Melo, J. Sérgio
Senge, Mathias O.
Botelho, M. Filomena
Martelo, Liliana
Burrows, Hugh D.
Pinho e Melo, Teresa M. V. D.
description Novel near-infrared luminescent compounds based on platinum(II) 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine-fused chlorins are described. These compounds have high photostability and display light emission, in particular simultaneous fluorescence and phosphorescence emission in solution at room temperature, in the biologically relevant 700-850 nm red and near-infrared (NIR) spectral region, making them excellent materials for biological imaging. The simultaneous presence of fluorescence and phosphorescence emission at room temperature, with the phosphorescence strongly quenched by oxygen whereas fluorescence remains unaffected, allows these compounds to be used as ratiometric oxygen sensors in chemical and biological media. Both steady-state (fluorescence vs phosphorescence intensities) and dynamic (dependence of phosphorescence lifetimes upon oxygen concentration) luminescence approaches can be used. Photocytotoxicity studies against human melanocytic melanoma cells (A375) indicate that these compounds display potential as photosensitizers in photodynamic therapy.
publishDate 2017
dc.date.none.fl_str_mv 2017
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dc.identifier.uri.fl_str_mv http://hdl.handle.net/10316/41710
http://hdl.handle.net/10316/41710
https://doi.org/10.1021/acsmedchemlett.6b00476
url http://hdl.handle.net/10316/41710
https://doi.org/10.1021/acsmedchemlett.6b00476
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