UAM_Biblioteca | Unified search engine | Scientific Production Portal | UAM Research Data Repository
Universidad Autónoma de Madrid
Biblos-e Archivo
We are onFacebookCanal BiblosYouTubeTwitterPinterestWhatsappInstagram
    • español
    • English
  • English 
    • español
    • English
  • Log in
JavaScript is disabled for your browser. Some features of this site may not work without it.

Search Biblos-e Archivo

Advanced Search

Browse

All of Biblos-e ArchivoCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsFacultiesThis CollectionBy Issue DateAuthorsTitlesSubjectsFaculties

My Account

Log inRegister

Statistics

View Usage Statistics

Help

Information about Biblos-e ArchivoI want to submit my workI want to submit my doctoral thesisFrequently Asked QuestionsCopyrightsFinancial Agencies and OA policy

UAM_Biblioteca

View Item 
  •   Biblos-e Archivo
  • 1 - Producción científica en acceso abierto de la UAM
  • Producción científica en acceso abierto de la UAM
  • View Item
  •   Biblos-e Archivo
  • 1 - Producción científica en acceso abierto de la UAM
  • Producción científica en acceso abierto de la UAM
  • View Item

Turn-on Fluorescent Biosensors for Imaging Hypoxia-like Conditions in Living Cells

Author
Guisán Ceinos, Santiagountranslated; Rivero, Alexandra R.; Romeo Gella, Fernandountranslated; Simón Fuente, Silvia; Gómez Pastor, Silvia; Calvo, Natalia; Orrego, Alejandro H.; Guisán, José Manuel; Corral Pérez, Inésuntranslated; Sanz Rodríguez, Franciscountranslated; Ribagorda Lobera, Maríauntranslated
Entity
UAM. Departamento de Biología; UAM. Departamento de Química; UAM. Departamento de Química Orgánica
Publisher
American Chemical Society
Date
2022-04-29
Citation
10.1021/jacs.2c01197
Journal of the American Chemical Society 144.18 (2022): 8185–8193
 
 
 
ISSN
0002-7863 (print); 1520-5126 (online)
DOI
10.1021/jacs.2c01197
Funded by
This article is dedicated to Professor M. Carmen Carreño on the occasion of her retirement. We thank MINECO (grant CTQ2017-85454-C2-2-P), MICINN (grant PID2020- 113059GB-C22), MCIU (grant PGC2018-094644-B-C21), the Ramón y Cajal Program (grant RYC-2016-20489), the Fundación La Caixa (grant no. LCF/BQ/DR19/11740024), and the Comunidad Autónoma de Madrid (B2017/BMD-3867 RENIMCM) and co-financed by the European Structural and investment fund for financial support. I.C. and F.R.-G. also acknowledge the Red Española de Supercomputación, the MareNostrum Supercomputer Center, and the Centro de Computación Científica of the UAM (CCC-UAM) for the generous allocation of computer time and for their technical support. We thank the “Servicio de Microscopía óptica y confocal CBMSO” facility for their assistance. We also thank Prof. M. C. Carreño for her advice and helpful discussions during the work
Project
Gobierno de España. CTQ2017-85454-C2-2-P; Gobierno de España. PID2020-113059GB-C22
Editor's Version
https://doi.org/10.1021/jacs.2c01197
Subjects
Biología y Biomedicina / Biología; Química
URI
http://hdl.handle.net/10486/703655
Rights
© 2022 The Authors

Licencia Creative Commons
Esta obra está bajo una Licencia Creative Commons Atribución 4.0 Internacional.

Abstract

We present the synthesis, photophysical properties, and biological application of nontoxic 3-azo-conjugated BODIPY dyes as masked fluorescent biosensors of hypoxia-like conditions. The synthetic methodology is based on an operationally simple N=N bond-forming protocol, followed by a Suzuki coupling, that allows for a direct access to simple and underexplored 3-azo-substituted BODIPY. These dyes can turn on their emission properties under both chemical and biological reductive conditions, including bacterial and human azoreductases, which trigger the azo bond cleavage, leading to fluorescent 3-amino-BODIPY. We have also developed a practical enzymatic protocol, using an immobilized bacterial azoreductase that allows for the evaluation of these azo-based probes and can be used as a model for the less accessible and expensive human reductase NQO1. Quantum mechanical calculations uncover the restructuration of the topography of the S1 potential energy surface following the reduction of the azo moiety and rationalize the fluorescent quenching event through the mapping of an unprecedented pathway. Fluorescent microscopy experiments show that these azos can be used to visualize hypoxia-like conditions within living cells
Show full item record

Files in this item

Thumbnail
Name
fluorescent_guisan_j_am_chem_soc_2022.pdf
Size
4.576Mb
Format
PDF
Description
Artículo

Refworks Export

Delicious Save this on Delicious

Google™ Scholar:Guisán Ceinos, Santiago - Rivero, Alexandra R. - Romeo Gella, Fernando - Simón Fuente, Silvia - Gómez Pastor, Silvia - Calvo, Natalia - Orrego, Alejandro H. - Guisán, José Manuel - Corral Pérez, Inés - Sanz Rodríguez, Francisco - Ribagorda Lobera, María

This item appears in the following Collection(s)

  • Producción científica en acceso abierto de la UAM [15094]

Related items

Showing items related by title, author, creator and subject.

  • Aldehydes as photoremovable directing groups: synthesis of pyrazoles by a photocatalyzed [3+2] cycloaddition/norrish type fragmentation sequence 

    Pascual-Escudero, Ana; Ortiz-Rojano, Laura; Simón-Fuente, Silvia; Adrio Sevilla, Francisco JavierAutoridad UAM; Ribagorda, María
    2021-06-07
  • Acceptability and feasibility of a virtual community of practice to primary care professionals regarding patient empowerment: A qualitative pilot study 

    Bermejo-Caja, Carlos Jesús; Koatz, Débora; Orrego, Carola; Perestelo-Pérez, Lilisbeth; González-González, Ana Isabel; Ballester, Marta; Pacheco-Huergo, Valeria; Del Rey-Granado, Yolanda; Muñoz-Balsa, Marcos; Ramírez-Puerta, Ana Belén; Canellas-Criado, Yolanda; Pérez-Rivas, Francisco Javier; Toledo-Chávarri, Ana; Martínez-Marcos, Mercedes; Alejo-Díaz-Zorita, Concepción; Barbero-Macías, Cynthia A.; Borrell-Punzón, Fernando; Bueno-Rodriguez, Beatriz; Colmena-Martin, Begoña; Del Valle-De Joz, Isabel; Gamboa-Puñal, Juan Carlos; García-Valverde, Concepción; Gómez-Garzón, Luis Miguel; Gómez-López, Arturo; Hernaz-Guijo, Alejandro; Herrera-León, Walter Nery; Iniesta-González, Irene; Leza-Leza, Margarita; Melchor-Canelo, María Aranzazu; Muñoz-Quirós-Aliaga, Sagrario; Oria-Fernández, Ángela; Pertierra-Galindo, Nuria; Prieto-Barbosa, M. Dolores; Robledo-Vázquez, Milagros; Ruiz-López, Marta; Sánchez-Cruz, M. Carmen; Sánchez-De-Eusebio, M. Ángeles; Seijas-Martínez-Echevarría, M. Jose; Tovar-García, Carmen Paola; Vicente-Diez, Jose Ignacio; Villanueva-Sanz, Cristina
    2019-06-20
  • Copper-catalyzed diastereo- and enantioselective desymmetrization of cyclopropenes: Synthesis of cyclopropylboronates 

    Parra, Alejandro; Amenós, Laura; Guisán-Ceinos, Manuel; López, Aurora; García Ruano, José Luis; Tortosa Manzanares, MariolaAutoridad UAM
    2014-11-12
All the documents from Biblos-e Archivo are protected by copyrights. Some rights reserved.
Universidad Autónoma de Madrid. Biblioteca
Contact Us | Send Feedback
We are onFacebookCanal BiblosYouTubeTwitterPinterestWhatsappInstagram
 

 

All the documents from Biblos-e Archivo are protected by copyrights. Some rights reserved.
Universidad Autónoma de Madrid. Biblioteca
Contact Us | Send Feedback
We are onFacebookCanal BiblosYouTubeTwitterPinterestWhatsappInstagram