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Synthetic Macrocyclic Peptidomimetics as Tunable pH Probes for the Fluorescence Imaging of Acidic Organelles in Live Cells

2005; Wiley; Volume: 44; Issue: 40 Linguagem: Inglês

10.1002/anie.200501920

1521-3773

Francisco Galindo, M. Isabel Burguete, Laura Vigara, Santiago V. Luis, Nurul Kabir, Jelena Gavrilović, David A. Russell,

Luminescence and Fluorescent Materials

Angewandte Chemie International EditionVolume 44, Issue 40 p. 6504-6508 Communication Synthetic Macrocyclic Peptidomimetics as Tunable pH Probes for the Fluorescence Imaging of Acidic Organelles in Live Cells† Francisco Galindo Dr., Francisco Galindo Dr. francisco.galindo@qio.uji.es Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorM. Isabel Burguete Dr., M. Isabel Burguete Dr. Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorLaura Vigara, Laura Vigara Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorSantiago V. Luis Prof. Dr., Santiago V. Luis Prof. Dr. luiss@qio.uji.es Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorNurul Kabir Dr., Nurul Kabir Dr. School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK, Fax: (+44) 1603-593-012 School of Biological Sciences, University of East Anglia, Norwich, Norfolk NR4 7TJ, UKSearch for more papers by this authorJelena Gavrilovic Prof. Dr., Jelena Gavrilovic Prof. Dr. School of Biological Sciences, University of East Anglia, Norwich, Norfolk NR4 7TJ, UKSearch for more papers by this authorDavid A. Russell Prof. Dr., David A. Russell Prof. Dr. d.russell@uea.ac.uk School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK, Fax: (+44) 1603-593-012Search for more papers by this author Francisco Galindo Dr., Francisco Galindo Dr. francisco.galindo@qio.uji.es Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorM. Isabel Burguete Dr., M. Isabel Burguete Dr. Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorLaura Vigara, Laura Vigara Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorSantiago V. Luis Prof. Dr., Santiago V. Luis Prof. Dr. luiss@qio.uji.es Departamento de Química Inorgánica y Orgánica, Universitat Jaume I, Avda. Sos Baynat, s/n, 12071 Castellón, Spain, Fax: (+34) 964-72-8214Search for more papers by this authorNurul Kabir Dr., Nurul Kabir Dr. School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK, Fax: (+44) 1603-593-012 School of Biological Sciences, University of East Anglia, Norwich, Norfolk NR4 7TJ, UKSearch for more papers by this authorJelena Gavrilovic Prof. Dr., Jelena Gavrilovic Prof. Dr. School of Biological Sciences, University of East Anglia, Norwich, Norfolk NR4 7TJ, UKSearch for more papers by this authorDavid A. Russell Prof. Dr., David A. Russell Prof. Dr. d.russell@uea.ac.uk School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich, Norfolk NR4 7TJ, UK, Fax: (+44) 1603-593-012Search for more papers by this author First published: 07 October 2005 https://doi.org/10.1002/anie.200501920Citations: 143 † This work was supported by the Spanish Ministerio de Ciencia y Tecnología (Project BQU-2003-0915-C03-02), Fundació Caixa Castelló-Bancaixa and Universitat Jaume I (Project 04I007.25/1 to F.G.), and The Wellcome Trust (Showcase award to D.A.R. and J.G.). F.G. thanks the Spanish MEC for financial support (Ramón y Cajal Program). Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Acid test: Macrocyclic compounds that comprise a 9,10-anthracene subunit linked by a C2-symmetric peptidomimetic chain (see formula) are useful as fluorescent probes in a pH range of biomedical interest. Changes in the size of the macrocycle (n=3,4,6,8) produce a shift in the pKa values. Experiments with live mouse macrophage cells show the selective localization of the probe in the acidic organelles (see differential interference contrast image). Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z501920_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume44, Issue40October 14, 2005Pages 6504-6508 RelatedInformation