An Amphotericin B–Fluorescein Conjugate as a Powerful Probe for Biochemical Studies of the Membrane†
Andreas Zumbuehl
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI H335, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorDamien Jeannerat Dr.
Départment de Chimie Organique, Université de Genève, 1211 Genève 4, Switzerland
Search for more papers by this authorScott E. Martin Dr.
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorMarc Sohrmann Dr.
Institut für Biochemie, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorPasquale Stano
Department of Chemistry, The Pennsylvania State University, Pennsylvania 16802, USA
Search for more papers by this authorTamas Vigassy Dr.
Laboratorium für Organische Chemie, ETH-Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorDaniel D. Clark
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorStephen L. Hussey Dr.
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorMathias Peter Prof. Dr.
Institut für Biochemie, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorBlake R. Peterson Prof. Dr.
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorErnö Pretsch Prof. Dr.
Laboratorium für Organische Chemie, ETH-Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorPeter Walde Prof. Dr.
Department of Chemistry, The Pennsylvania State University, Pennsylvania 16802, USA
Search for more papers by this authorErick M. Carreira Prof. Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI H335, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorAndreas Zumbuehl
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI H335, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorDamien Jeannerat Dr.
Départment de Chimie Organique, Université de Genève, 1211 Genève 4, Switzerland
Search for more papers by this authorScott E. Martin Dr.
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorMarc Sohrmann Dr.
Institut für Biochemie, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorPasquale Stano
Department of Chemistry, The Pennsylvania State University, Pennsylvania 16802, USA
Search for more papers by this authorTamas Vigassy Dr.
Laboratorium für Organische Chemie, ETH-Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorDaniel D. Clark
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorStephen L. Hussey Dr.
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorMathias Peter Prof. Dr.
Institut für Biochemie, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorBlake R. Peterson Prof. Dr.
Departement Materialwissenschaft, ETH Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorErnö Pretsch Prof. Dr.
Laboratorium für Organische Chemie, ETH-Hönggerberg, 8093 Zürich, Switzerland
Search for more papers by this authorPeter Walde Prof. Dr.
Department of Chemistry, The Pennsylvania State University, Pennsylvania 16802, USA
Search for more papers by this authorErick M. Carreira Prof. Dr.
Laboratorium für Organische Chemie, ETH Hönggerberg, HCI H335, 8093 Zürich, Switzerland, Fax: (+41) 1-632-1328
Search for more papers by this authorWe would like to thank Prof. Dr. Josef Brunner for helpful discussions. E.M.C. is grateful for generous support from the Eidgenössische Technische Hochschule (ETH), Zürich (TH-Gesuch) and from F. Hoffmann LaRoche. B.R.P. acknowledges support from the National Institutes of Health, USA (Grant no. RO1-CA83831).
Graphical Abstract
Not only skin deep: A fluorescein–amphotericin B conjugate with a new piperazine linker (see structure) was prepared and used as a probe of the biomembrane and the mechanism of action of amphotericin B both in vivo and in liposomal experiments. The amphotericin B analogue localizes at the membrane of yeast cells but is internalized by mammalian cells.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2004/z460489_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.
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