Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Benedict Kemper
- Maximilian von Groening
- Vanessa Lewe
- Daniel Spitzer
- Tobias Otremba
- Natascha Stergiou
- Dieter Schollmeyer
- Edgar Schmitt
- Bart Jan Ravoo
- Pol Besenius
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000400580000031&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1002/chem.201700588
- eISSN
- 1521-3765
- Externe Identifier
- Clarivate Analytics Document Solution ID: ET8UZ
- PubMed Identifier: 28181714
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 25
- Zeitschrift
- CHEMISTRY-A EUROPEAN JOURNAL
- Schlüsselwörter
- click chemistry
- Diels-Alder ligation
- gold
- metalloamphiphiles
- self-assembly
- Paginierung
- 6048 - 6055
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Titel
- Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes
- Sub types
- Article
- Proceedings Paper
- Ausgabe der Zeitschrift
- 23
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water‐soluble Au<jats:sup>I</jats:sup>‐<jats:italic>N</jats:italic>‐alkynyl substituted maleimide complexes. For this purpose, two different polar ligands were applied: 1) a neutral, dendritic tetraethylene glycol‐functionalized phosphane and 2) a charged, sulfonated N‐heterocyclic carbene (NHC). The retro Diels–Alder reaction of a furan‐protected maleimide gold(I) complex, followed by cycloaddition with a diene‐functionalized biotin under mild conditions leads to a novel gold(I) metalloamphiphile. The strong streptavidin–biotin binding affinity in buffered aqueous solution of the resulting biotin alkynyl gold(I) phosphane conjugate remains intact. The cytotoxicity of the biotinylated gold(I) complex against a T47D human breast cancer cell line is higher than for cisplatin.</jats:p>
- Autoren
- Benedict Kemper
- Maximilian von Gröning
- Vanessa Lewe
- Daniel Spitzer
- Tobias Otremba
- Natascha Stergiou
- Dieter Schollmeyer
- Edgar Schmitt
- Bart Jan Ravoo
- Pol Besenius
- DOI
- 10.1002/chem.201700588
- eISSN
- 1521-3765
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 25
- Zeitschrift
- Chemistry – A European Journal
- Sprache
- en
- Online publication date
- 2017
- Paginierung
- 6048 - 6055
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/chem.201700588
- Datum der Datenerfassung
- 2023
- Titel
- Reversible Covalent and Supramolecular Functionalization of Water‐Soluble Gold(I) Complexes
- Ausgabe der Zeitschrift
- 23
Datenquelle: Crossref
- Abstract
- The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water-soluble Au<sup>I</sup> -N-alkynyl substituted maleimide complexes. For this purpose, two different polar ligands were applied: 1) a neutral, dendritic tetraethylene glycol-functionalized phosphane and 2) a charged, sulfonated N-heterocyclic carbene (NHC). The retro Diels-Alder reaction of a furan-protected maleimide gold(I) complex, followed by cycloaddition with a diene-functionalized biotin under mild conditions leads to a novel gold(I) metalloamphiphile. The strong streptavidin-biotin binding affinity in buffered aqueous solution of the resulting biotin alkynyl gold(I) phosphane conjugate remains intact. The cytotoxicity of the biotinylated gold(I) complex against a T47D human breast cancer cell line is higher than for cisplatin.
- Addresses
- Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
- Autoren
- Benedict Kemper
- Maximilian von Gröning
- Vanessa Lewe
- Daniel Spitzer
- Tobias Otremba
- Natascha Stergiou
- Dieter Schollmeyer
- Edgar Schmitt
- Bart Jan Ravoo
- Pol Besenius
- DOI
- 10.1002/chem.201700588
- eISSN
- 1521-3765
- Externe Identifier
- PubMed Identifier: 28181714
- Funding acknowledgements
- Deutsche Forschungsgemeinschaft: SFB 858
- Deutsche Forschungsgemeinschaft: SFB 1066
- Deutsche Forschungsgemeinschaft: GSC 266
- Open access
- false
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 25
- Zeitschrift
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2017
- Paginierung
- 6048 - 6055
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Datum der Datenerfassung
- 2017
- Titel
- Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 23
Datenquelle: Europe PubMed Central
- Abstract
- The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water-soluble AuI -N-alkynyl substituted maleimide complexes. For this purpose, two different polar ligands were applied: 1) a neutral, dendritic tetraethylene glycol-functionalized phosphane and 2) a charged, sulfonated N-heterocyclic carbene (NHC). The retro Diels-Alder reaction of a furan-protected maleimide gold(I) complex, followed by cycloaddition with a diene-functionalized biotin under mild conditions leads to a novel gold(I) metalloamphiphile. The strong streptavidin-biotin binding affinity in buffered aqueous solution of the resulting biotin alkynyl gold(I) phosphane conjugate remains intact. The cytotoxicity of the biotinylated gold(I) complex against a T47D human breast cancer cell line is higher than for cisplatin.
- Autoren
- Benedict Kemper
- Maximilian von Gröning
- Vanessa Lewe
- Daniel Spitzer
- Tobias Otremba
- Natascha Stergiou
- Dieter Schollmeyer
- Edgar Schmitt
- Bart Jan Ravoo
- Pol Besenius
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/28181714
- DOI
- 10.1002/chem.201700588
- eISSN
- 1521-3765
- Ausgabe der Veröffentlichung
- 25
- Zeitschrift
- Chemistry
- Schlüsselwörter
- Diels-Alder ligation
- click chemistry
- gold
- metalloamphiphiles
- self-assembly
- Sprache
- eng
- Country
- Germany
- Paginierung
- 6048 - 6055
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2018
- Titel
- Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 23
Datenquelle: PubMed
- Beziehungen:
-