Orthogonal Click Conjugation to the Liposomal Surface Reveals the Stability of the Lipid Anchorage as Crucial for Targeting
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Thomas Fritz
- Matthias Voigt
- Matthias Worm
- Inka Negwer
- Sophie S Mueller
- Kathrin Kettenbach
- Tobias L Ross
- Frank Roesch
- Kaloian Koynov
- Holger Frey
- Mark Helm
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000382921600014&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1002/chem.201602758
- eISSN
- 1521-3765
- Externe Identifier
- Clarivate Analytics Document Solution ID: DV4UU
- PubMed Identifier: 27403892
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 33
- Zeitschrift
- CHEMISTRY-A EUROPEAN JOURNAL
- Schlüsselwörter
- click chemistry
- drug delivery
- folic acid
- liposomes
- polyglycerol
- Paginierung
- 11578 - 11582
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Titel
- Orthogonal Click Conjugation to the Liposomal Surface Reveals the Stability of the Lipid Anchorage as Crucial for Targeting
- Sub types
- Article
- Ausgabe der Zeitschrift
- 22
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>Synthetic access to multiple surface decorations are a bottleneck in the development of liposomes for receptor mediated targeting. This opens a complex multiparameter space, exploration of which is severely limited in terms of sample numbers and turnaround times. Here, we unlock this technological barrier by a combination of a milligram‐scale liposome formulation using dual centrifugation and orthogonal click chemistry on the liposomal surface. Application of these techniques to conceptually new amphiphilic compounds, which feature norbornene and alkyne groups at the apex of sterically stabilizing, hyperbranched polyglycerol moieties, revealed a particular influence of the membrane anchor of functional amphiphiles. Folic acid residues clicked to cholesterol‐based amphiphiles were inefficient in folate‐mediated cell targeting, while dialkyl‐anchored amphiphiles remained stable in the liposomal membrane and imparted efficient targeting properties. These findings are of specific importance considering the popularity of cholesterol as a lipophilic anchor.</jats:p>
- Autoren
- Thomas Fritz
- Matthias Voigt
- Matthias Worm
- Inka Negwer
- Sophie S Müller
- Kathrin Kettenbach
- Tobias L Ross
- Frank Roesch
- Kaloian Koynov
- Holger Frey
- Mark Helm
- DOI
- 10.1002/chem.201602758
- eISSN
- 1521-3765
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 33
- Zeitschrift
- Chemistry – A European Journal
- Sprache
- en
- Online publication date
- 2016
- Paginierung
- 11578 - 11582
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/chem.201602758
- Datum der Datenerfassung
- 2023
- Titel
- Orthogonal Click Conjugation to the Liposomal Surface Reveals the Stability of the Lipid Anchorage as Crucial for Targeting
- Ausgabe der Zeitschrift
- 22
Datenquelle: Crossref
- Abstract
- Synthetic access to multiple surface decorations are a bottleneck in the development of liposomes for receptor mediated targeting. This opens a complex multiparameter space, exploration of which is severely limited in terms of sample numbers and turnaround times. Here, we unlock this technological barrier by a combination of a milligram-scale liposome formulation using dual centrifugation and orthogonal click chemistry on the liposomal surface. Application of these techniques to conceptually new amphiphilic compounds, which feature norbornene and alkyne groups at the apex of sterically stabilizing, hyperbranched polyglycerol moieties, revealed a particular influence of the membrane anchor of functional amphiphiles. Folic acid residues clicked to cholesterol-based amphiphiles were inefficient in folate-mediated cell targeting, while dialkyl-anchored amphiphiles remained stable in the liposomal membrane and imparted efficient targeting properties. These findings are of specific importance considering the popularity of cholesterol as a lipophilic anchor.
- Addresses
- Institute of Pharmacy and Biochemistry, Johannes Gutenberg-University Mainz, Staudingerweg 5, 55128, Mainz, Germany.
- Autoren
- Thomas Fritz
- Matthias Voigt
- Matthias Worm
- Inka Negwer
- Sophie S Müller
- Kathrin Kettenbach
- Tobias L Ross
- Frank Roesch
- Kaloian Koynov
- Holger Frey
- Mark Helm
- DOI
- 10.1002/chem.201602758
- eISSN
- 1521-3765
- Externe Identifier
- PubMed Identifier: 27403892
- Funding acknowledgements
- DFG: SFB1066
- Open access
- false
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 33
- Zeitschrift
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Schlüsselwörter
- Humans
- Glycerol
- Folic Acid
- Cholesterol
- Polymers
- Lipids
- Liposomes
- Click Chemistry
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2016
- Paginierung
- 11578 - 11582
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum der Datenerfassung
- 2016
- Titel
- Orthogonal Click Conjugation to the Liposomal Surface Reveals the Stability of the Lipid Anchorage as Crucial for Targeting.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 22
Datenquelle: Europe PubMed Central
- Abstract
- Synthetic access to multiple surface decorations are a bottleneck in the development of liposomes for receptor mediated targeting. This opens a complex multiparameter space, exploration of which is severely limited in terms of sample numbers and turnaround times. Here, we unlock this technological barrier by a combination of a milligram-scale liposome formulation using dual centrifugation and orthogonal click chemistry on the liposomal surface. Application of these techniques to conceptually new amphiphilic compounds, which feature norbornene and alkyne groups at the apex of sterically stabilizing, hyperbranched polyglycerol moieties, revealed a particular influence of the membrane anchor of functional amphiphiles. Folic acid residues clicked to cholesterol-based amphiphiles were inefficient in folate-mediated cell targeting, while dialkyl-anchored amphiphiles remained stable in the liposomal membrane and imparted efficient targeting properties. These findings are of specific importance considering the popularity of cholesterol as a lipophilic anchor.
- Autoren
- Thomas Fritz
- Matthias Voigt
- Matthias Worm
- Inka Negwer
- Sophie S Müller
- Kathrin Kettenbach
- Tobias L Ross
- Frank Roesch
- Kaloian Koynov
- Holger Frey
- Mark Helm
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/27403892
- DOI
- 10.1002/chem.201602758
- eISSN
- 1521-3765
- Ausgabe der Veröffentlichung
- 33
- Zeitschrift
- Chemistry
- Schlüsselwörter
- click chemistry
- drug delivery
- folic acid
- liposomes
- polyglycerol
- Cholesterol
- Click Chemistry
- Folic Acid
- Glycerol
- Humans
- Lipids
- Liposomes
- Polymers
- Sprache
- eng
- Country
- Germany
- Paginierung
- 11578 - 11582
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2018
- Titel
- Orthogonal Click Conjugation to the Liposomal Surface Reveals the Stability of the Lipid Anchorage as Crucial for Targeting.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 22
Datenquelle: PubMed
- Beziehungen:
- Eigentum von