title: Influence of the Headgroup of Azolium-Based Lipids on Their Biophysical Properties and Cytotoxicity.
abstract: A series of (un-)charged NHC derivatives bearing two pentadecyl chains in the backbone was studied in detail to find cooperative effects between the membrane and the NHC derivative. The tendency to show lipid-like behavior is dependent on the properties of the NHC derivative headgroup, which can be modified on demand. The surface activity was investigated by film balance measurements, epifluorescence microscopy, and differential scanning calorimetry. Additionally the cytotoxicity was evaluated against different cell lines such as eukaryotic tumor cell lines. These novel lipid-like NHC derivatives offer a broad spectrum for biological applications.
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Rühling
authors.affiliation: Westfälische Wilhelms-Universität Münster, Institut für Biochemie, Wilhelm-Klemm-Straße 2, 48149, Münster, Germany.
authors.forename: Da
authors.initials: D
authors.lastname: Wang
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Johannes B
authors.initials: JB
authors.lastname: Ernst
authors.affiliation: Westfälische Wilhelms-Universität Münster, Institut für Biochemie, Wilhelm-Klemm-Straße 2, 48149, Münster, Germany.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Wulff
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Roman
authors.initials: R
authors.lastname: Honeker
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Richter
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Angélique
authors.initials: A
authors.lastname: Ferry
authors.affiliation: Westfälische Wilhelms-Universität Münster, Institut für Biochemie, Wilhelm-Klemm-Straße 2, 48149, Münster, Germany.
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Galla
authors.affiliation: Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstrasse 40, 48149, Münster, Germany.
authors.forename: Frank
authors.identifier: http://orcid.org/0000-0002-0648-956X
authors.initials: F
authors.lastname: Glorius
mesh_terms: D015060:1,2-Dipalmitoylphosphatidylcholine / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D002152:Calorimetry, Differential Scanning; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000737:chemistry; D006801:Humans; D008055:Lipids / Q000737:chemistry*; D008081:Liposomes / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity; D008697:Methane / Q000031:analogs & derivatives / Q000737:chemistry; D008856:Microscopy, Fluorescence
chemical_list: D000970:Antineoplastic Agents; D006571:Heterocyclic Compounds; D008055:Lipids; D008081:Liposomes; C030011:carbene; D015060:1,2-Dipalmitoylphosphatidylcholine; D008697:Methane
keywords: NHC salts; antitumor reagents; cooperative effects; cytotoxicity; lipids; surface activity