A Remarkably Simple Class of Imidazolium-Based Lipids and Their Biological Properties.
A series of imidazolium salts bearing two alkyl chains in the backbone of the imidazolium core were synthesized, resembling the structure of lipids. Their antibacterial activity and cytotoxicity were evaluated using Gram-positive and Gram-negative bacteria and eukaryotic cell lines including tumor cells. It is shown that the length of alkyl chains in the backbone is vital for the antibiofilm activities of these lipid-mimicking components. In addition to their biological activity, their surface activity and their membrane interactions are shown by film balance and quartz crystal microbalance (QCM) measurements. The structure-activity relationship indicates that the distinctive chemical structure contributes considerably to the biological activities of this novel class of lipids.
Institut für Biochemie, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Straße 2, 48149 Münster (Germany).
Da
D
Wang
Organisch Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany).
Christian
C
Richter
Organisch Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany).
Andreas
A
Rühling
Institut für Biochemie, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Straße 2, 48149 Münster (Germany).
Patrick
P
Drücker
Institut für Bioinorganische Chemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum (Germany).
Daniel
D
Siegmund
Institut für Bioinorganische Chemie, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum (Germany).
Nils
N
Metzler-Nolte
Organisch Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany). glorius@uni-muenster.de.
Frank
F
Glorius
Institut für Biochemie, Westfälische Wilhelms-Universität Münster, Wilhelm-Klemm-Straße 2, 48149 Münster (Germany). gallah@uni-muenster.de.
Hans-Joachim
HJ
Galla
D000473:Alkanes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000633:toxicity; D001686:Biological Phenomena; D045744:Cell Line, Tumor; D006090:Gram-Negative Bacteria / Q000737:chemistry / Q000187:drug effects*; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008055:Lipids / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D012492:Salts / Q000737:chemistry; D013329:Structure-Activity Relationship
D000473:Alkanes; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D007093:Imidazoles; D008055:Lipids; D000644:Quaternary Ammonium Compounds; D012492:Salts
NHC salts; antitumor agents; cytotoxicity; lipids; surface activity