Hydrophobic tail length, degree of fluorination and headgroup stereochemistry are determinants of the biocompatibility of (fluorinated) carbohydrate surfactants

• Published in: Colloids and surfaces, B, Biointerfaces Vol. 73; no. 1; pp. 65 - 74
• Main Authors: Li, Xueshu, Turánek, Jaroslav, Knötigová, Pavlína, Kudláčková, Hana, Mašek, Josef, Parkin, Sean, Rankin, Stephen E., Knutson, Barbara L., Lehmler, Hans-Joachim
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01.10.2009
• Subjects: 1,2-Dipalmitoylphosphatidylcholine - chemistry; Animals; Biocompatible Materials - chemistry; Biocompatible Materials - pharmacology; Carbohydrates - chemistry; Cell Line, Tumor; Cell Survival - drug effects; Crystallization; Cytotoxicity; Dose-Response Relationship, Drug; DPPC; Fluorescence anisotropy; Fluorescence Polarization; Fluorocarbons - chemistry; Glucosides - chemistry; Haemolytic activity; Halogenation; Hemolysis - drug effects; Hydrophobic and Hydrophilic Interactions; Lipid Bilayers - chemistry; Membrane Fluidity - drug effects; Molecular Structure; Rabbits; Stereoisomerism; Structure-Activity Relationship; Surface-Active Agents - chemistry; Surface-Active Agents - pharmacology; Surfactant–lipid interactions; Cytotoxicity; Surfactant–lipid interactions; Fluorescence anisotropy; Haemolytic activity; DPPC

A series of hydrocarbon and fluorocarbon carbohydrate surfactants with different headgroups (i.e., gluco-, galacto- and maltopyranoside) and (fluorinated) alkyl tails (i.e., C 7 and C 14 to C 19) was synthesized to investigate trends in their cytotoxicity and haemolytic activity, and how surfactant–...