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

Xueshu Li, Jaroslav Turánek, Pavlína Knötigová, Hana Kudláčková, Josef Mašek, Sean Parkin, Stephen E. Rankin, Barbara L. Knutson, Hans Joachim Lehmler

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

A series of hydrocarbon and fluorocarbon carbohydrate surfactants with different headgroups (i.e., gluco-, galacto- and maltopyranoside) and (fluorinated) alkyl tails (i.e., C7 and C14 to C19) was synthesized to investigate trends in their cytotoxicity and haemolytic activity, and how surfactant-lipid interactions of selected surfactants contribute to these two measures of biocompatibility. All surfactants displayed low cytotoxicity (EC50 = 25 to >250 μM) and low haemolytic activity (EC50 = 0.2 to >3.3 mM), with headgroup structure, tail length and degree of fluorination being important structural determinants for both endpoints. The EC50 values of hydrocarbon and fluorocarbon glucopyranoside surfactants displayed a "cut-off" effect (i.e., a maximum with respect to the chain length). According to steady-state fluorescence anisotropy studies, short chain (C7) surfactants partitioned less readily into model membranes, which explains their low cytotoxicity and haemolytic activity. Interestingly, galactopyranosides were less toxic compared to glucopyranosides with the same hydrophobic tail. Although both surfactant types only differ in the stereochemistry of the 4-OH group, hexadecyl gluco- and galactopyranoside surfactants had similar apparent membrane partition coefficients, but differed in their overall effect on the phase behaviour of DPPC model membranes, as assessed using steady-state fluorescence anisotropy studies. These observations suggest that highly selective surfactant-lipid interactions may be responsible for the differential cytotoxicity and, possible, haemolytic activity of hydrocarbon and fluorocarbon carbohydrate surfactants intended for a variety of pharmaceutical and biomedical applications.

Original languageEnglish
Pages (from-to)65-74
Number of pages10
JournalColloids and Surfaces B: Biointerfaces
Volume73
Issue number1
DOIs
StatePublished - Oct 1 2009

Bibliographical note

Funding Information:
This work was supported by grants from the National Institute of Environmental Health Sciences (ES12475), the National Science Foundation (NIRT 0210517), the U.S. Department of Agriculture Biomass Research and Development Initiative (Grant Agreement 68-3A75-7-608) and the Department of Energy Development and Independence, Energy and Environment Cabinet of The Commonwealth of Kentucky. Additional support was provided by grants from the Ministry of Agriculture of the Czech Republic (grant No. MZE-0002716202) and NAZV QF-3115 to JT. Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the funding agencies.

Keywords

  • Cytotoxicity
  • DPPC
  • Fluorescence anisotropy
  • Haemolytic activity
  • Surfactant-lipid interactions

ASJC Scopus subject areas

  • Biotechnology
  • Surfaces and Interfaces
  • Physical and Theoretical Chemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Hydrophobic tail length, degree of fluorination and headgroup stereochemistry are determinants of the biocompatibility of (fluorinated) carbohydrate surfactants'. Together they form a unique fingerprint.

Cite this