Issue 12, 2008
From the journal:

New Journal of Chemistry

Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants†

Xueshu Li,a   Jaroslav Turánek,*b   Pavlína Knötigová,b   Hana Kudláčková,b   Josef Mašek,b   D. Brant Pennington,c   Stephen E. Rankin,c   Barbara L. Knutsonc  and  Hans-Joachim Lehmler*a  

* Corresponding authors

a Department of Occupational and Environmental Health, University of Iowa, Iowa City, USA
E-mail: hans-joachim-lehmler@uiowa.edu
Fax: 3193354290
Tel: 3193354211

b Veterinary Research Institute v.v.i., Department of Vaccinology and Immunotherapy, Brno, Czech Republic
E-mail: turanek@vri.cz

c Chemicals and Materials Engineering Department, University of Kentucky, Lexington, USA

Abstract

Partially fluorinated non-ionic surfactants are of interest for a range of biomedical applications, such as the pulmonary administration of drugs using reverse water-in-perfluorocarbon microemulsions. We herein report the synthesis and characterization of a series of partially fluorinated β-D-glucopyranoside surfactants from the respective alcohols and peracetylated β-D-glucopyranoside using BF3·Et2O as catalyst. The surfactant packing parameter of the fluorinated surfactants ranged from 0.472 to 0.534 (MOPAC calculations) or 0.562 to 0.585 (calculated from literature values), which is comparable to surfactants with a similar partially fluorinated tail. Based on an initial biocompatibility assessment, the β-D-glucopyranoside surfactants have low toxicities in the B16F10 mouse melanoma cell line and comparatively low haemolytic activities towards rabbit red blood cells. The fluorinated surfactants appear to be less toxic towards cells in culture and to have a lower haemolytic activity compared to their hydrocarbon analogs. Furthermore, an increasing degree of fluorination appears to reduce both the cytotoxicity and the haemolytic activity. Similar structure–activity relationships have been reported for other partially fluorinated surfactants. Overall, these findings suggest that the surfactants may be useful for biomedical applications, such as novel drug delivery systems.

Graphical abstract: Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants

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Article information

DOI
https://doi.org/10.1039/B805015E
Article type
Paper
Submitted
02 Apr 2008
Accepted
31 Jul 2008
First published
19 Sep 2008

New J. Chem., 2008,32, 2169-2179

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Synthesis and biocompatibility evaluation of fluorinated, single-tailed glucopyranoside surfactants

X. Li, J. Turánek, P. Knötigová, H. Kudláčková, J. Mašek, D. B. Pennington, S. E. Rankin, B. L. Knutson and H. Lehmler, New J. Chem., 2008, 32, 2169 DOI: 10.1039/B805015E

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