Journal article
Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides
New Journal of Chemistry, Vol.3(6), pp.944-951
06/05/2006
DOI: 10.1039/b516039a
Abstract
Although cationic surfactants are of general interest for a variety of consumer and biomedical applications, only a limited number of partially fluorinated, single-tailed, cationic surfactants have been synthesized. To study the potential usefulness of fluorinated cationic surfactants for these applications we synthesized a series of partially fluorinated pyridinium bromide surfactants. Three 10-perfluoroalkyldecyl pyridinium surfactants were synthesized by coupling a perfluoroalkyl iodide with 9-decene-1-yl acetate using an AIBN mediated radical reaction. The resulting 9-iodo-10-perfluoroalkyldec-1-yl acetates were deiodinated using HI-Zn-EtOH and hydrolyzed using KOH-EtOH to yield the corresponding 10-perfluoroalkyldecanol. The partially fluorinated alcohol was converted into the bromide using Br
2
-PPh
3
. Alkylation of excess pyridine with the bromides gave the desired 10-perfluoroalkyldecyl pyridinium bromides in good yields. Three 10-perfluoroalkylundecyl surfactants were synthesized using a similar approach with 10-undecenoic acid methyl ester as starting material. Based on an initial
in vitro
toxicity assessment, the toxicity of the partially fluorinated pyridinium surfactants was slightly lower or comparable to benzalkonium chloride, a typically cationic surfactant (with IC
50
s of tested compounds ranging from 5 to 15 μM). An increase in the length and or the degree of fluorination of the hydrophobic tail correlated with a mild decrease of cytotoxicity and haemolytic activity. Partially fluorinated pyridinium surfactants may, therefore, be useful for biomedical applications such as components for novel gene and drug delivery systems.
The synthesis and biocompatibility assessment of partially fluorinated pyridinium surfactants is described.
Details
- Title: Subtitle
- Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides
- Creators
- Sandhya M VyasJaroslav TuránekPavlína KnötigováAndrea KašnáVeronika KvardováVenkat KogantiStephen E RankinBarbara L KnutsonHans-Joachim Lehmler
- Resource Type
- Journal article
- Publication Details
- New Journal of Chemistry, Vol.3(6), pp.944-951
- DOI
- 10.1039/b516039a
- ISSN
- 1144-0546
- eISSN
- 1369-9261
- Number of pages
- 8
- Date published
- 06/05/2006
- Academic Unit
- Occupational and Environmental Health; Iowa Neuroscience Institute
- Record Identifier
- 9984000923502771
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