Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines

Nivet, J.-B.; Bernelin, R; Blanc, Maurice; Jg, Riess

doi:10.1016/0223-5234(92)90020-2

Cited by 12 publications

(11 citation statements)

References 17 publications

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“…Overall, the low IC 50 values of 13a-c and 14a-c are in agreement with a previous report that highly fluorinated 1H,1H,2H, 2H,3H,3H-perfluoroundecyltrialkylammonium salts are toxic in Namalva lymphoblastoid cells with IC 50 s below 0.16 mM. 28 The short-chain pyridinium salts 13a and 14a were the most toxic surfactants in this series with toxicities comparable with BAC. Similar results were obtained with several other cell lines (data not shown).…”

Section: Cytotoxicity and Haemolytic Assessmentssupporting

confidence: 91%

Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

et al. 2006

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Section: Cytotoxicity and Haemolytic Assessmentssupporting

confidence: 91%

Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

et al. 2006

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“…A solution of nonafluorotetradecylcarbonyl chloride (Santaella et al, 1991) (1.20 g, 2.4 mmol) in 10 mL of CHCI3 was added dropwise under argon to a solution of heptadecafluorodecylamine hydrochloride (Nivet et al, 1992) (1.16 g, 2.4 mmol) and triethylamine (1 mL, 7.3 mmol) in 10 mL of CHCI3. After 12 h, the solution was concentrated and chromatographed (silica, CHCI3) to afford 1.80 g of the amide as a white powder (90% yield).…”

Section: Methodsmentioning

confidence: 99%

Gene Transfer with a Series of Lipophilic DNA-Binding Molecules

Rémy¹,

Sirlin²,

Vierling³

et al. 1994

Bioconjugate Chem.

235

162

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Synthetic gene transfer vectors could be an attractive alternative to biological vehicles for gene therapy. In an effort to improve the previously developed lipopolyamine-mediated transfection technique, various amphiphilic DNA-binding molecules have been synthesized. Besides Transfectam, several lipospermines display very high gene delivery levels. The structure-activity relationship obtained points to the central role played by the polyamine headgroup in condensing the plasmid and binding it to the cell surface, provided the hydrophobic moiety is capable to generate nonmicellar mesomorphic structures. It also highlights other favorable (albeit more speculative) properties shared by protonable lipospermines as compared to quaternary ammonium-bearing lipids, such as their ability to act as a buffer and their strong affinity for chromatin. The former property may prevent the pH decrease along the degradative lysosomial pathway. The ability to bind to chromatin even in the presence of endogeneous polyamines should have two consequences: a nuclear tropism of the transfecting particles and plasmid uncoating in the nucleus by competitive dilution of the lipopolyamine into an ocean of DNA.

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“…The triazole, 3, was synthesized as a minor byproduct from the treatment of CF 3 (CF 2 ) 5 CH 2 CH 2 I with NaN 3 in DMF, according to the literature. 57 Cooling the crude mixture to −35 °C afforded a few crystals that were structurally characterized. Careful 1 H NMR spectroscopic analysis of the reaction mixture showed that 3 is consistently formed in low yield; the spectroscopic data confirm the formulation of 3, particularly the unique CHF group.…”

Section: ■ Introductionmentioning

confidence: 97%

Further Evidence on the Importance of Fluorous–Fluorous Interactions in Supramolecular Chemistry: A Combined Structural and Computational Study

Omorodion

Twamley

Platts

et al. 2015

Crystal Growth & Design

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The solid-state structures of CF3(CF2)5CH2CO2H and a fluorous triazole are reported, both of which display a wide variety and large number of noncovalent interactions in their packing. The solid-state structure of CF3(CF2)5CH2CO2H is stabilized by multiple F···F contacts but only one C–H···F–C interaction, as well as O–H···O and C–H···O hydrogen bonds. In contrast to other reported structures, the torsion angles in the fluorous chain are close to 180°, which means that the fluorine atoms are eclipsed. A DFT study of the interactions in both compounds show that F···F interactions, along with stacking and C–H···F and C–H···O contacts, are individually weakly energetically stabilizing, but collectively, they can give rise to interaction energies of up to 13 kcal mol–1. A topological approach to the interactions using atoms-in-molecules (AIM) theory reveals that there are bond critical points between the C–F···F–C interactions as well as C–F···H–C interactions that are not recognized when using only the van der Waals distances.

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Synthesis and bioacceptability of fluorinated surfactants derived from F-alkylated tertiary amines

Cited by 12 publications

References 17 publications

Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

Synthesis and biocompatibility evaluation of partially fluorinated pyridinium bromides

Gene Transfer with a Series of Lipophilic DNA-Binding Molecules

Further Evidence on the Importance of Fluorous–Fluorous Interactions in Supramolecular Chemistry: A Combined Structural and Computational Study

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