Effects of phosphonium compounds on Schistosoma mansoni

Abstract

A new series of phosphonium salts was examined for effects on the cholinergic nervous system of Schistosoma mansoni. Studies were conducted using both an activity-monitoring and fluorescent-labeling technique. The activity method gave more definitive results, indicating that some poly(methylene)bis(triphenylphosphonium) salts and some [3-(alkylamino)propyl]triphenylphosphonium salts have strong anticholinergic effects. Hexyltriphenylphosphonium bromide has very marked effects both in the motility and the fluorescence test, but these effects cannot immediately be ascribed to cholinergic actions.

(5-Ammoniopentyl)triphenylphosphonium dibromide ethanol solvate

“…For the development and applications of mitochondrially targeted bio-active compounds, see: Murphy & Smith (2007); Porteous et al (2010); Prime et al (2009). For the synthesis and applications of aminoalkyl triphenylphosphonium salts, see: Issleib & Rieschel (1965); Keough & Grayson (1964); McAllister et al (1980). For related structures, see: Czerwinski (1986); Dubourg et al (1986).…”

“…In the course of our research in mitochondrially targeted bio-active agents (Murphy & Smith, 2007), 5-ammoniopentyl triphenylphosphonium dibromide was prepared as a precursor for both a targeted thionitrite (Prime et al, 2009) and an iodoacetamide (Porteous et al, 2010). Aminoalkyl-triphenylphosphonium salts are well known (McAllister et al, 1980;Keough & Grayson, 1964;Issleib & Rieschel, 1965) but to date only dimethylamino-3-propyl triphenylphosphonium chloride (Dubourg et al, 1986) and 2-aminoethyl triphenylphosphonium bromide hydrogen bromide (Czerwinski, 1986) have been structurally characterized. The latter is clearly a dication with two bromide anions whereas the former contains a singly charged aminoalkyl triphenylphosphonium cation.…”

“…The title compound was prepared using a modified procedure to that published (McAllister et al, 1980). Crystalline 5bromopentyl-amine hydrogen bromide (3 mmol) and excess triphenylphosphine (9 mmol) were heated under an inert atmosphere to 100°C and stirred for 72 h. After cooling to room temperature, the mixture was dissolved in ethanol (5 mL) and added to diethyl ether (20 mL) to precipitate the compound.…”

[3-(Iodoacetamido)propyl]triphenylphosphonium tetraphenylborate

“…For the use of iodoacetamides in labelling cysteine residues, see Baty et al (2002); Kim et al (2000); Ying et al (2007). For the synthesis of aminoalkyl triphenylphosphonium salts, see McAllister et al (1980). For the synthesis of iodoacetamides, see Trujillo et al (1991).…”

“…The title compound was prepared from 3-aminopropyl triphenylphosphonium bromide hydrogen bromide (prepared using methods similar to McAllister et al, 1980) using a modified literature procedure (Trujillo et al, 1991). Triethylamine (0.43 mmol) was added to a dichloromethane solution (20 mL) of 3-aminopropyl triphenylphosphonium bromide hydrogen bromide (0.43 mmol), the solution cooled to -70°C and solid p-nitrophenyl iodoacetate (0.43 mmol) added in one portion.…”