TELOMERS AND COTELOMERS OF BIOLOGICAL AND BIOMEDICAL SIGNIFICANCE .4. TELOMERS OF TRIS(HYDROXYMETHYL)ACRYLAMIDOMETHANE, NEW NONIONIC AMPHIPHILIC AGENTS

The synthesis of a new class of non-ionic detergents, suitable for the extraction of membrane proteins and/or glycoproteins is reported. These amphiphilic molecules were obtained by free radical telomerization of tris-(hydroxymethyl)-acrylamidomethane derivatives in the presence of an alkanethiol as chain-transfer reagent. Compounds with DPBARn greater-than-or-equal-to 3 are readily soluble in water. Critical micellar concentrations (CMC) range from 10(-2) to 2.10(-5) M depending on the hydrocarbon moiety. Detergent properties were assessed on membranes and compared to those of commonly used detergents such as Triton X-100 and Tween-20; telomers of tris-(hydroxymethyl)-acrylamidomethane (TAC) show either similar or better efficiency than these detergents in all type of evaluations. In addition, TAC derivatives do not absorb between 250 and 350 nm. Moreover dialysis was completed within 10 hr and LD50 was shown to be 750 mg/kg in mice, by i.v. injection.