The oxidative cleavability of protein cross-linking reagents containing organoselenium bridges

Abstract

The intensive use of cleavable cross-linking reagents to study macromolecular biological interactions has shown a demand for optimizing these reagents in such a way that the involved macromolecules remain intact. The present work focuses on the development of selenium linkers that are cleavable by mild oxidation. The efficiency of cross-linking and subsequent cross-linker cleavage with a new series of such homo- or heterobifunctional cross-linking reagents have been tested in a simple model system, consisting of albumin and cytochrome c. Resultant, or residual, covalent complex formation is examined by SDS-polyacrylamide gel electrophoresis. From this work it can be concluded that diallyl selenides are readily cleaved by mild oxidation, whereas dialkyl selenides and benzyl alkyl selenides can only be cleaved when the alkyl part of the selenide has an electron-withdrawing group next to the beta-carbon from selenium.

Catalytic generation of nitric oxide from S-nitrosothiols using immobilized organoselenium species

“…1a) and 3, 3 0 -dipropionicdiselenide (SeDPA) (see Fig. 1b) were synthesized as described in the literature [16][17][18]. Hardened filter paper (Whatman (Maidstone, UK), Grade 50) and dialysis membranes (Spectrum Laboratories Inc. (Rancho Dominguez, CA), Spectra/Por s 7) were washed before use and soaked long enough to remove trace metal ions using an EDTAcontaining buffer solution, as needed.…”

Development of a reduction-sensitive diselenide-conjugated oligoethylenimine nanoparticulate system as a gene carrier

“…When the molecular ratio of NaBH 4 to selenium was 2, colorless Na 2 Se was given as the product, and reddish brown Na 2 Se 2 was obtained at a ratio of 1. 38 To avoid H 2 Se 2 gas production as a side reaction, the pH of 3-chloropropanoic acid should be adjusted to 8.0. After reacting with 3-chloropropanoic acid overnight, Na 2 Se 2 or Na 2 Se residues should be oxidized to selenium by exposure to the atmosphere for easy purification via filtration.…”

“…Unreacted DSeDPA and SeDPA was removed by adjusting the pH of the supernatant for formation of a precipitate at pH 3-4. 38 In view of the instability of diselenide bonds in an alkaline environment (pH . 10), 43 the alkaline OEI 800 solution should be neutralized to pH 7.4 prior to cross-linking.…”

“…37,38 Selenium powder (2.37 g, 30 mmol) in 10 mL of water was added to a three-necked flask under a nitrogen atmosphere. NaBH 4 (2.27 g, 60 mmol) dissolved in 25 mL of cold H 2 O was syringed dropwise into the selenium suspension.…”

Construction and evaluation of nitric oxide generating vascular graft material loaded with organoselenium catalyst via layer-by-layer self-assembly

“…Loading of organoselenium catalyst via layer-bylayer self-assembly 3,3′-diselenodipropionic acid (SeDPA) and organoselenium immobilized polyethyleneimine (SePEI) were synthesized according to reported method [39].…”