Effect of bovine serum albumin on the water solubility of hydrophobic corrinoids

Abstract

Medicinal effects of hydrophobic derivatives of vitamin [Formula: see text] have been insignificantly investigated primarily due to their low solubility in aqueous solutions. One of the ways to increase their water solubility is the complexation with proteins. Here, we report the results of the studies of the reactions between aquacyano cobyrinic acid or monocyano cobesters (i.e., heptamethyl, heptaethyl, heptapropyl, and heptabutyl cobyrinates) and bovine serum albumin (BSA). The weakest binding is observed between aquacyano cobyrinic acid and BSA. In the case of monocyano heptaethyl cobyrinate, one BSA molecule is capable of binding up to six corrinoid molecules preventing its precipitation. Moreover, the pronounced effect of BSA on the solubility in water was observed in the case of monocyano heptapropyl cobyrinate. The absence of the precipitation of monocyano heptabutyl cobyrinate was observed only in the presence of high excess of BSA. BSA modification by diethyl pyrocarbonate, a chemical predominantly reactive toward imidazole motifs, indicated that a major fraction of BSA is bound with monocyano heptaethyl, heptapropyl, and heptabutyl cobyrinates via histidine residues. We showed that nitrosyl complexes of heptaethyl and heptapropyl cobyrinates can be stabilized from precipitation in aqueous solutions using BSA.

High Reactivity of Supermolecular Nanoentities of a Vitamin B12 Derivative in Langmuir–Schaefer Films Toward Gaseous Toxins

“…Addition of NH 3 gas to SMEs of (CN − ) Bu Cby in LS films results in the formation of species with maxima in the UV−vis spectrum at 361 and 553 nm (Figure 5). This spectrum is close to the UV− vis spectra of hydroxocyano species or amino complexes of monocyano incomplete corrinoids (e.g., cobinamide, 10 heptamethyl cobyrinate, 66 and others). Incubation of the (CN − ) Bu Cby LS film after the reaction with NH 3 under vacuum, in an argon flow, or in the air for a prolonged time (up to 2 weeks) results in its almost negligible regeneration (Figure S17).…”

“…The dicyano form of heptabutyl cobyrinate was synthesized according to reported protocols. , It included heating of CNCbl (50 mg) at 60 °C with dry butanol (4 mL) in the presence of sulfuric acid (1 M) under anaerobic conditions for 4 days. The reaction mixture was neutralized by NaHCO 3 , and the product was extracted by dichloromethane in the presence of KCN.…”