Kinetics and Mechanism of Bilirubin Oxidation by Benzoyl Peroxide in Dimethyl Sulfoxide

Autor:	Alexey V. Solomonov, Evgeniy V. Rumyantsev, Maria K. Serebryakova, Sergei P. Ivanov
Rok vydání:	2014
Předmět:	Biliverdin Antioxidant Dimethyl sulfoxide Radical medicine.medical_treatment Organic Chemistry Kinetics Benzoyl peroxide Photochemistry Biochemistry Redox Inorganic Chemistry chemistry.chemical_compound chemistry medicine Physical and Theoretical Chemistry Methylene medicine.drug
Zdroj:	International Journal of Chemical Kinetics. 47:27-35
ISSN:	0538-8066
Popis:	The kinetics of the redox reaction of bilirubin by the action of benzoyl peroxide in dimethyl sulfoxide was analyzed. It is shown that the first reaction product is biliverdin, which oxidizes to purpurin and further to choletelin. The kinetic and activation parameters of the oxidation reactions were obtained. A kinetic model of the process was proposed. An assumed route of the reaction is related to the exchange interaction of CH protons of methylene and methine spacers with free radicals in the rate-limiting step with the further destruction of the “ridge-tile” pigment conformation. The mechanism steps are confirmed by quantum-chemical calculations and HPLC. It is found that in organic solvents the end products of bilirubin oxidation are not monopyrrolic derivatives. The data obtained will be useful in constructing antioxidant action models of the pigment.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::63d2306d747d0a659920f816eb0fc0cf https://doi.org/10.1002/kin.20889 Zobrazit plný text záznamu Plný text