244020-98-2Relevant academic research and scientific papers
Structural concept of nitroxide as a lipid peroxidation inhibitor
Yamasaki, Toshihide,Ito, Yuko,Mito, Fumiya,Kitagawa, Kana,Matsuoka, Yuta,Yamato, Mayumi,Yamada, Ken-Ichi
experimental part, p. 4144 - 4148 (2011/07/31)
Nitroxides have antioxidative activities toward lipid peroxidation, but the influence of steric factors is not known. We synthesized alkyl-substituted nitroxides at the α-position of the N-O moiety to enhance lipophilicity and the bulk effect. There was good correlation between the IC50 and lipophilicity (log Po/w) of nitroxides with use of the thiobarbituric acid-reactive substances (TBARS) assay. Furthermore, an inhibitory effect on the TBARS assay was dependent upon the number and length of alkyl groups, though nitroxides had almost identical lipophilicity.
Structure-reactivity relationship of piperidine nitroxide: Electrochemical, ESR and computational studies
Yamasaki, Toshihide,Mito, Fumiya,Ito, Yuko,Pandian, Sokkar,Kinoshita, Yuichi,Nakano, Koji,Murugesan, Ramachandran,Sakai, Kiyoshi,Utsumi, Hideo,Yamada, Ken-Ichi
, p. 435 - 440 (2011/04/19)
We have synthesized several nitroxides with different substituents which vary the steric and electronic environment around the N-O moiety and have systematically investigated the role of substituents on the stability of the radicals. Our results demonstrated the reactivity toward ascorbate correlates with the redox potential of the derivatives. Furthermore, ab initio calculations also indicated a correlation between the reduction rate and the computed singly occupied molecular orbital-lowest unoccupied molecular orbital energy gap, but not with solvent accessible surface area of the N-O moiety, supporting the experimental results and suggesting that the electronic factors largely determine the radicals' stability. Hence, it is possible to perform virtual screening of nitroxides to optimize their stability, which can help to rationally design novel nitroxides for their potential use in vivo.
