Free-radical scavenging by tryptophan and its metabolites through electron transfer based processes
| LEADER | caa a22 4500 | ||
|---|---|---|---|
| 001 | 605512973 | ||
| 003 | CHVBK | ||
| 005 | 20210128100658.0 | ||
| 007 | cr unu---uuuuu | ||
| 008 | 210128e20150801xx s 000 0 eng | ||
| 024 | 7 | 0 | |a 10.1007/s00894-015-2758-2 |2 doi |
| 035 | |a (NATIONALLICENCE)springer-10.1007/s00894-015-2758-2 | ||
| 245 | 0 | 0 | |a Free-radical scavenging by tryptophan and its metabolites through electron transfer based processes |h [Elektronische Daten] |c [Adriana Pérez-González, Juan Alvarez-Idaboy, Annia Galano] |
| 520 | 3 | |a Free-radical scavenging by tryptophan and eight of its metabolites through electron transfer was investigated in aqueous solution at physiological pH, using density functional theory and the Marcus theory. A test set of 30 free radicals was employed. Thermochemical and kinetic data on the corresponding reactions are provided here for the first time. Two different pathways were found to be the most important: sequential proton loss electron transfer (SPLET) and sequential double proton loss electron transfer (SdPLET). Based on kinetic analyses, it is predicted that the tryptophan metabolites kynurenic acid and xanthurenic acid are the best free-radical scavengers among the tested compounds; they were estimated to be at least 24 and 12 times more efficient than Trolox for scavenging •OOH. These findings are in line with previous reports suggesting that the antioxidant activity that has been attributed to tryptophan is actually due to its metabolites, and they demonstrate the particular importance of phenolic metabolites to such activity. Graphical Abstract Kynurenic acid (KNA) and xanthurenic acid (XNA) are the major contributors to the free-radical scavenging activity of tryptophan | |
| 540 | |a Springer-Verlag Berlin Heidelberg, 2015 | ||
| 690 | 7 | |a Free-radical scavenger |2 nationallicence | |
| 690 | 7 | |a Rate constants |2 nationallicence | |
| 690 | 7 | |a Single electron transfer |2 nationallicence | |
| 700 | 1 | |a Pérez-González |D Adriana |u Departamento de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México, 04510, México, DF, Mexico |4 aut | |
| 700 | 1 | |a Alvarez-Idaboy |D Juan |u Departamento de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México, 04510, México, DF, Mexico |4 aut | |
| 700 | 1 | |a Galano |D Annia |u Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina. Iztapalapa, C. P. 09340, México, DF, Mexico |4 aut | |
| 773 | 0 | |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/8(2015-08-01), 1-11 |x 1610-2940 |q 21:8<1 |1 2015 |2 21 |o 894 | |
| 856 | 4 | 0 | |u https://doi.org/10.1007/s00894-015-2758-2 |q text/html |z Onlinezugriff via DOI |
| 898 | |a BK010053 |b XK010053 |c XK010000 | ||
| 900 | 7 | |a Metadata rights reserved |b Springer special CC-BY-NC licence |2 nationallicence | |
| 908 | |D 1 |a research-article |2 jats | ||
| 949 | |B NATIONALLICENCE |F NATIONALLICENCE |b NL-springer | ||
| 950 | |B NATIONALLICENCE |P 856 |E 40 |u https://doi.org/10.1007/s00894-015-2758-2 |q text/html |z Onlinezugriff via DOI | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Pérez-González |D Adriana |u Departamento de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México, 04510, México, DF, Mexico |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Alvarez-Idaboy |D Juan |u Departamento de Física y Química Teórica, Facultad de Química, Universidad Nacional Autónoma de México, 04510, México, DF, Mexico |4 aut | ||
| 950 | |B NATIONALLICENCE |P 700 |E 1- |a Galano |D Annia |u Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina. Iztapalapa, C. P. 09340, México, DF, Mexico |4 aut | ||
| 950 | |B NATIONALLICENCE |P 773 |E 0- |t Journal of Molecular Modeling |d Springer Berlin Heidelberg |g 21/8(2015-08-01), 1-11 |x 1610-2940 |q 21:8<1 |1 2015 |2 21 |o 894 | ||