A tri(potassium sulfonate) derivative of perchlorotriphenylmethyl radical (PTM) as a stable water soluble radical-scavenger of the hydroxyl radical more powerful than 5,5-dimethyl-1-pyrroline-N-oxide

被引:5
作者
Antonio Mesa, Juan [1 ]
Chavez, Sergei [1 ]
Fajari, Lluis [1 ]
Lluis Torres, Josep [1 ]
Julia, Luis [1 ]
机构
[1] CSIC, IQAC, Dept Quim Biol & Modelitzacio Mol, ES-08034 Barcelona, Spain
关键词
ELECTRON-TRANSFER CAPACITY; INDUCED OXIDATIVE STRESS; FENTON REACTION; ANTIOXIDANT ACTIVITY; FLUORESCENT-PROBE; SUPEROXIDE; HYDROGEN; SERIES; ESR; POLYPHENOLS;
D O I
10.1039/c3ra41499j
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
The tripotassium salt of tris(2,3,5,6-tetrachloro-4-hydroxysulfonylphenyl) methyl radical (3 K+ TSPTM3-) reacts in water with hydroxyl radical very fast with a rate constant (k = 2.4 x 10(11) M-1 s(-1)) much higher than that of the reaction of hydroxyl radical with the spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO) (k = 3.4 x 10(9) M-1 s(-1)). The reaction affects the radical character of the molecule and is monitored by electron paramagnetic resonance (EPR). The hydroxyl radical scavenging is established by the characterization of the resulting water-soluble product as the dipotassium salt of 4-[ bis(2,3,5,6-tetrachloro-4-hydroxysulfonylphenyl) methylene]-2,3,5,6-tetrachlorocyclohexa-2,5-dien-1-one (2).
引用
收藏
页码:9949 / 9956
页数:8
相关论文
共 53 条
[1]
Selective control of the radical-scavenging activity of poly(phenols) in aqueous media in terms of their electron-donor properties, using a stable organic radical as chemical sensor [J].
Antonio Mesa, Juan ;
Lluis Torres, Josep ;
Julia, Luis .
TALANTA, 2012, 101 :141-147
[2]
Synthesis of a new stable and water-soluble tris(4-hydroxysulfonyl-tetrachlorophenyl)methyl radical with selective oxidative capacity [J].
Antonio Mesa, Juan ;
Velazquez-Palenzuela, Amado ;
Brillas, Enric ;
Lluis Torres, Josep ;
Julia, Luis .
TETRAHEDRON, 2011, 67 (17) :3119-3123
[3]
BAKER MS, 1984, ARCH BIOCHEM BIOPHYS, V234, P258, DOI 10.1016/0003-9861(84)90348-5
[4]
INERT CARBON FREE-RADICALS .3. MONOFUNCTIONALIZED RADICALS FROM PERCHLOROTRIPHENYLCARBENIUM HEXACHLOROANTIMONATE [J].
BALLESTER, M ;
RIERA, J ;
CASTANER, J ;
RODRIGUEZ, A ;
ROVIRA, C ;
VECIANA, J .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4498-4505
[5]
Barbusinski K, 2009, ECOL CHEM ENG S, V16, P347
[6]
pH-induced mechanistic changeover from hydroxyl radicals to iron(IV) in the Fenton reaction [J].
Bataineh, Hajem ;
Pestovsky, Oleg ;
Bakac, Andreja .
CHEMICAL SCIENCE, 2012, 3 (05) :1594-1599
[7]
SPIN TRAPPING - ELECTRON-SPIN-RESONANCE PARAMETERS OF SPIN ADDUCTS [J].
BUETTNER, GR .
FREE RADICAL BIOLOGY AND MEDICINE, 1987, 3 (04) :259-303
[8]
2 FUNCTIONALIZED FREE-RADICALS OF THE TRIS(2,4,6-TRICHLOROPHENYL)METHYL RADICAL SERIES - SYNTHESIS, STABILITY AND EPR ANALYSIS [J].
CARILLA, J ;
FAJARI, L ;
JULIA, L ;
RIERA, J ;
VIADEL, L .
TETRAHEDRON LETTERS, 1994, 35 (35) :6529-6532
[9]
Punicalagin and Catechins Contain Polyphenolic Substructures That Influence Cell Viability and Can Be Monitored by Radical Chemosensors Sensitive to Electron Transfer [J].
Carreras, Anna ;
Luisa Mateos-Martin, Maria ;
Velazquez-Palenzuela, Amado ;
Brillas, Enric ;
Cascante, Marta ;
Julia, Luis ;
Lluis Torres, Josep .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (07) :1659-1665
[10]
Oxidant Activity of Tris(2,4,6-trichloro-3,5-dinitrophenyl)methyl Radical with Catechol and Pyrogallol. Mechanistic Considerations [J].
Carreras, Anna ;
Esparbe, Isaac ;
Brillas, Enric ;
Rius, Jordi ;
Torres, Josep Lluis ;
Julia, Luis .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (06) :2368-2373