PMID- 17845855
OWN - NLM
STAT- MEDLINE
DCOM- 20080124
LR  - 20131121
IS  - 0968-0896 (Print)
IS  - 0968-0896 (Linking)
VI  - 15
IP  - 22
DP  - 2007 Nov 15
TI  - Antioxidant properties and free radical-scavenging reactivity of a family of 
      hydroxynaphthalenones and dihydroxyanthracenones.
PG  - 7058-65
AB  - This study was undertaken to investigate the free radical-scavenging and 
      antioxidant activities of various structurally related hydroquinones including 
      hydroxynaphthalenones and dihydroxyanthracenones. Electron spin resonance 
      spectroscopy and spin trapping techniques were used to evaluate the ability of 
      hydroquinones to scavenge hydroxyl, diphenylpicrylhydrazyl, and galvinoxyl 
      radicals. In addition, the oxygen radical absorbing capacity assay using 
      fluorescein (ORAC-FL) was used to obtain the relative antioxidant capacity of 
      these radicals. The rate constants of the first H atom abstraction by 
      2,2-diphenyl-2-picrylhydrazyl (k(2)), were obtained under pseudo-first-order 
      conditions. The free radical-scavenging activities and k(2) values discriminate 
      well between hydroxynaphthalenones and dihydroxyanthracenones, showing that the 
      latter have better antioxidant properties. The aforementioned experimental data 
      agree with quantum-chemical results demonstrating the relevance of intramolecular 
      H bonding to radical-scavenging activities.
FAU - Rodriguez, Jorge
AU  - Rodriguez J
AD  - Departamento de Quimica Inorganica y Analitica, Facultad de Ciencias Quimicas y 
      Farmaceuticas, Universidad de Chile, Chile.
FAU - Olea-Azar, Claudio
AU  - Olea-Azar C
FAU - Cavieres, Cristina
AU  - Cavieres C
FAU - Norambuena, Ester
AU  - Norambuena E
FAU - Delgado-Castro, Tomas
AU  - Delgado-Castro T
FAU - Soto-Delgado, Jorge
AU  - Soto-Delgado J
FAU - Araya-Maturana, Ramiro
AU  - Araya-Maturana R
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20070807
PL  - England
TA  - Bioorg Med Chem
JT  - Bioorganic & medicinal chemistry
JID - 9413298
RN  - 0 (Anthracenes)
RN  - 0 (Antioxidants)
RN  - 0 (Free Radical Scavengers)
RN  - 0 (Naphthalenes)
RN  - 0 (Reactive Oxygen Species)
RN  - S88TT14065 (Oxygen)
SB  - IM
MH  - Animals
MH  - Anthracenes/*chemistry/pharmacology
MH  - Antioxidants/*chemistry/pharmacology
MH  - Cell Line, Tumor
MH  - Electron Spin Resonance Spectroscopy/methods
MH  - Free Radical Scavengers/*chemistry/pharmacology
MH  - Hydrogen Bonding
MH  - Kinetics
MH  - Mice
MH  - Molecular Structure
MH  - Naphthalenes/*chemistry/pharmacology
MH  - Oxygen/antagonists & inhibitors/*chemistry/metabolism
MH  - Reactive Oxygen Species/chemistry/metabolism
MH  - Reproducibility of Results
MH  - Sensitivity and Specificity
EDAT- 2007/09/12 09:00
MHDA- 2008/01/25 09:00
CRDT- 2007/09/12 09:00
PHST- 2007/04/24 00:00 [received]
PHST- 2007/07/17 00:00 [revised]
PHST- 2007/07/18 00:00 [accepted]
PHST- 2007/09/12 09:00 [pubmed]
PHST- 2008/01/25 09:00 [medline]
PHST- 2007/09/12 09:00 [entrez]
AID - S0968-0896(07)00657-8 [pii]
AID - 10.1016/j.bmc.2007.07.013 [doi]
PST - ppublish
SO  - Bioorg Med Chem. 2007 Nov 15;15(22):7058-65. doi: 10.1016/j.bmc.2007.07.013. Epub 
      2007 Aug 7.