Dendritic antioxidants with pyrazole as the core: ability to scavenge radicals and to protect DNA.
Chalcones with or without a para-hydroxyl group were condensed with phenylhydrazine-related compounds to form 1,3,5-triphenyl-1H-pyrazole (TPP), 4-(1,5-diphenyl-1H-pyrazol-3-yl)phenol (APP), 4-(1,3-diphenyl-1H-pyrazol-5-yl)phenol (BPP), and 4-(3,5-diphenyl-1H-pyrazol-1-yl)phenol (CPP), in which the phenyl group formed a dendritic structure with pyrazole as the core. Thus, the aim of this work was to explore the antioxidant capacities of TPP, APP, BPP, and CPP in trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+•)) and 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) and in inhibiting Cu(2+)/glutathione (GSH)-, (•)OH-, and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. TPP can react with ABTS(+•) and DPPH, indicating that the N atom in pyrazole possesses radical-scavenging ability. Moreover, APP, BPP, and CPP can trap 1.71, 1.81, and 1.58 radicals, respectively, in protecting DNA against AAPH-induced oxidation. Thus, the combination of pyrazole with a phenyl group exerted antioxidant ability although only one phenolic hydroxyl group was involved. However, these compounds showed weak protective effect against Cu(2+)/GSH-induced oxidation of DNA and even a pro-oxidant effect on (•)OH-induced oxidation of DNA.
Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
Yan-Feng
YF
Li
Zai-Qun
ZQ
Liu
D052160:Benzothiazoles / Q000037:antagonists & inhibitors / Q000737:chemistry; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors / Q000737:chemistry; D047188:Chalcones / Q000737:chemistry*; D003300:Copper / Q000037:antagonists & inhibitors / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D003712:Dendrites / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry*; D005978:Glutathione / Q000037:antagonists & inhibitors / Q000737:chemistry; D017665:Hydroxyl Radical / Q000037:antagonists & inhibitors / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D010659:Phenylhydrazines / Q000737:chemistry*; D010851:Picrates / Q000037:antagonists & inhibitors / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry*; D017382:Reactive Oxygen Species / Q000037:antagonists & inhibitors* / Q000737:chemistry; D013053:Spectrophotometry; D013451:Sulfonic Acids / Q000037:antagonists & inhibitors / Q000737:chemistry
D052160:Benzothiazoles; D001713:Biphenyl Compounds; D047188:Chalcones; D016166:Free Radical Scavengers; D010636:Phenols; D010659:Phenylhydrazines; D010851:Picrates; D011720:Pyrazoles; D017382:Reactive Oxygen Species; D013451:Sulfonic Acids; C002502:2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid; D017665:Hydroxyl Radical; D003300:Copper; D004247:DNA; C004931:1,1-diphenyl-2-picrylhydrazyl; D005978:Glutathione