NDLI: Hydroxycinnamic Acids as DNA-Cleaving Agents in the Presence of $Cu^{II}$ Ions: Mechanism, Structure–Activity Relationship, and Biological Implications

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Hydroxycinnamic Acids as DNA-Cleaving Agents in the Presence of $Cu^{II}$ Ions: Mechanism, Structure–Activity Relationship, and Biological Implications

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Hydroxycinnamic Acids as DNA-Cleaving Agents in the Presence of $Cu^{II}$ Ions: Mechanism, Structure–Activity Relationship, and Biological Implications

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Qian, Yi-ping Jin, Xiao-ling Dai, Fang Tang, Jiang-jiang Zhou, Bo Wang, Qi Yang, Jie Fan, Gui-juan Cheng, Li-xia Shang, Ya-jing Yang, Ru-ting
Description	Author Affiliation: Fan GJ ( State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, China.)
Abstract	The effectiveness of hydroxycinnamic acids (HCAs), that is, caffeic acid (CaA), chlorogenic acid (ChA), sinapic acid (SA), ferulic acid (FA), 3-hydroxycinnamic acid (3-HCA), and 4-hydroxycinnamic acid (4-HCA), as pBR322 plasmid DNA-cleaving agents in the presence of $Cu^{II}$ ions was investigated. Compounds bearing o-hydroxy or 3,5-dimethoxy groups on phenolic rings (CaA, SA, and ChA) were remarkably more effective at causing DNA damage than the compounds bearing no such groups; furthermore, CaA was the most active among the HCAs examined. The involvement of reactive oxygen species (ROS) and $Cu^{I}$ ions in the DNA damage was affirmed by the inhibition of the DNA breakage by using specific scavengers of ROS and a $Cu^{I}$ chelator. The interaction between CaA and $Cu^{II}$ ions and the influence of ethylenediaminetetraacetic acid (EDTA), the solvent, and pH value on the interaction were also studied to help elucidate the detailed prooxidant mechanism by using UV/Vis spectroscopic analysis. On the basis of these observations, it is proposed that it is the CaA phenolate anion, instead of the parent molecule, that chelates with the $Cu^{II}$ ion as a bidentate ligand, hence facilitating the intramolecular electron transfer to form the corresponding CaA semiquinone radical intermediate. The latter undergoes a second electron transfer with oxygen to form the corresponding o-quinone and a superoxide, which play a pivotal role in the DNA damage. The intermediacy of the semiquinone radical was supported by isolation of its dimer from the $Cu^{II}-mediated$ oxidation products. Intriguingly, CaA was also the most cytotoxic compound among the HCAs toward human promyelocytic leukemia (HL-60) cell proliferation. Addition of exogenous $Cu^{II}$ ions resulted in an effect dichotomy on cell viability depending on the concentration of CaA; that is, low concentrations of CaA enhanced the cell viability and, conversely, high concentrations of CaA almost completely inhibited the cell proliferation. On the other hand, when superoxide dismutase was added before, the two stimulation effects of exogenous $Cu^{II}$ ions were significantly ameliorated, thus clearly indicating that the oxidative-stress level regulates cell proliferation and death. These findings provide direct evidence for the antioxidant/prooxidant mechanism of cancer chemoprevention.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	46
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-11-23
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Copper Pharmacology Coumaric Acids Chemistry DNA Cell Proliferation Drug Effects Metabolism DNA Breaks Edetic Acid HL-60 Cells Hydrogen-Ion Concentration Oxidation-Reduction Plasmids Reactive Oxygen Species Solvents Spectrophotometry, Ultraviolet Structure-Activity Relationship Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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