Redox regulation of tumor cell toxicity by flavones from Lethedon tannaensis

被引:6
作者
Bensasson, RV
Jossang, A
Zahir, A
Bodo, B
Land, EJ
机构
[1] Museum Natl Hist Nat, Biophys Lab, CNRS, UMR 8646,INSERM U201, F-75231 Paris 05, France
[2] Museum Natl Hist Nat, Chim Lab, CNRS, ESA 8041, F-75231 Paris, France
[3] Christie Hosp NHS Trust, Paterson Inst Canc Res, CRC, Sect Drug Dev & Imaging, Manchester, Lancs, England
关键词
tumor cell toxicity; redox regulation; flavones; Lethedon tannaensis; singlet oxygen quenching; reduction potential; nasopharynx carcinoma cells; antitumor drugs; free radicals;
D O I
10.1016/S0891-5849(99)00039-8
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The purpose of the present work has been to seek a correlation of potential predictive value, demonstrating redox control of cytotoxicity toward human nasopharynx carcinoma (KB) cells by seven 5-hydroxy-7-methoxyflavones, together with two glycoside derivatives, all extracted from Lethedon tannaensis, In this approach, redox control is characterized by a physicochemical parameter expressing quantitatively the relative electron-donating power of the flavones, this parameter being the second order rate constant, k(Delta), for quenching of singlet oxygen O-2 ((1)Delta g). This rate constant k(Delta) is usually related to the ability of a given molecule D to donate an electron and, thus, with the reduction potential E of the couple (D.+/D). Our results show that the flavone toxicity is linearly correlated with ease of oxidation: the higher the rate constant of reaction with singlet oxygen, the easier the oxidation, the less positive or more negative the reduction potential (D.+/D), the higher the cytotoxicity. The results suggest new screening strategies to identify and improve potential antitumor drugs. (C) 1999 Elsevier Science Inc.
引用
收藏
页码:95 / 99
页数:5
相关论文
共 42 条
[1]  
BARD AJ, 1980, ELECTROCHEMICAL METH
[2]  
BELLUS D, 1978, SINGLET OXYGEN REACT, P61
[3]  
BENSASSON RV, 1992, MOL PHARMACOL, V42, P718
[4]   FLAVONE ACETIC-ACID FROM LABORATORY TO CLINIC AND BACK [J].
BIBBY, MC ;
DOUBLE, JA .
ANTI-CANCER DRUGS, 1993, 4 (01) :3-17
[5]   Antioxidant and prooxidant behavior of flavonoids: Structure-activity relationships [J].
Cao, GH ;
Sofic, E ;
Prior, RL .
FREE RADICAL BIOLOGY AND MEDICINE, 1997, 22 (05) :749-760
[6]   Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups [J].
Chen, ZY ;
Chan, PT ;
Ho, KY ;
Fung, KP ;
Wang, J .
CHEMISTRY AND PHYSICS OF LIPIDS, 1996, 79 (02) :157-163
[7]   HYDRAZINES - NEW CHARGE-TRANSFER PHYSICAL QUENCHERS OF SINGLET OXYGEN [J].
CLENNAN, EL ;
NOE, LJ ;
SZNELER, E ;
WEN, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (13) :5080-5085
[8]  
CORBETT TH, 1986, INVEST NEW DRUG, V4, P207
[9]   Antioxidant properties of hydroxy-flavones [J].
Cotelle, N ;
Bernier, JL ;
Catteau, JP ;
Pommery, J ;
Wallet, JC ;
Gaydou, EM .
FREE RADICAL BIOLOGY AND MEDICINE, 1996, 20 (01) :35-43
[10]   STRUCTURE ACTIVITY RELATIONSHIP OF MUTAGENIC AROMATIC AND HETEROAROMATIC NITRO-COMPOUNDS - CORRELATION WITH MOLECULAR-ORBITAL ENERGIES AND HYDROPHOBICITY [J].
DEBNATH, AK ;
DECOMPADRE, RLL ;
DEBNATH, G ;
SHUSTERMAN, AJ ;
HANSCH, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :786-797