Electrochemical detection of in situ adriamycin oxidative damage to DNA

被引:126
作者
Oliveira-Brett, AM [1 ]
Vivan, M
Fernandes, IR
Piedade, JAP
机构
[1] Univ Coimbra, Fac Ciencias & Tecnol, Dept Quim, P-3004535 Coimbra, Portugal
[2] Hosp Univ Coimbra, P-3000075 Coimbra, Portugal
关键词
adriamycin; DNA-biosensor; oxidative damage; 8-oxoguanine; voltammetry;
D O I
10.1016/S0039-9140(01)00656-7
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Adriamycin intercalation and in situ interaction with double helix DNA was investigated using a voltammetric DNA-biosensor. Oxidation and reduction of adriamycin molecules intercalated in double helix DNA were investigated in order to understand the in vivo mechanism of action with this anti-neoplasic drug. The results showed that the interaction of adriamycin with DNA is potential-dependent causing contact between DNA guanine and adenine bases and the electrode surface such that their oxidation is easily detected. A mechanism for adriamycin reduction and oxidation in situ when intercalated in double helix DNA immobilised onto the glassy carbon electrode surface is presented and the formation of the mutagenic 8-oxoguanine explained. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:959 / 970
页数:12
相关论文
共 34 条
[1]   ELECTROCHEMICAL-BEHAVIOR OF ADRIAMYCIN AT CARBON PASTE ELECTRODES [J].
BALDWIN, RP ;
PACKETT, D ;
WOODCOCK, TM .
ANALYTICAL CHEMISTRY, 1981, 53 (03) :540-542
[2]   INTERACTION OF ANTHRACYCLINE ANTIBIOTICS WITH BIO-POLYMERS .5. POLAROGRAPHIC-BEHAVIOR AND COMPLEXES WITH DNA [J].
BERG, H ;
HORN, G ;
LUTHARDT, U ;
IHN, W .
BIOELECTROCHEMISTRY AND BIOENERGETICS, 1981, 8 (05) :537-553
[3]  
Blackburn G. M., 1996, NUCL ACIDS CHEM BIOL
[4]   Electrochemical determination of carboplatin in serum using a DNA-modified glassy carbon electrode [J].
Brett, AMO ;
Serrano, SHP ;
Macedo, TA ;
Raimundo, D ;
Marques, MH ;
LaScalea, MA .
ELECTROANALYSIS, 1996, 8 (11) :992-995
[5]   Oxidative nucleobase modifications leading to strand scission [J].
Burrows, CJ ;
Muller, JG .
CHEMICAL REVIEWS, 1998, 98 (03) :1109-1151
[6]   INDUCTION OF STABLE TRANSCRIPTIONAL BLOCKAGE SITES BY ADRIAMYCIN - GPC SPECIFICITY OF APPARENT ADRIAMYCIN DNA ADDUCTS AND DEPENDENCE ON IRON(III) IONS [J].
CULLINANE, C ;
PHILLIPS, DR .
BIOCHEMISTRY, 1990, 29 (23) :5638-5646
[7]   Chemistry of glycosylases and endonucleases involved in base-excision repair [J].
David, SS ;
Wiliams, SD .
CHEMICAL REVIEWS, 1998, 98 (03) :1221-1261
[8]   Doxorubicin and mechanical performance of cardiac trabeculae after acute and chronic treatment: a review [J].
De Beer, EL ;
Bottone, AE ;
Voest, EE .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2001, 415 (01) :1-11
[9]  
DIMARCO A, 1969, CANCER CHEMOTH REP 1, V53, P33
[10]   STRUCTURAL COMPARISON OF ANTICANCER DRUG DNA COMPLEXES - ADRIAMYCIN AND DAUNOMYCIN [J].
FREDERICK, CA ;
WILLIAMS, LD ;
UGHETTO, G ;
VANDERMAREL, GA ;
VANBOOM, JH ;
RICH, A ;
WANG, AHJ .
BIOCHEMISTRY, 1990, 29 (10) :2538-2549