Nitrogen-containing Heterocyclic quinones: A class of potential selective antitumor agents

被引:79
作者
Garuti, Laura [1 ]
Roberti, Marinella [1 ]
Pizzirani, Daniela [1 ]
机构
[1] Univ Bologna, Dept Pharmaceut Sci, I-40126 Bologna, Italy
关键词
quinones; anticancer agents; tumor-selective toxicity; SAR; prodrugs; heterocycles; CYTOTOXICITY IN-VITRO; INDOLEQUINONE PHOSPHORAMIDATE PRODRUGS; DT-DIAPHORASE; CELL-CYCLE; BIOLOGICAL EVALUATION; NAD(P)H-QUINONE OXIDOREDUCTASE; CDC25; PHOSPHATASES; TOPOISOMERASE-II; CANCER-THERAPY; ANTIPROLIFERATIVE ACTIVITY;
D O I
10.2174/138955707780619626
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The development of prodrugs that are enzymatically activated into anticancer agents is a promising perspective in cancer therapy. Many nitrogen-containing quinoid heterocycles have been reported to show antitumor effect. The principal interest in these compounds lies on their potential to produce tumor-selective toxicity. Selectivity occurs by difference in oxygen tension between normal and tumor tissue and by levels of the required activating enzymes.
引用
收藏
页码:481 / 489
页数:9
相关论文
共 98 条
[1]  
[Anonymous], DRUG DES REV
[2]   Antitumour quinones [J].
Asche, C .
MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2005, 5 (05) :449-467
[3]   Synthesis and structure-activity relationships of 1,5-diazaanthraquinones as antitumour compounds [J].
Avendaño, C ;
Pérez, JM ;
Blanco, MD ;
de la Fuente, JA ;
Manzanaro, S ;
Vicent, MJ ;
Martín, MJ ;
Salvador-Tormo, N ;
Menéndez, JC .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (15) :3929-3932
[4]   Indolequinone antitumor agents: Relationship between quinone structure and rate of metabolism by recombinant human NQO1 [J].
Beall, HD ;
Hudnott, AR ;
Winski, S ;
Siegel, D ;
Swann, E ;
Ross, D ;
Moody, CJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (05) :545-548
[5]   Mechanisms of action of quinone-containing alkylating agents I: NQO1-directed drug development [J].
Beall, HD ;
Winski, SL .
FRONTIERS IN BIOSCIENCE-LANDMARK, 2000, 5 :D639-D648
[6]   Indolequinone antitumor agents:: Correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity [J].
Beall, HD ;
Winski, S ;
Swann, E ;
Hudnott, AR ;
Cotterill, AS ;
O'Sullivan, N ;
Green, SJ ;
Bien, R ;
Siegel, D ;
Ross, D ;
Moody, CJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) :4755-4766
[7]   BBR 2778, an aza-anthracenedione endowed with preclinical anticancer activity and lack of delayed cardiotoxicity [J].
Beggiolin, G ;
Crippa, L ;
Menta, E ;
Manzotti, C ;
Cavalletti, E ;
Pezzoni, G ;
Torriani, D ;
Randisi, E ;
Cavagnoli, R ;
Sala, F ;
Giuliani, FC ;
Spinelli, S .
TUMORI, 2001, 87 (06) :407-416
[8]   The oxidative mechanism of action of ortho-quinone inhibitors of protein-tyrosine phosphatase α is mediated by hydrogen peroxide [J].
Bova, MP ;
Mattson, MN ;
Vasile, S ;
Tam, D ;
Holsinger, L ;
Bremer, M ;
Hui, T ;
McMahon, G ;
Rice, A ;
Fukuto, JM .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2004, 429 (01) :30-41
[9]   Inhibition of human tumor cell growth in vivo by an orally bioavailable inhibitor of CDC25 phosphatases [J].
Brezak, MC ;
Quaranta, M ;
Contour-Galcera, MO ;
Lavergne, O ;
Mondesert, O ;
Auvray, P ;
Kasprzyk, PG ;
Prevost, GP ;
Ducommun, B .
MOLECULAR CANCER THERAPEUTICS, 2005, 4 (09) :1378-1387
[10]   Redox regulation of Cdc25B by cell-active quinolinediones [J].
Brisson, M ;
Nguyen, T ;
Wipf, P ;
Joo, B ;
Day, BW ;
Skoko, JS ;
Schreiber, EM ;
Foster, C ;
Bansal, P ;
Lazo, JS .
MOLECULAR PHARMACOLOGY, 2005, 68 (06) :1810-1820