Natural and synthetic acridines/acridones as antitumor agents: their biological activities and methods of synthesis

被引:140
作者
Cholewinski, Grzegorz [1 ]
Dzierzbicka, Krystyna [1 ]
Kolodziejczyk, Aleksander M. [1 ]
机构
[1] Gdansk Univ Technol, Dept Organ Chem, PL-80233 Gdansk, Poland
关键词
acridine/acridone analogs; synthesis; biological activity; anticancer activity; RESISTANT CELL-LINES; 9-SUBSTITUTED ACRIDINE-DERIVATIVES; TELOMERE TARGETING AGENTS; ACRIDONE DERIVATIVES; CYTOTOXIC ACTIVITY; ANTICANCER AGENTS; TUMOR-CELLS; DNA-BINDING; TRIAZOLOACRIDONE C-1305; PRECLINICAL EVALUATION;
D O I
10.1016/S1734-1140(11)70499-6
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
Acridine derivatives constitute a class of compounds that are being intensively studied as potential anticancer drugs. Acridines are well-known for their high cytotoxic activity; however, their clinical application is limited or even excluded because of side effects. Numerous synthetic methods are focused on the preparation of target acridine skeletons or modifications of naturally occurring compounds, such as acridone alkaloids, that exhibit promising anticancer activities. They have been examined in vitro and in vivo to test their importance for cancer treatment and to establish the mechanism of action at both the molecular and cellular level, which is necessary for the optimization of their properties so that they are suitable in chemotherapy. In this article, we review natural and synthetic acridine/acridone analogs, their application as anticancer drugs and methods for their preparation.
引用
收藏
页码:305 / 336
页数:32
相关论文
共 105 条
[1]   Crystal structure of 9-amino-N-[2-(4-morpholinyl)ethyl]-4-acridinecarboxamide bound to d(CGTACG)2:: implications for structure-activity relationships of acridinecarboxamide topoisomerase poisons [J].
Adams, A ;
Guss, JM ;
Denny, WA ;
Wakelin, LPG .
NUCLEIC ACIDS RESEARCH, 2002, 30 (03) :719-725
[2]  
Afloroaei C, 2004, REV CHIM-BUCHAREST, V55, P536
[3]   The antiviral agent 5-chloro-1,3-dihydroxyacridone interferes with assembly and maturation of herpes simplex virus [J].
Akanitapichat, P ;
Bastow, KF .
ANTIVIRAL RESEARCH, 2002, 53 (02) :113-126
[4]   Synthesis of 3′-3′-linked pyrimidine oligonucleotides containing an acridine moiety for alternate strand triple helix formation [J].
Amato, J ;
Galeone, A ;
Oliviero, G ;
Mayol, L ;
Piccialli, G ;
Varra, M .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (11) :2331-2336
[5]   Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum [J].
Anderson, MO ;
Sherrill, J ;
Madrid, PB ;
Liou, AP ;
Weisman, JL ;
DeRisi, JL ;
Guy, RK .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (02) :334-343
[6]  
[Anonymous], 1966, EDWARD ARNOLD
[7]   Rational design, synthesis, and biological evaluation of bis(pyrimido[5,6,1-de]acridines) and bis(pyrazolo[3,4,5-kl]acridine-5-carboxamides) as new anticancer agents [J].
Antonini, I ;
Polucci, P ;
Magnano, A ;
Sparapani, S ;
Martelli, S .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (21) :5244-5250
[8]   2,3-dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione derivatives, a class of cytotoxic agents active on multidrug-resistant cell lines:: Synthesis, biological evaluation, and structure-activity relationships [J].
Antonini, I ;
Polucci, P ;
Kelland, LR ;
Menta, E ;
Pescalli, N ;
Martelli, S .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (14) :2535-2541
[9]   Design, synthesis, and biological properties of new bis(acridine-4-carboxamides) as anticancer agents [J].
Antonini, I ;
Polucci, P ;
Magnano, A ;
Gatto, B ;
Palumbo, M ;
Menta, E ;
Pescalli, N ;
Martelli, S .
JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (14) :3109-3115
[10]  
Antonini I, 2002, CURR MED CHEM, V9, P1701