INVITRO ANTITUMOR-ACTIVITY OF 2 ISOMERIC CYCLOPALLADIATED COMPOUNDS DERIVED FROM BENZOYLBENZYLIDENIMINES

被引:89
作者
NAVARRORANNINGER, C [1 ]
LOPEZSOLERA, I [1 ]
PEREZ, JM [1 ]
MASAGUER, JR [1 ]
ALONSO, C [1 ]
机构
[1] UNIV AUTONOMA MADRID,CTR BIOL MOLEC,E-28049 MADRID,SPAIN
关键词
PALLADIUM; CYCLOMETALATED COMPOUNDS; ANTITUMOR;
D O I
10.1002/aoc.590070107
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The DNA thermal stabilizing effect and antitumour properties of two diastereoisomeric cyclopalladiated compounds, Pd2 [4-CH3O-C6H4N=C(COC6H5)C6H4]2(mu-OAc)2 (I and II), derived from benzoylbenzylideneimines have been studied. The atropisomers containing two acetate-bridged PdL2 units have a folded structure in boat form. The results show that both complexes interact with the DNA double helix but that compound II stabilizes the DNA more than compound I. It was also observed that the in vitro antiproliferative activity of compound II against colon (CX-1) and lung (LX-1) human tumour cells is higher than that of compound I. It is probable that the higher reactivity of compound II relative to compound I is due to the specific orientation of the benzoyl group with respect to the CO-CN chiral bond.
引用
收藏
页码:57 / 61
页数:5
相关论文
共 22 条
[1]  
BIRNBOIN HC, 1969, NUCLEIC ACIDS RES, V7, P1513
[2]   TRANSITION-METAL COMPLEXES IN CANCER CHEMOTHERAPY [J].
CLEARE, MJ .
COORDINATION CHEMISTRY REVIEWS, 1974, 12 (04) :349-405
[3]   BINDING OF CIS-DICHLORODIAMMINEPLATINUM(II) AND TRANS-DICHLORODIAMMINEPLATINUM(II) TO DNA - EVIDENCE FOR UNWINDING AND SHORTENING OF THE DOUBLE HELIX [J].
COHEN, GL ;
BAUER, WR ;
BARTON, JK ;
LIPPARD, SJ .
SCIENCE, 1979, 203 (4384) :1014-1016
[4]  
FARRELL N, 1989, TRANSITION METAL COM, P142
[5]  
FITCHTINGERSCHE.AM, 1985, BIOCHEMISTRY-US, V24, P707
[6]  
FLICK H, 1984, J IMMUNOL METHODS, V65, P167
[7]   CYCLOMETALATION OF N-(4-METHOXYPHENYL)-ALPHA-BENZOYLBENZYLIDENEAMINE WITH PALLADIUM(II) ACETATE - EVIDENCE FOR A NEW KIND OF DIASTEREOISOMERISM [J].
GARCIARUANO, JL ;
LOPEZSOLERA, I ;
MASAGUER, JR ;
NAVARRORANNINGER, C ;
RODRIGUEZ, JH ;
MARTINEZCARRERA, S .
ORGANOMETALLICS, 1992, 11 (09) :3013-3018
[8]  
GRAHAM RD, 1979, J INORG NUCL CHEM, V41, P1249
[9]   ENANTIOMERIC CISPLATIN ANALOGS - AN INVESTIGATION ON THEIR ACTIVITY TOWARDS TUMORS IN MICE [J].
GULLOTTI, M ;
PASINI, A ;
UGO, R .
INORGANICA CHIMICA ACTA-BIOINORGANIC CHEMISTRY, 1984, 91 (03) :223-227
[10]  
HERMAN TS, 1988, CANCER RES, V48, P2335