COPPER(II) BIPYRIDYL AND IMINOPYRIDYL ANALOGS OF STREPTONIGRIN

被引:10
作者
LONG, GV [1 ]
HARDING, MM [1 ]
TURNER, P [1 ]
HAMBLEY, TW [1 ]
机构
[1] UNIV SYDNEY,SCH CHEM,SYDNEY,NSW 2006,AUSTRALIA
来源
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS | 1995年 / 23期
关键词
D O I
10.1039/dt9950003905
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The crystal structures of (3-amino-6,6'-dimethyl-2,2'-bipyridine)dichlorocopper(II) [CuL(1)Cl(2)], and aqua[3-imido-6-(methoxycarbonyl)-2,2'-bipryidine-6'-carboxylato]copper(II), [CuL(3)(H2O)], have been determined. The complex [CuL(1)Cl(2)] crystallizes in space group Pnma with a=19.434(3), b=7.427(2). c=9.403(1) Angstrom and Z=4. The structure has been refined to a final R value of 0.057 based on 680 independent reflections. The copper(ii) centre exhibits tetrahedral co-ordination to the bipyridyl nitrogens of L(1) and two chlorine atoms. Crystals of [CuL(3)(H2O)] were grown from a solution of 3-amino-6,6'-bis(methoxycarbonyl)-2,2'-bypyridine (L(2)) and excess Cu-II The complex crystallizes in space group P2(1)/n with a=3.724(2), b=14,375(3), c=22.953(5) Angstrom, beta=90.72(3)degrees and Z=4. The structure has been refined to a final R value of 0.061 based on 944 independent reflections. The Cu-II centre is square planar with a slight tetrahedral deformation, and co-ordinates to an imino nitrogen. adjacent pyridyl nitrogen, carboxylate oxygen and a water molecule. The implications of these results on the types of complexes formed by streptonigrin are discussed.
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页码:3905 / 3910
页数:6
相关论文
共 38 条
[1]   NADPH CYTOCHROME-P-450 REDUCTASE ACTIVATION OF QUINONE ANTI-CANCER AGENTS TO FREE-RADICALS [J].
BACHUR, NR ;
GORDON, SL ;
GEE, MV ;
KON, H .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (02) :954-957
[2]  
BACHUR NR, 1978, CANCER RES, V38, P1745
[3]   STREPTONIGRIN AND LAVENDAMYCIN PARTIAL STRUCTURES - PROBES FOR THE MINIMUM, POTENT PHARMACOPHORE OF STREPTONIGRIN, LAVENDAMYCIN, AND SYNTHETIC QUINOLINE-5,8-DIONES [J].
BOGER, DL ;
YASUDA, M ;
MITSCHER, LA ;
DRAKE, SD ;
KITOS, PA ;
THOMPSON, SC .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1918-1928
[4]  
CHIRIGOS MA, 1973, CANCER CHEMOTH REP 1, V57, P305
[5]   EFFECTS OF STREPTONIGRIN ON CULTURED HUMAN LEUKOCYTES [J].
COHEN, MM ;
CRAIG, AP ;
SHAW, MW .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1963, 50 (01) :16-&
[6]   MECHANISM OF DEGRADATION OF DNA BY STREPTONIGRIN [J].
CONE, R ;
HASAN, SK ;
LOWN, JW ;
MORGAN, AR .
CANADIAN JOURNAL OF BIOCHEMISTRY, 1976, 54 (03) :219-223
[7]   MODEL DEHYDROGENASE REACTIONS - ZINC ION CATALYZED REDUCTION OF CHELATING ALDEHYDES BY N-PROPYL-1,4-DIHYDRONICOTINAMIDES AND BOROHYDRIDE [J].
CREIGHTON, DJ ;
HAJDU, J ;
SIGMAN, DS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (15) :4619-4625
[8]   FREE-RADICAL MODES OF CYTOTOXICITY OF ADRIAMYCIN(R) AND STREPTONIGRIN [J].
DEGRAFF, W ;
HAHN, SM ;
MITCHELL, JB ;
KRISHNA, MC .
BIOCHEMICAL PHARMACOLOGY, 1994, 48 (07) :1427-1435
[9]   THE NEGATIVE CHARGE OF ALKYL PHOSPHATE DIESTERS AND THE SLOW-GAITED HYDROLYSIS OF RNA AND DNA - CATALYSIS OF RNA HYDROLYSIS THROUGH METAL-ION LIGATION TO THE ESTER GREATER-THAN-PO2- MOIETY [J].
DEMPCY, RO ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (10) :4511-4512
[10]   METAL-ION PROMOTED HYDROXIDE ION AND WATER CATALYZED-HYDROLYSIS OF AMIDES - EFFECTS OF THE ACYL GROUP AND THE LEAVING GROUP [J].
FIFE, TH ;
BEMBI, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11358-11363