Toward the design of novel polynuclear platinum antitumor complexes: a polydentate ligand system based on dipyridylamine and 1,3,5-trimethylenebenzene.
A novel hexadentate ligand, N,N,N',N',N",N"-hexa(2-pyridyl)-1,3,5-tris(aminomethyl)benzene (L), was designed and synthesized. The X-ray structure analysis reveals that the three dipyridylamine (DPA) groups of L are almost perpendicular to the central trimethylenebenzene, and two of them are spacially close to each other while the third one is further apart. The trinuclear Pt(II) complexes [Pt(3)LCl(6)] (1) and [Pt(3)L(CBDCA)(3)] (2) (where CBDCA represents cyclobutane dicarboxylic acid) were prepared and fully characterized by IR, NMR, and ESMS spectroscopy. A mononuclear complex, [PtL(CBDCA)] (3), was also prepared and structurally characterized, which suggests that controlled formation of mono-, di-, and trinuclear complexes with L is possible. Spectroscopic data showed that complexes 2 and 3 are able to bind to calf thymus DNA and their CBDCA group can be readily replaced by thiourea.
Tu
Chao
C
State Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, Nanjing University, 210093 Nanjing, P. R. China.
Lin
Jun
J
Shao
Ying
Y
Guo
Zijian
Z
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000737:chemistry*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001555:Benzene Derivatives / Q000737:chemistry*; D002417:Cattle; D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D009944:Organoplatinum Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
C482494:1,3,5-trimethylenebenzene; D000970:Antineoplastic Agents; D001555:Benzene Derivatives; D008024:Ligands; D009944:Organoplatinum Compounds; D015082:2,2'-Dipyridyl; D004247:DNA; C048062:2,2'-dipyridylamine