title: Novel Cu(II)-quinoline carboxamide complexes: structural characterization, cytotoxicity and reactivity towards 5'-GMP.
abstract: Three new ligands, N-(8-quinolyl)pyridine-2-carboxamide (HL1), N-(8-quinolyl)glycine-N'-Boc-carboxamide (HL2), N-(8-quinolyl)-L-alanine-N'-Boc-carboxamide (HL3), and their Cu(II) complexes have been synthesized. Crystallographic data reveal that complex I, [Cu(L1)(Ac)(H2O)], is penta-coordinated with a square-pyramidal geometry while complexes V [Cu(L2')(H2O)] and VI [Cu(L3')(H2O)] are tetra-coordinated to give square planar geometry. In vitro tests showed that the Cu(II) complexes with L1 (I-IV) exhibited cytotoxicity at a concentration of 10(-8) M against murine leukemia P-388 and human leukemia HL-60 cell lines, which is more potent than cisplatin. However, ligands HL2 and HL3 and their corresponding copper complexes demonstrated very weak in vitro activities towards the cell lines examined. ESMS data shows that complex I binds rapidly with 5'-GMP to form 1:1 and 2:2 adduct.
authors.affiliation: State Key Laboratory of Coordination Chemistry, Coordination Chemistry Institute, Nanjing University, 210093 Nanjing, PR China.
authors.forename: Junyong
authors.initials: J
authors.lastname: Zhang
authors.forename: Xiaokang
authors.initials: X
authors.lastname: Ke
authors.forename: Chao
authors.initials: C
authors.lastname: Tu
authors.forename: Jun
authors.initials: J
authors.lastname: Lin
authors.forename: Jian
authors.initials: J
authors.lastname: Ding
authors.forename: Liping
authors.initials: L
authors.lastname: Lin
authors.forename: Hoong-Kun
authors.initials: HK
authors.lastname: Fun
authors.forename: Xiaozeng
authors.initials: X
authors.lastname: You
authors.forename: Zijian
authors.initials: Z
authors.lastname: Guo
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D000818:Animals; D002455:Cell Division / Q000187:drug effects; D002460:Cell Line; D002470:Cell Survival / Q000187:drug effects; D003300:Copper / Q000737:chemistry*; D003460:Crystallization; D018360:Crystallography, X-Ray; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006157:Guanosine Monophosphate / Q000737:chemistry / Q000378:metabolism; D018922:HL-60 Cells; D006801:Humans; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D011804:Quinolines / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013055:Spectrophotometry, Infrared / Q000379:methods; D014407:Tumor Cells, Cultured
chemical_list: D008024:Ligands; C478658:N-(8-quinolyl)alanine-N'-tert-butoxycarbonyl-carboxamide; C478657:N-(8-quinolyl)glycine-N'-tert-butoxycarbonyl-carboxamide; D009942:Organometallic Compounds; D011804:Quinolines; D003300:Copper; D006157:Guanosine Monophosphate; D000409:Alanine; D005998:Glycine