Benzothiazole bipyridine complexes of ruthenium(II) with cytotoxic activity

C.B. Spillane, Nicholas Fletcher, Sandra Rountree, H. Van Den Berg, Severine Chanduloy, J.L. Morgan, F.R. Keene

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19 Citations (Scopus)

Abstract

A series of benzothiazole-substituted trisbipyridine ruthenium(II) analogues {[Ru(bpy)(2)(4,5'-bbtb)](2+), [Ru(bpy)(2)(5,5'-bbtb)](2+) and [Ru(bpy)(2)(5-mbtb)](2+) [bpy is 2,2'-bipyridine, bbtb is bis(benzothiazol-2-yl)-2,2'-bipyridine, 5-mbtb is 5-(benzothiazol-2-yl),5'-methyl-2,2'-bipyridine]} have been prepared and compared with the complex [Ru(bpy)(2)(4,4'-bbtb)](2+) reported previously. From the UV-vis spectral studies, substitution at the 5-position of the bpy causes the ligand-centred transitions to occur at considerably lower energy than for those with the functionality at the 4-position, while at the same time causing the emission to be effectively quenched. However, substitution at the 4-position causes the metal-to-ligand charge transfer to occur at lower energies. Fluorescent intercalator displacement studies indicate that the doubly substituted complexes displace ethidium bromide from a range of oligonucleotides, with the greater preference shown for bulge and hairpin sequences by the Lambda enantiomer. Since the complexes only show small variation in the UV-vis spectra on the introduction of calf thymus DNA and a small increase in fluorescence they do not appear to be intercalators, but appear to associate within one of the grooves. All of the reported bisbenzothiazole complexes show reasonable cytotoxicity against a range of human cancer cell lines.
Original languageEnglish
Pages (from-to)797-807
Number of pages11
JournalJournal of Biological Inorganic Chemistry
Volume12 (6)
Issue number6
DOIs
Publication statusPublished - Aug 2007

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

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    Spillane, C. B., Fletcher, N., Rountree, S., Van Den Berg, H., Chanduloy, S., Morgan, J. L., & Keene, F. R. (2007). Benzothiazole bipyridine complexes of ruthenium(II) with cytotoxic activity. Journal of Biological Inorganic Chemistry, 12 (6)(6), 797-807. https://doi.org/10.1007/s00775-007-0232-z