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  • 2-n-heptyl-4-hydroxyquinoline-N-oxide  (1)
  • Anti-tumour agent  (1)
  • (Melanoma cell)
  • Springer  (2)
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  • 1
    ISSN: 1432-1327
    Keywords: Key words Crystal structure ; Iron chelators ; Anti-tumour agent
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract  Previous studies have demonstrated that 2-hydroxy-1-naphthaldehyde isonicotinoyl hydrazone (NIH) and several other aroylhydrazone chelators possess anti-neoplastic activity due to their ability to bind intracellular iron. In this study we have examined the structure and properties of NIH and its FeIII complex in order to obtain further insight into its anti-tumour activity. Two tridentate NIH ligands deprotonate upon coordination to FeIII in a meridional fashion to form a distorted octahedral, high-spin complex. Solution electrochemistry of [Fe(NIH–H)2]+ shows that the trivalent oxidation state is dominant over a wide potential range and that the FeII analogue is not a stable form of this complex. The fact that [Fe(NIH–H)2]+ cannot cycle between the FeII and FeIII states suggests that the production of toxic free-radical species, e.g. OH . or O2 . –, is not part of this ligand's cytotoxic action. This suggestion is supported by cell culture experiments demonstrating that the addition of FeIII to NIH prevents its anti-proliferative effect. The chemistry of this chelator and its FeIII complex are discussed in the context of understanding its anti-tumour activity.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1432-072X
    Keywords: Rhodobacter capsulatus ; Nitrate reduction ; Auxiliary electron transport ; Myxothiazol ; 2-n-heptyl-4-hydroxyquinoline-N-oxide ; Ubiquinone pool
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The effects of various electron transport inhibitors upon the rates of reduction NO 3 - , dimethyl sulphoxide (DMSO) and N2O in anaerobic suspensions of Rhodobacter capsulatus have been studied. A new method for the determination of the rates of reduction of these auxiliary oxidants in intact cells is presented, based on the proportionality observed between the concentration of oxidant and the duration of the electrochromic carotenoid bandshift. For NO 3 - and N2O good agreement was found between rates of reduction determined using electrodes and those determined by the electrochromic method. Myxothiazol and antimycin A had no effect on the rates of reduction of NO 3 - and DMSO suggesting that the cytochrome b/c 1complex is not involved in electron transport to these oxidants. 2-n-heptyl-4-hydroxyquinoline-N-oxide (HOQNO) inhibited at two sites, one within the cytochrome b/c 1complex and the other on the nitrate reducing pathay, but had no effect on electron transport to N2O or DMSO. In both intact cells and cell free extracts, HOQNO had no effect on the nitrate dependent re-oxidation of reduced methylviologen (MVH2), a direct electron donor to nitrate reductase. Our data are consistent with a branch point for the auxiliary electron transport pathways at the level of the ubiquinone pool.
    Type of Medium: Electronic Resource
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