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  • Chemistry  (2)
  • Anti-tumour agent  (1)
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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
    Electronic Resource
    Electronic Resource
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1834-1842 
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Molecular-mechanics calculations of the sexidentate coordinated complexes of the pendant arm macrocyclic hexaamines trans- (L1) and cis-6,13-dimethyl-3,4,8,11-tetraazacyclotetradecane-6,13-diamine (L2) reveal that the trans-isomer shows a preference toward small metal ions, whereas the L2 may coordinate a wider range of metal ions without significant intramolecular strain. Conformational disorder in previously reported crystal structures of complexes of L1 is interpreted, and predictions for some, as yet, unknown complexes of L2 are made.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The template reaction of {bis[(S)-2-(aminomethyl)pyrrolidine]}copper(II) with formaldehyde, nitroethane, and base in MeOH yields optically pure {1,7-bis[(S)-pyrrolidin-2-yl]-4-methyl-4-nitro-2,6-diazaheptane}- copper(II) ([Cu((S,S)-mnppm)]2+) in high yield. The same reaction with rac-2-(aminomethyl)pyrrolidine is also described. Preparative details and spectroscopic and electrochemical properties of the CuII complexes and of the free ligands are reported and compared with structural, spectroscopic and electrochemical data of the CuII complex of the unsubstituted parent ligand 1,7-bis[(S)-pyrrolidin-2-yl]-2,6-diazaheptane (ppm). The crystal structure of [Cu(ppm)]Cl ClO4 has been determined by X-ray diffraction methods.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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