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Cytotoxic di(8-quinolyl) disulfides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It has been shown that the nature of the substituent and its position in the quinoline ring markedly affects the antitumor activity and toxicity of di(8-quinolyl) disulfides. The greatest cytotoxicity in the series of methyl derivatives was shown by the 7-, 6-, and 3-isomers towards HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) tumor cells while the 2-methyl derivatives generally have no effect on these cells. High cytotoxicity was also shown (LC50 <1 µg/ml) by other 7-substituted compounds (Cl, PhO, PhS) but they also appear to be highly toxic towards normal NIH 3Y3 mouse embryonic fibroblasts. A similar trend was observed in the series of 5-substituted compounds (NH2, Cl, OMe, NO2) which were highly active towards tumor cells but were toxic to normal cells. The best selectivity was found for the 6-substituted quinolines, the 6-methoxy derivative at low concentration brought about the death of tumor cells but appeared much less toxic towards normal fibroblasts (LC50 100 µg/ml with a corresponding LD50 of 874 mg/kg ).

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006

    E. Lukevics, I. Shestakova, I. Domracheva & E. Yashchenko

  2. RTU Institute of Inorganic Chemistry, Salaspils, LV-2169, Latvia

    D. Zaruma & J. Ashaks

Authors
  1. E. Lukevics
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  2. I. Shestakova
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  3. I. Domracheva
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  4. E. Yashchenko
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  5. D. Zaruma
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  6. J. Ashaks
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__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 750–754, May 2007.

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Lukevics, E., Shestakova, I., Domracheva, I. et al. Cytotoxic di(8-quinolyl) disulfides. Chem Heterocycl Compd 43, 629–633 (2007). https://doi.org/10.1007/s10593-007-0097-7

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  • DOI: https://doi.org/10.1007/s10593-007-0097-7

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