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Synthesis and cytotoxicity of methyl-substituted 8-quinolineselenolates of ruthenium, rhodium, osmium, and iridium

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Chemistry of Heterocyclic Compounds Aims and scope

A series of 2-methyl, 4-methyl, and 2,4-dimethyl-8-quinolineselenolates of ruthenium, rhodium, osmium, and iridium has been synthesized and their cytotoxicity towards HT-1080 (human fibrosarcoma) and MG-22A (mouse hepatoma) tumor cells studied. It was found that all of the osmium complexes had a high cytotoxicity towards both cell lines. Their toxicity towards the normal mouse embryonic fibroblasts NIH-3T3 depends on the position and number of methyl groups in the quinoline ring and decreases in the order 2-Me > 4-Me > 2,4-Me2. The greatest selectivity in cytoxic activity is noted for iridium 4-methyl-8-quinolineselenolate and ruthenium 2-methyl-8-quinolineselenolate.

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References

  1. V. Brabec, J. Kasparkova, in: M. Gielen and E. R. T. Tiekink (editors), Metallotherapeutic Drugs and Metal-Based Diagnostic Agents, J. Wiley and Sons Ltd., Chichester (2005), p. 489.

    Chapter  Google Scholar 

  2. P. C. Bruijnincx and P. J. Sadler, Current Opinion in Chemical Biology, 12, 197 (2008).

    Article  CAS  Google Scholar 

  3. O. Lentzen, C. Mouchenon, and A. Kirsch-De Mesmaeker, in: M. Gielen and E. R. T. Tiekink (editors), Metallotherapeutic Drugs and Metal-Based Diagnostic Agents, J. Wiley and Sons Ltd., Chichester (2005), p. 359.

    Chapter  Google Scholar 

  4. P. J. Dyson and G. Sava, Dalton Trans., 1929 (2006).

  5. I. Kostova, Curr. Med. Chem., 13, 1085 (2006).

    Article  CAS  Google Scholar 

  6. H. A. Wee and P. J. Dyson, Eur. J. Inorg. Chem., 4003 (2006).

  7. E. Meggers, G. E. Atilla-Gokcumen, H. Bregman, J. Maksimoska, S. P. Mulcahy, N. Pagano, and D. S. Williams, Synlett, 1177 (2007).

  8. S. S. Karki, S. Thota, S. Y. Darj, J. Balzarini, and E. De Clercq, Bioorg. Med. Chem., 15, 6632 (2007).

    Article  CAS  Google Scholar 

  9. C. A. Vock, W. H. Ang, C. Scolaro, A. D. Phillips, L. Lagopoulos, L. Juillerat-Jeanneret, G. Sava, R. Scopelliti, and P. J. Dyson, J. Med. Chem., 50, 2166 (2007).

    Article  CAS  Google Scholar 

  10. M. Auzias, B. Therrien, G. Süss-Fink, P. Štěpnička, H. A. Wee, and P. J. Dyson, Inorg. Chem., 47, 578 (2008).

    Article  CAS  Google Scholar 

  11. I. Bratsos, A. Bergamo, G. Sava, T. Gianferrara, E. Zangrando, and E. Alessio, J. Inorg. Biochem., 102, 606 (2008).

    Article  CAS  Google Scholar 

  12. I. Bratsos, S. Jedner, A. Bergamo, G. Sava, T. Gianferrara, E. Zangrando, and E. Alessio, J. Inorg. Biochem., 102, 1120 (2008).

    Article  CAS  Google Scholar 

  13. S. J. Dougan, A. Habtemariam, S. E. McHale, S. Parsons, and P. J. Sadler, Proc. Natl. Acad. Sci. USA, 105, 11628 (2008).

    Article  CAS  Google Scholar 

  14. B. Dutta, C. Scolaro, R. Scopelliti, P. J. Dyson, and K. Severin, Organometallics, 27, 1355 (2008).

    Article  CAS  Google Scholar 

  15. A. Garza-Ortiz, P. V. Maheswari, M. Siegler, A. L. Spek, and J. Reedijk, Inorg. Chem., 47, 6964 (2008).

    Article  CAS  Google Scholar 

  16. M. Gras, B. Therrien, G. Süss-Fink, P. Štěpnička, A. K. Renfrew, and P. J. Dyson, J. Organomet. Chem., 693, 3419 (2008).

    Article  CAS  Google Scholar 

  17. M.-G. Mendoza-Ferri, C. G. Hartinger, R. E. Eichinger, N. Stolyarova, K. Severin, M. A. Jakupec, A. A. Nazarov, and B. K. Keppler, Organometallics, 27, 2405 (2008).

    Article  CAS  Google Scholar 

  18. C. Tan, J. Liu, H. Li, W. Zheng, S. Shi, L. Chen, and L. Ji, J. Inorg. Biochem., 102, 347 (2008).

    Article  CAS  Google Scholar 

  19. C. Tan, J. Liu, L. Chen, S. Shi, and L. Ji, J. Inorg. Biochem, 102, 1644 (2008).

    Article  CAS  Google Scholar 

  20. C. A. Vock, A. K. Renfrew, R. Scopelliti, L. Juillerat-Jeanneret, and P. J. Dyson, Eur. J. Inorg. Chem., 1661 (2008).

  21. F. Schmitt, P. Govindaswamy, G. Süss-Fink, W. H. Ang, P. D. Dyson, L. Juillerat-Jeanneret, and B. Therrien, J. Med. Chem., 51, 1811 (2008).

    Article  CAS  Google Scholar 

  22. A. Dorcier, W. H. Ang, S. Bolaño, L. Gonsalvi, L. Juillerat-Jeanneret, G. Laurenzy, M. Peruzzini, A. D. Phillips, F. Zanobini, and P. J. Dyson, Organometallics, 27, 4090 (2006).

    Article  CAS  Google Scholar 

  23. F. P. Pruchnik in: M. Gielen and E. R. T. Tiekink (editors), Metallotherapeutic Drugs and Metal-Based Diagnostic Agents, J. Wiley and Sons Ltd., Chichester (2005), p. 379.

    Chapter  Google Scholar 

  24. D. A. Medvetz, K. D. Stakleff, T. Schreiber, P. D. Custer, K. Hindi, M. J. Panzner, D. D. Blanko, M. J. Tashner, C. A. Tessier, and W. J. Youngs, J. Med. Chem., 50, 1703 (2007).

    Article  CAS  Google Scholar 

  25. N. J. Wheate, C. R. Brodie, J. G. Collins, S. Kemp, and J. R. Aldrich-Wright, Mini-Rev. Med. Chem., 7, 627 (2007).

    Article  CAS  Google Scholar 

  26. M. Harlos, I. Ott, R. Gust, H. Alborzinia, S. Wölfe, A. Kromm, and W. S. Sheldrick, J. Med. Chem., 51, 3924 (2008).

    Article  CAS  Google Scholar 

  27. A. F. A. Peacock, A. Habtemariam, S. A. Moggach, A. Prescimone, S. Parsons, and P. J. Sadler, Inorg. Chem., 46, 4049 (2007).

    Article  CAS  Google Scholar 

  28. A. F. A. Peacock, M. Melchart, R. J. Deeth, A. Habtemariam, S. Parsons, and P. J. Sadler, Chem. Eur. J., 13, 2601 (2007).

    Article  CAS  Google Scholar 

  29. A. F. A. Peacock, S. Parsons, and P. J. Sadler, J. Am. Chem. Soc., 129, 3348 (2007).

    Article  CAS  Google Scholar 

  30. H. Kostrhunova, J. Florian, O. Novakova, A. F. A. Peacock, P. J. Sadler, and V. Brabec, J. Med. Chem., 51, 3635 (2008).

    Article  CAS  Google Scholar 

  31. I. N. Stepanenko, A. A. Krokhin, R. O. John, A. Roller, V. B. Arion, M. A. Jakupec, and B. K. Keppler, Inorg. Chem., 47, 7338 (2008).

    Article  CAS  Google Scholar 

  32. E. Lukevics, I. Shestakova, I. Domracheva, A. Nesterova, D. Zaruma, and J. Ashaks, Khim. Geterotsikl. Soedin., 870 (2006). [Chem. Heterocycl. Comp., 42, 761 (2006)].

    Google Scholar 

  33. E. Lukevics, I. Shestakova, I. Domracheva, E. Yashchenko, D. Zaruma, and J. Ashaks, Khim. Geterotsikl. Soedin., 755 (2007). [Chem. Heterocycl. Comp., 43, 634 (2007)].

    Google Scholar 

  34. E. Lukevics, D. Zaruma, J. Ashaks, I. Shestakova, I. Domracheva, A. Gulbe, and V. Bridane, Khim. Geterotsikl. Soedin., 711 (2008). [Chem. Heterocycl. Comp., 44, 559 (2008)].

    Google Scholar 

  35. J. Ashaks, Yu. Bankovskii, D. Zaruma, I. Shestakova, I. Domracheva, A. Nesterova, and E. Lukevics, Khim. Geterotsikl. Soedin., 905 (2004). [Chem. Heterocycl. Comp., 40, 776 (2004)].

    Google Scholar 

  36. M. A. Scharwitz, I. Ott, R. Gust, A. Kromm, and W. S. Sheldrick, J. Inorg. Biochem., 102, 1623 (2008).

    Article  CAS  Google Scholar 

  37. K. El-Bayoumy, Cancer Res., 45, 3631 (1985).

    CAS  Google Scholar 

  38. B. S. Reddy, T. Tanaka, and B. Simi, J. Nat. Cancer. Inst., 75, 791 (1985).

    CAS  Google Scholar 

  39. E. Lukevics, P. Arsenyan, K. Rubina, I. Shestakova, I. Domracheva, A. Nesterova, J. Popelis, and O. Pudova, Appl. Organomet. Chem., 16, 235 (2000).

    Article  CAS  Google Scholar 

  40. E. Lukevics, P. Arsenyan, I. Shestakova, I. Domracheva, I. Kanepe, S. Belyakov, J. Popelis, and O. Pudova, Appl. Organomet. Chem., 16, 228 (2000).

    Article  CAS  Google Scholar 

  41. S. W. May, Expert Opinion on Investigational Drugs, 11, 1261 (2002).

    Article  CAS  Google Scholar 

  42. M. Koketsu and H. Ishihara, Curr. Org. Chem., 7, 175 (2003).

    Article  CAS  Google Scholar 

  43. A. J. Duffield-Lillico, I. Shureiqi, and S. M. Lippman, J. Nat. Cancer Inst., 96, 1645 (2004).

    Article  CAS  Google Scholar 

  44. C. W. Nogueira, G. Zeni, and J. B. T. Rocha, Chem. Rev., 104, 6255 (2004).

    Article  CAS  Google Scholar 

  45. M. Soriano-Garcia, Curr. Med. Chem., 11, 1657 (2004).

    CAS  Google Scholar 

  46. P. D. Whanger, in: A. S. Award and P. G. Bradford (editors), Nutrition and Cancer Prevention, CRC, Taylor and Francis Group. Boca Raton, London, New York (2006), p. 189.

    Google Scholar 

  47. L. Letavayová, V. Vlčková, and J. Brozmanová, Toxicology, 227, 1 (2006).

    Article  CAS  Google Scholar 

  48. G-X. Li, H. Hu, C. Jiang, T. Schuster, and J. Lu, Int. J. Cancer, 120, 2034 (2007).

    Article  CAS  Google Scholar 

  49. W. M. El-Sayed, T. Aboul-Fadl, J. C. Roberts, J. G. Lamb, and M. R. Franklin, Toxicology in Vitro, 21, 157 (2007).

    Article  CAS  Google Scholar 

  50. W. Mól, M. Matyja, B. Filip, J. Wietrzyk, and S. Boryczka, Bioorg. Med. Chem., 16, 8136 (2008).

    Article  CAS  Google Scholar 

  51. E. Lukevics, I. Shestakova, I. Domracheva, A. Nesterova, J. Ashaks, and D. Zaruma, Khim. Geterotsikl. Soedin., 59 (2006). [Chem. Heterocycl. Comp., 42, 53 (2006)].

    Google Scholar 

  52. Guidance Document on Using in vitro Data to Estimate in vivo Starting Doses for Acute Toxicity, National Institute of Health, US Dept. of Health and Human Services (2001), p. 12.

  53. G. Veinberg, M. Vorona, I. Shestakova, I. Kanepe, O. Zharkova, R. Mezapuke, I. Turovskis, I. Kalvinsh, and E. Lukevics, Bioorg. Med. Chem., 8, 1033 (2000).

    Article  CAS  Google Scholar 

  54. E. Lukevics, L. Ignatovich, I. Sleiksha, V. Muravenko, I. Shestakova, S. Belyakov, and J. Popelis, Appl. Organometal. Chem., 20, 454 (2006).

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

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

  2. Inorganic Chemistry Institute of the Riga Technical University, Salaspils, LV-2169, Latvia

    D. Zaruma & J. Ashaks

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  1. E. Lukevics
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  2. D. Zaruma
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  4. I. Shestakova
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  5. I. Domracheva
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  6. V. Bridane
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  7. E. Yashchenko
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Correspondence to E. Lukevics.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 230–236, February, 2009.

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Lukevics, E., Zaruma, D., Ashaks, J. et al. Synthesis and cytotoxicity of methyl-substituted 8-quinolineselenolates of ruthenium, rhodium, osmium, and iridium. Chem Heterocycl Comp 45, 182–187 (2009). https://doi.org/10.1007/s10593-009-0248-0

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