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Synthesis and studies of acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione as potential antitumor agents

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Abstract

Nucleophilic substitution of a chlorine atom in 4,5 dichloro-1,2-dithiole-3-thione with per-O-acetyl-1-mercaptho derivatives of d-glucose, d-galactose, d-mannose, d-xylose, l-arabinose, and d-maltose gave six new acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione. These thioglycosides were shown to possess cancer preventive activity on the models of JB6 Cl41 P+ mouse epidermal cells and THP-1 human leukemia cells in soft agar, as well as to inhibit the AP-1-dependent transcriptional activity in JB6 Cl41 luc-AP-1 cells, which suggests the possibility of using the new compounds as potential cancer preventive drugs.

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References

  1. R. Marković, A. Rašović, in Comprehensive Heterocyclic Chemistry III, Ed. J. A. Joule, Elsevier, Oxford, 2008, Vol. 4, pp. 892–954.

  2. V. A. Ogurtsov, O. A. Rakitin, Russ. Chem. Rev., 2012, 81, 1146.

    Article  Google Scholar 

  3. C. T. Pedersen, Sulfur Rep., 1995, 16, 173.

    Article  CAS  Google Scholar 

  4. S. Archer, Ann. Rev. Pharm. Toxicol., 1985, 25, 485.

    Article  CAS  Google Scholar 

  5. G. J. Kelloff, C. W. Boone, J. A. Crowell, V. E. Steele, R. Lubet, C. C. Sigman, Cancer Epidemiol. Biomarkers Prev., 1994, 3, 85.

    CAS  PubMed  Google Scholar 

  6. T. W. Kensler, X. He, M. Otieno, P. A. Egner, L. P. Jacobson, B. Chen, J. S. Wang, Y. R. Zhu, B. C. Zhang, J. B. Wang, Y. Wu, Q. N. Zhang, G. S. Qian, S. Y. Kuang, X. Fang, Y. F. Li, L. Y. Yu, H. J. Prochaska, N. E. Davidson, G. B. Gordon, M. B. Gorman, A. Zarba, C. Enger, A. Muñoz, K. J. Helzlsouer, J. D. Groopman, Cancer Epidemiol. Biomarkers Prev., 1998, 7, 127.

    CAS  PubMed  Google Scholar 

  7. H. J. Prochaska, M. J. DeLong, P. Talalay, Proc. Natl. Acad. Sci. USA, 1985, 82, 8232.

    Article  CAS  Google Scholar 

  8. L. Jirousec, J. Starka Naturwissenschaften, 1958, 45, 386.

    Article  Google Scholar 

  9. M. Kenig, C. Reading, J. Antibiot., 1979, 32, 549.

    Article  CAS  Google Scholar 

  10. D. R. Appleton, B. R. Copp, Tetrahedron Lett., 2003, 44, 8963.

    Article  CAS  Google Scholar 

  11. S. Homhual, H. J. Zhang, N. Bunyapraphatsara, T. P. Kondratyuk, B. D. Santarsiero, A. D. Mesecar, A. Herunsalee, W. Chaukul, J. M. Pezzuto, H. S. Fong, Planta Med., 2006, 72, 255.

    Article  CAS  Google Scholar 

  12. X. Y. Huang, Q. Wang, H. L. Liu, Y. Zhang, G. R. Xin, X. Shen, M. L. Dong, Y. W. Guo, Phytochemistry, 2009, 70, 2096.

    Article  CAS  Google Scholar 

  13. M. I. Ansari, M. M. Khan, M. Saquib, S. Khatoon, M. K. Hussain, Future Med. Chem., 2018, 10, 1241.

    Article  CAS  Google Scholar 

  14. Y. B. Cui, S. S. Ma, C. Y. Zhang, D. P. Li, Bo Yang, P. Ju Lv, Qu Xing, T. Huang, G. L. Yang, W. Cao, F. X. Guan, Behav. Brain Res., 2018, 336, 219.

    Article  CAS  Google Scholar 

  15. M. K. Kwak, P. A. Egner, P. M. Dolan, M. Ramos-Gomez, J. D. Groopman, K. Itoh, M. Yamamoto, T. W. Kensler, Mutat. Res., 2001, 480, 305.

    Article  Google Scholar 

  16. C. H. Switzer, R. Y. Cheng, L. A. Ridnour, M. C. Murray, V. Tazzari, A. Sparatore, P. Del Soldato, H. B. Hines, S. A. Glynn, S. Ambs, D. A. Wink, Cancer Res., 2012, 72, 2394.

    Article  CAS  Google Scholar 

  17. V. A. Ogurtsov, Yu. V. Karpychev, A. A. Smolentsev, O. A. Rakitin, Phosphorus, Sulfur Silicon Relat. Elem., 2011, 186, 1201.

    Article  CAS  Google Scholar 

  18. V. A. Ogurtsov, O. A. Rakitin, C. W. Rees, A. A. Smolentsev, Mendeleev Commun., 2003, 13, 50.

    Article  Google Scholar 

  19. V. A. Ogurtsov, O. A. Rakitin, C. W. Rees, A. A. Smolentsev, P. A. Belyakov, D. G. Golovanov, K. A. Lyssenko, Org. Lett., 2005, 7, 791.

    Article  CAS  Google Scholar 

  20. V. A. Ogurtsov, O. A. Rakitin, C. W. Rees, A. A. Smolentsev, Mendeleev Commun., 2005, 15, 55.

    Article  Google Scholar 

  21. A. A. Smolentsev, Ph. D. Thesis (Chem.), Moscow, N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 2005 (in Russian).

    Google Scholar 

  22. S. G. Polonik, N. G. Prokof’eva, I. G. Agafonova, N. I. Uvarova, Pharm. Chem. J., 2003, 37, 397.

    Article  CAS  Google Scholar 

  23. T. Fujihira, M. Chida, H. Kamijo, T. Takido, M. Seno, J. Carbohydr. Chem., 2002, 21, 287.

    Article  CAS  Google Scholar 

  24. J. A. Barltrop, T. C. Owen, A. H. Cory, J. G. Cory, Bioorg. Med. Chem. Lett., 1991, 11, 611.

    Article  Google Scholar 

  25. N. H. Colburn, B. F. Former, K. A. Nelson, S. H. Yuspa, Nature, 1979, 281, 589.

    Article  CAS  Google Scholar 

  26. Z. Dong, M. J. Birrer, R. G. Watts, L. M. Matrisian, N. H. Colburn, Proc. Natl. Acad. Sci. USA, 1994, 91, 609.

    Article  CAS  Google Scholar 

  27. Z. Dong, R. G. Watts, Y. Sun, N. H. Colburn, Int. J. Oncol., 1995, 7, 359.

    CAS  PubMed  Google Scholar 

  28. N. Ye, Y. Ding, C. Wild, Q. Shen, J. Zhou, J. Med. Chem., 2014, 57, 6930.

    Article  CAS  Google Scholar 

  29. S. Balasubramanian, R. L. Eckert, J. Biol. Chem., 2007, 282, 6707.

    Article  CAS  Google Scholar 

  30. J. Lee, C. Park, W. Kim, Y. H. Hwan, K. Jeong, C. Yang, Bull. Korean Chem. Soc., 2006, 27, 535.

    Article  CAS  Google Scholar 

  31. S. N. Fedorov, S. A. Dyshlovoy, M. M. Monastyrnaya, L. K. Shubina, E. V. Leychenko, E. P. Kozlovskaya, J. O. Jin, J. Y. Kwak, A. M. Bode, Z. Dong, V. A. Stonik, Toxicon., 2010, 55, 811.

    Article  CAS  Google Scholar 

  32. S. A. Dyshlovoy, S. N. Fedorov, A. I. Kalinovsky, L. K. Shubina, C. Bokemeyer, V. A. Stonik, F. Honecker, Mar. Drugs, 2012, 10, 1212.

    Article  CAS  Google Scholar 

  33. K. P. Devkota, R. Ratnayake, N. H. Colburn, J. A. Wilson, C. J. Henrich, J. B. McMahon, J. A. Beutler, J. Nat. Prod., 2011, 74, 374.

    Article  CAS  Google Scholar 

  34. S. A. Dyshlovoy, K. M. Tabakmakher, J. Hauschild, R. K. Shchekaleva, K. Otte, A. G. Guzii, T. N. Makarieva, E. K. Kudryashova, S. N. Fedorov, L. K. Shubina, C. Bokemeyer, F. Honecker, V. A. Stonik, G. von Amsberg, Mar. Drugs, 2016, 14, 133.

    Article  Google Scholar 

  35. T. Diyabalanage, R. Ratnayake, J. A. Wilson, C. J. Henrich, J. A. Beutler, N. H. Colburn, J. B. McMahon, K. R. Gustafson, Bioorg. Med. Chem. Lett., 2011, 21, 4397.

    Article  CAS  Google Scholar 

  36. F. Boberg, Justus Liebigs. Ann. Chem., 1964, 679, 109.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. G. B. Elyakov Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, 159 prosp. 100 letiya Vladivostoka, 690022, Vladivostok, Russian Federation

    S. N. Fedorov, A. S. Kuzmich, Yu. E. Sabutskii, A. G. Guzii, R. S. Popov & S. G. Polonik

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. A. Ogurtsov & O. A. Rakitin

  3. Nanotechnology Education and Research Center, South Ural State University, 76 prosp. V. I. Lenina, 454080, Chelyabinsk, Russian Federation

    O. A. Rakitin

Authors
  1. S. N. Fedorov
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  2. A. S. Kuzmich
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  3. Yu. E. Sabutskii
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  4. A. G. Guzii
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  5. R. S. Popov
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  6. V. A. Ogurtsov
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  7. O. A. Rakitin
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  8. S. G. Polonik
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Corresponding authors

Correspondence to S. N. Fedorov or O. A. Rakitin.

Additional information

The authors are grateful to Professor Z. Dong (Hormel Institute, Austin, Minnesota, USA), who kindly provided the JB6 cells used in this work. The authors are grateful to the co-workers of the G. B. Elyakov Pacific Institute of Bioorganic Chemistry Ph. D. (Chem.) V. A. Denisenko and Ph. D. (Phys.-Math.) V. P. Glazunov for recording the NMR and IR spectra.

The study was carried out on the equipment of the Collective Facilities Center “The Far Eastern Center for Structural Molecular Research (NMR/MS) PIBOC FEB RAS”.

This work was financially supported by the Program for the Development of Scientific Schools of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences (Project NSh No. 31).

This work does not involve human participants and animal subjects.

The authors declare no competing interest.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 573–579, March, 2021.

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Fedorov, S.N., Kuzmich, A.S., Sabutskii, Y.E. et al. Synthesis and studies of acetylthioglycoside conjugates of 4-chloro-1,2-dithiole-3-thione as potential antitumor agents. Russ Chem Bull 70, 573–579 (2021). https://doi.org/10.1007/s11172-021-3127-1

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  • DOI: https://doi.org/10.1007/s11172-021-3127-1

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