Efficient synthesis and antifungal investigation of nucleosides’ quaternary ammonium salt derivatives - Publication - Bridge of Knowledge

Your account

login

Search

Efficient synthesis and antifungal investigation of nucleosides’ quaternary ammonium salt derivatives

Abstract

Quaternary ammonium salts are a group of compounds with diverse biological properties, the most important of which are their antiviral, antibacterial, and antifungal activities. The quaternization reactions of 5'-O-tosyl derivatives of uridine and thymidine with triethylamine, trimethylamine, 4-(N ,N -dimethylamino)pyridine, 2-methylpyridine, and pyridine are described in this article. Two of the synthesized compounds are exceptional because they are first of this type that demonstrate concentration-dependent antifungal in vitro activity against two species of the genus Candida in minimal YNB-SG medium. The experimental results have been extended by adding full atom molecular dynamics simulations and substrates and products energies evaluation.

Citations

  • 1

    CrossRef

  • 0

    Web of Science

  • 1

    Scopus

Authors (6)

Cite as

Full text

download paper
downloaded 46 times
Publication version
Accepted or Published Version
License
Creative Commons: CC-BY open in new tab

Keywords

Details

Category:
Articles
Type:
artykuł w czasopiśmie wyróżnionym w JCR
Published in:
TURKISH JOURNAL OF CHEMISTRY no. 43, pages 157 - 171,
ISSN: 1300-0527
Language:
English
Publication year:
2019
Bibliographic description:
Dmochowska B., Pellowska-Januszek L., Samaszko J., Ślusarz R., Wakieć R., Madaj J.: Efficient synthesis and antifungal investigation of nucleosides’ quaternary ammonium salt derivatives// TURKISH JOURNAL OF CHEMISTRY. -Vol. 43, (2019), s.157-171
DOI:
Digital Object Identifier (open in new tab) 10.3906/kim-1808-34
Bibliography: test
  1. Li, N.; Smith, T. J.; Zong, M. H. Biotechnol. Adv. 2010, 28, 348-366. open in new tab
  2. Ralevic, V.; Burnstock G. Pharmacol. Rev. 1998, 50, 413-492.
  3. Jacobson, K. A.; Jarvis, M. F.; Williams, M. J. Med. Chem. 2002, 45, 4057-4093. open in new tab
  4. Young, J. F.; Therkildsen, M.; Ekstrand, B.; Che, B. N.; Larsen, M. K.; Oksbjerg, N.; Stagsted, J. Meat. Sci. 2013, 95, 904-911. open in new tab
  5. Uauy, R.; Quan, R.; Gil, A. J. Nutr. 1994, 124, 1436S-1441S. open in new tab
  6. Micheli, V.; Camici, M.; Tozzi, M. G.; Ipata, P. L.; Sestini, S.; Bertelli, M.; Pompucci, G. Curr. Top. Med. Chem. 2011, 11, 923-947. open in new tab
  7. Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875-1916. open in new tab
  8. Robins, M. J. In Nucleoside Analogues: Chemistry, Biology, and Medical Applications; Walker, R. T.; DeClercq, E.; Eckstein, F., Eds. Plenum Press: New York, NY, USA, 1979, pp. 165-192. open in new tab
  9. Townsend, L. B. In Nucleoside Analogues: Chemistry, Biology, and Medical Applications; Walker, R. T.; DeClercq, E.; Eckstein, F., Eds. Plenum Press: New York, NY, USA, 1979, pp. 193-223. open in new tab
  10. Lee, S. E.; Sidorov, A.; Gourlain, T.; Mignet, N.; Thorpe, S. J.; Brazier, J. A.; Dickman, M. J.; Hornby, D. P.; Grasby, J. A.; Williams, D. M. Nucleic Acids Res. 2001, 29, 1565-1573. open in new tab
  11. Sakthivel, K.; Barbas, C. F. Angew. Chem. Int. Ed. Engl. 1998, 37, 2872-2875. open in new tab
  12. Ruth, J. L. In Oligonucleotides and Analogues; open in new tab
  13. Eckstein, F., Ed. OUP: New York, NY, USA, 1991, pp. 255-281. open in new tab
  14. Anderson, J. P.; Angerer, B.; Loeb, L. A. Biotechniques 2005, 38, 257-264. open in new tab
  15. Abdoli, M.; Mirjafary, Z.; Saeidian, H.; Kakanejadifard, A. RSC Adv. 2015, 5, 44371-44389. open in new tab
  16. Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99-134. open in new tab
  17. Eaton, B. E.; Pieken, W. A. Annu. Rev. Biochem. 1995, 64, 837-863. open in new tab
  18. Pankiewicz, K. W. Carbohydr. Res. 2000, 327, 87-105. open in new tab
  19. Sproat, B. S.; Lamond, A. I. In Oligonucleotides and Analogues. Eckstein, F. , Ed. OUP: New York, NY, USA, 1991, pp. 49-86. open in new tab
  20. Beigelman, L.; Haeberli, P.; Sweedler, D.; Karpeisky, A. Tetrahedron 2000, 56, 1047-1056. open in new tab
  21. Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902-7908. open in new tab
  22. Rao, A. V. R.; Gurjar, M. K.; Lalitha, S. V. S. J. Chem. Soc. Chem. Commun. 1994, 1255-1256. open in new tab
  23. Cano-Soldado, P.; Pastor-Anglada, M. Med. Res. Rev. 2012, 32, 428-457. open in new tab
  24. Minuesa, G.; Huber-Ruano, I.; Pastor-Anglada, M.; Koepsell, H.; Clotet, B.; Martinez-Picado, J. Pharmacol. Ther. 2011, 132, 268-279. open in new tab
  25. Pathak, T. Chem. Rev. 2002, 102, 1623-1668. open in new tab
  26. Pastor-Anglada, M.; Felipe, A.; Casado, F. J. Trends Pharmacol. Sci. 1998, 19, 424-430. open in new tab
  27. Connolly, G. P.; Duley, J. A. Trends Pharmacol. Sci. 1999, 20, 218-225. open in new tab
  28. Koyama, G.; Maeda, K.; Umezawa, H. Tetrahedron Lett. 1966, 6, 597-602. open in new tab
  29. Krugh, T. R. J. Am. Chem. Soc. 1973, 95, 4761-4762. open in new tab
  30. Horowitz, J. P.; Tomson, A. J.; Urbański, J. A.; Chua, J. J. Org. Chem. 1962, 27, 3045-3048. open in new tab
  31. Lin, T. S.; Prusoff, W. H. J. Med. Chem. 1978, 21, 109-112. open in new tab
  32. Horowitz, J. P.; Chua, J.; Noel, M. J. Org. Chem. 1964, 29, 2076-2078. open in new tab
  33. Miller, N.; Fox, J. J. J. Org. Chem. 1964, 29, 1772-1776. open in new tab
  34. Kuca, K.; Kivala, M.; Dohnal, V. J. Appl. Biomed. 2004, 2, 195-198.
  35. Quagliotto, P.; Viscardi, G.; Barolo, C.; DÁngelo, D.; Barni, E.; Compari, C.; Duce, E.; Fisicaro, E. J. Org. Chem. 2005, 70, 9857-9866. open in new tab
  36. Michelson, A. M.; Todd, A. R. J. Chem. Soc. 1955, 816-823. open in new tab
  37. Skorupa, E.; Dmochowska, B.; Pellowska-Januszek, L.; Wojnowski, W.; Chojnacki, J.; Wi textquotesinglesniewski, A. Carobohydr. Res. 2004, 339, 2355-2362.
  38. Pellowska-Januszek, L.; Dmochowska, B.; Skorupa, E.; Chojnacki, J.; Wojnowski, W.; Wiśniewski, A. Carbohydr. Res. 2004, 339, 1537-1544. open in new tab
  39. Fromageot, H. P. M.; Griffin, B. E.; Reese, C. B.; Sulston, J. E. Tetrahedron 1967, 23, 2315-2331. open in new tab
  40. Shuman, A.; Robins, R. K.; Robins, M. J. J. Am. Chem. Soc. 1969, 91, 3391-3392. open in new tab
  41. Case, D. A.; Darden, T. A.; Cheatham, T. E. 3rd;
  42. Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Walker, R. C.; Zhang, W.; Merz, K. M. et al. AMBER 12; University of California: San Francisco, CA, USA, 2012.
  43. Duan, Y.; Wu, C.; Chowdhury, S.; Lee, M. C.; Xiong, G.; Zhang, W.; Yang, R.; Cieplak, P.; Luo, R.; Lee, T. et al J. Comput. Chem. 2003, 24, 1999-2012. open in new tab
  44. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. J. Comput. Chem. 2004, 25, 1157-1174. open in new tab
  45. Cieplak, P.; Cornell, W. D.; Bayly, C.; Kollman, P. A. J. Comput. Chem. 1995, 16, 1357-1377. open in new tab
  46. Onufriev, A.; Bashford, D.; Case, D. A. J. Phys. Chem. B 2000, 104, 3712-3720. open in new tab
  47. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327-341. open in new tab
  48. Berendsen, H. J. C.; Postma, J. P. M.; van Gunsteren, W. F.; DiNola, A.; Haak, J. R. J. Chem. Phys. 1984, 81, 3684-3690. open in new tab
  49. Ewald, P. P. Ann. Phys. 1921, 369, 253-287. open in new tab
  50. Darden, T.; Perera, L.; Li, L.; Pedersen, L. Structure 1999, 7, R55-R60. open in new tab
  51. Salomon-Ferrer, R.; Götz, A. W.; Poole, D.; Le Grand, S.; Walker, R. C. J. Chem. Theory Comput. 2013, 9, 3878-3888. open in new tab
  52. Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T., Zurek, E.; Hutchison, G. R. J. Cheminform. 2012, 4, 17. open in new tab
  53. Halgren, T. A. J. Comput. Chem. 1999, 20, 720-729. open in new tab
  54. Stewart, J. J. P. J. Mol. Model. 2007, 13, 1173-1213. open in new tab
  55. Stewart, J. J. P. MOPAC2016; Stewart Computational Chemistry: Colorado Springs, CO, USA, 2016. open in new tab
  56. Newth, F. H.; Phillips, G. O. J. Chem. Soc. 1953, 2904-2909. open in new tab
Verified by:
Gdańsk University of Technology

seen 147 times

Recommended for you

New class of quaternary ammonium salts, derivatives of methyl D-glucopyranosides.

  • L. Pellowska-Januszek,
  • B. Dmochowska,
  • E. Skorupa
  • + 3 authors
2004

The Substantial Improvement of Amphotericin B Selective Toxicity Upon Modification of Mycosamine with Bulky Substituents

2020

New Simple and Robust Method for Determination of Polarity of Deep Eutectic Solvents (DESs) by Means of Contact Angle Measurement

2022

Novel Nystatin A1 derivatives exhibiting low host cell toxicity and antifungal activity in an in vitro model of oral candidosis

2014
Meta Tags