New potent STS inhibitors based on fluorinated 4-(1-phenyl-1H-[1,2,3]triazol-4-yl)-phenyl sulfamates - Publication - Bridge of Knowledge

Search

New potent STS inhibitors based on fluorinated 4-(1-phenyl-1H-[1,2,3]triazol-4-yl)-phenyl sulfamates

Abstract

A series of fluorinated analogs based on the frameworks of 4-(1- phenyl-1H-[1,2,3]triazol-4-yl)-phenyl sulfamates have been synthesized as steroid sulfatase (STS) inhibitors. The design of chemical structures of new potential STS inhibitors was supported by molecular docking techniques to identify potential interactions between inhibitors and amino acid residues located in the STS active site. The STS inhibitory potency was evaluated on STS isolated from human placenta. We found that compounds substituted with fluorine atom at the meta position demonstrated the highest inhibitory effects in enzymatic STS assay. The most active analog 12e – inhibited STS enzyme with the IC50 value of 36 nM.

Citations

  • 5

    CrossRef

  • 5

    Web of Science

  • 5

    Scopus

Cite as

Full text

download paper
downloaded 20 times
Publication version
Accepted or Published Version
License
Copyright (2019 Informa UK Limited, trading as Taylor & Francis Group)

Keywords

Details

Category:
Articles
Type:
artykuły w czasopismach
Published in:
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH no. 22, pages 1037 - 1044,
ISSN: 1028-6020
Language:
English
Publication year:
2019
Bibliographic description:
Daśko M., Demkowicz S., Rachoń J., Biernacki K., Aszyk J., Kozak W., Masłyk M., Kubiński K.: New potent STS inhibitors based on fluorinated 4-(1-phenyl-1H-[1,2,3]triazol-4-yl)-phenyl sulfamates// JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH -Vol. 22,iss. 11 (2019), s.1037-1044
DOI:
Digital Object Identifier (open in new tab) 10.1080/10286020.2019.1680642
Bibliography: test
  1. R. Shah, J. Singh, D. Singh, A. Singh Jaggi, and N. Singh, Eur. J. Med. Chem. 114, 170 (2016). open in new tab
  2. S. Chumsri, T. Howes, T. Bao, G. Sabnis, and A. Brodie, J. Steroid Biochem. Mol. Biol. 125, 13 (2011). open in new tab
  3. J.Z. Jin, and S.-X. Lin, Biochem. Biophys. Res. Commun. 259, 489 (1999). open in new tab
  4. P.A. Foster, M.J. Reed, and A. Purohit, Anti-Cancer Agents Med. Chem. 8, 732 (2008). open in new tab
  5. M.J. Reed, A. Purohit, L.W.L. Woo, S.P. Newman, and B.V.L. Potter, Endocr. Rev. 26, 171 (2005). open in new tab
  6. A. Purohit, and P.A. Foster, J. Endocrinol. 212, 99 (2012). open in new tab
  7. A. Purohit, M.J. Reed, N.C. Morris, G.J. Williams, and B.V.L. Potter, Ann. N.Y. Acad. Sci. 784, 40 (1996). open in new tab
  8. B.V.L. Potter, J. Mol. Endocrinol. 61, 233 (2018). open in new tab
  9. M.P. Thomas, and B.V.L. Potter, J. Med. Chem. 58, 7634 (2015). open in new tab
  10. W. Kozak, M. Daśko, M. Masłyk, J.S. Pieczykolan, B. Gielniewski, J. Rachon, and S. Demkowicz, RSC Adv. 4, 44350 (2014). open in new tab
  11. W. Kozak, M. Daśko, A. Wołos, M. Masłyk, K. Kubiński, A. Składanowski, M. Misiak, J. Rachon, and S. Demkowicz, RSC Adv. 5, 32594 (2015). open in new tab
  12. S. Demkowicz, W. Kozak, M. Daśko, M. Masłyk, K. Kubiński, and J. Rachon, Drug Dev. Res. 76, 94 (2015). open in new tab
  13. W. Kozak, M. Daśko, M. Masłyk, K. Kubiński, J. Rachon, and S. Demkowicz, Drug Dev. Res. 76, 450 (2015). open in new tab
  14. S. Demkowicz, W. Kozak, M. Daśko, M. Masłyk, B. Gielniewski, and J. Rachon, Eur. J. Med. Chem. 101, 358 (2015). open in new tab
  15. W. Kozak, M. Daśko, M. Masłyk, B. Gielniewski, J. Rachon, and S. Demkowicz, J. Asian Nat. Prod. Res. 17, 1092 (2015).
  16. M. Daśko, M. Masłyk, K. Kubiński, J. Aszyk, J. Rachon, and S. Demkowicz, Med. Chem. Commun. 7, 1146 (2016). open in new tab
  17. L.W.L. Woo, N.M. Howarth, A. Purohit, A.M. Hatem, M.J. Reed, and B.V.L. Potter, J. Med. Chem. 41, 1068 (1998). open in new tab
  18. B. Malini, A. Purohit, D. Ganeshapillai, L.W.L. Woo, B.V.L. Potter, and M.J. Reed, J. Steroid Biochem. Mol. Biol. 75, 253 (2000). open in new tab
  19. S. Demkowicz, M. Daśko, W. Kozak, K. Krawczyk, D. Witt, M. Masłyk, K. Kubiński, and J. Rachon, Chem. Biol. Drug Des. 87, 233 (2016). open in new tab
  20. M. Daśko, M. Przybyłowska, J. Rachon, M. Masłyk. K. Kubiński, M. Misiak, A. Składanowski, and S. Demkowicz, Eur. J. Med. Chem. 128, 79 (2017). open in new tab
  21. M. Daśko, J. Rachon, M. Masłyk, K. Kubiński, and S. Demkowicz, Chem. Biol. Drug Des. 90, 156 (2017). open in new tab
  22. S. Demkowicz, K. Filipiak, M. Maslyk, J. Ciepielski, S. de Pascual-Teresa, S. Martin-Santamaria, B. de Pascual-Teresa, and A. Ramos, RSC Adv. 3, 3697 (2013). open in new tab
  23. A.M. Vaccaro, R. Salvioli, M. Muscillo, and L. Renola, Enzyme 37, 115 (1987). open in new tab
  24. L.W.L. Woo, T. Jackson, A. Putey, G. Cozier, P. Leonard, K.R. Acharya, S.K. Chander, A. Purohit, M.J. Reed, and B.V.L. Potter, J. Med. Chem. 53, 2155 (2010). open in new tab
Sources of funding:
Verified by:
Gdańsk University of Technology

seen 84 times

Recommended for you

Meta Tags