Novel steroid sulfatase inhibitors based on N ‐thiophosphorylated 3‐(4‐aminophenyl)‐coumarin‐7‐O‐sulfamates - Publikacja - MOST Wiedzy

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Novel steroid sulfatase inhibitors based on N ‐thiophosphorylated 3‐(4‐aminophenyl)‐coumarin‐7‐O‐sulfamates

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In the present work, we described convenient methods for the synthesis ofN-thiophosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates as steroid sulfatase(STS) inhibitors. To design the structures of the potential STS inhibitors, molecularmodeling techniques were used. A computational docking method was used to deter-mine the binding modes of the synthesized inhibitors as well as to identify potentialinteractions between specified functional groups on the inhibitors and the amino acidresidues present in the active site of the enzyme. The inhibitory activities of the syn-thesized compounds were tested in an enzymatic assay with STS isolated from ahuman placenta. Within the set of newly synthesized compounds,9edemonstratedthe highest inhibitory activity in the enzymatic assay with an IC50value of 0.201μM(the IC50value of667-COUMATEin the same test was 0.062μM). Furthermore, wetried to verify if the obtained STS inhibitors are able to pass through the cellular mem-brane effectively in cell line experiments. In the course of our study, we determinedthe STS activity in the MCF-7 cell line after incubation in the presence of the inhibitors(at 100 nM concentration). For this evaluation, we included newly synthesized com-pounds9a-gand theirN-phosphorylated analogs6a-h, whose synthesis has been pre-viously described. We found that the lowest STS activities were measured in thepresence ofN-phosphorylated derivatives6e(0.1% of STS activity) and6f(0.2% ofSTS activity). The measured STS activity in the presence of667-COUMATE(used as areference) was 0.1%. Moreover, at concentrations up to 1μM, the most active com-pounds (6e,6f,9b,and9e) did not exert any toxic effects on zebrafish embryos.

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Copyright (2019 Wiley Periodicals, Inc.)

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Kategoria:
Publikacja w czasopiśmie
Typ:
artykuły w czasopismach
Opublikowano w:
DRUG DEVELOPMENT RESEARCH nr 80, strony 857 - 866,
ISSN: 0272-4391
Język:
angielski
Rok wydania:
2019
Opis bibliograficzny:
Daśko M., Demkowicz S., Biernacki K., Harrous A., Rachoń J., Kozak W., Martyna A., Masłyk M., Kubiński K., Boguszewska‐czubara A.: Novel steroid sulfatase inhibitors based on N ‐thiophosphorylated 3‐(4‐aminophenyl)‐coumarin‐7‐O‐sulfamates// DRUG DEVELOPMENT RESEARCH -Vol. 80,iss. 6 (2019), s.857-866
DOI:
Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1002/ddr.21569
Bibliografia: test
  1. Daśko, M., Masłyk, M., Kubiński, K., Aszyk, J., Rachon, J., & Demkowicz, S. (2016). Synthesis and steroid sulfatase inhibitory activities of N-phosphorylated 3-(4-aminophenyl)-coumarin-7-O-sulfamates, Med. Chem. Commun., 7, 1146-1150. otwiera się w nowej karcie
  2. Daśko, M., Przybyłowska, M., Rachon, J., Masłyk, M., Kubiński, K., Misiak, M., Składanowski, A., & otwiera się w nowej karcie
  3. Demkowicz, S. (2017). Synthesis and biological evaluation of fluorinated N-benzoyl and N-phenylacetoyl derivatives of 3-(4-aminophenyl)-coumarin-7-O-sulfamate as steroid sulfatase inhibitors, Eur. J. Med. Chem., 128, 79-87.
  4. Demkowicz, S., Daśko, M., Kozak, W., Krawczyk, K., Witt, D., Masłyk, M., Kubiński, K., & Rachon, J. (2016). Synthesis and biological evaluation of fluorinated 3-phenylcoumarin-7-O-sulfamate derivatives as steroid sulfatase inhibitors, Chem. Biol. Drug. Des., 87, 233-238. otwiera się w nowej karcie
  5. Ferlay, J., Shin, H.R., Bray, F., Forman, D., Mathers, C., & Parkin, D.M. (2010). Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008, Int. J. Cancer, 127, 2893-2917. otwiera się w nowej karcie
  6. Ganeshapillai, D., Woo, L.W.L, Thomas, M.P., Purohit, A., & Potter, B.V.L. (2018). C-3-and C-4-Substituted Bicyclic Coumarin Sulfamates as Potent Steroid Sulfatase Inhibitors, ACS Omega, 3, 10748−10772. otwiera się w nowej karcie
  7. Hernandez-Guzman, F. G., Higashiyama, T., Osawa, Y., & Ghosh, D. (2001). Purification, characterization and crystallization of human placental estrone/dehydroepiandrosterone sulfatase, a membrane-bound enzyme of the endoplasmic reticulum. J. Steroid Biochem. Mol. Biol. 78, 441-450. otwiera się w nowej karcie
  8. Jacobson, R.M., & Nguyen, L.T. (1999). Phosphoryl hydrazine insecticides, US Pat., 6147062A.
  9. Kozak, W., Daśko, M., Masłyk, M., Gielniewski, B., Rachon, J., & Demkowicz, S. (2015). Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors, J. Asian Nat. Prod. Res., 17, 1091-1096. otwiera się w nowej karcie
  10. Kozak, W., Daśko, M., Masłyk, M., Pieczykolan, J.S., Gielniewski, B., Rachon, J., & Demkowicz, S. (2014). Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: synthesis and biological activity, RSC Adv., 4, 44350-44358. otwiera się w nowej karcie
  11. Malini, B., Purohit, A., Ganeshapillai, D., Woo, L.W.L., Potter, B.V.L., & Reed, M.J. (2000). Inhibition of steroid sulphatase activity by tricyclic coumarin sulphamates, J. Steroid. Biochem. Mol. Biol., 75, 253-258. otwiera się w nowej karcie
  12. Potter, B.V.L. (2018). Steroid sulphatase inhibition via aryl sulphamates: clinical progress, mechanism and future prospects, J. Mol. Endocrinol., 61, 233-252. otwiera się w nowej karcie
  13. Purohit, A., Reed, M.J., Morris, N.C., Williams, G.J., & Potter, B.V.L. (1996). Regulation and inhibition of steroid sulfatase activity in breast cancer, Ann. N.Y. Acad. Sci., 784, 40-49. otwiera się w nowej karcie
  14. Shah, R., Singh, J., Singh, D., Singh Jaggi, A., & Singh, N. (2016). Sulfatase inhibitors for recidivist breast cancers treatment: A chemical review. Eur. J. Med. Chem., 114, 170-190. otwiera się w nowej karcie
  15. Thomas, M.P., & Potter, B.V.L. (2015). Discovery and Development of the Aryl O-Sulfamate Pharmacophore for Oncology and Women's Health, J. Med. Chem., 58, 7634-7658. otwiera się w nowej karcie
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  17. Trott, O., & Olson, A. J. (2010). AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading., J. Comput. Chem., 31, 455-461. otwiera się w nowej karcie
  18. Vaccaro, A.M., Salvioli, R., Muscillo, M., & Renola, L. (1987). Purification and properties of arylsulfatase C from human placenta, Enzyme, 37, 115-126. otwiera się w nowej karcie
  19. Woo, L.W.L., Howarth, N.M., Purohit, A., Hatem, A.M., Reed, M.J., & Potter, B.V.L. (1998). Steroidal and nonsteroidal sulfamates as potent inhibitors of steroid sulfatase, 41, 1068-1083. otwiera się w nowej karcie
  20. Woo, L.W.L., Jackson, T., Putey, A., Cozier, G., Leonard, P., Acharya, K.R., Chander, S.K., Purohit, A., Reed, M.J., & Potter, B.V.L. (2010). Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template, J. Med. Chem., 53, 2155-2170. otwiera się w nowej karcie
Weryfikacja:
Politechnika Gdańska

wyświetlono 151 razy

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