Synthesis and biological evaluation of N-acylated tyramine sulfamates containing C-F bonds as steroid sulfatase inhibitors

Mateusz Daśko; Janusz Rachoń; Maciej Masłyk; Konrad Kubiński; Sebastian Demkowicz

doi:10.1111/cbdd.12931

Synthesis and biological evaluation of N-acylated tyramine sulfamates containing C-F bonds as steroid sulfatase inhibitors

Abstract

Steroid sulfatase (STS) is responsible for the hydrolysis of biologically inactive sulfated steroids into their active un-sulfated forms and promotes the growth of various hormone-dependent cancers (e.g., breast cancer). Therefore, the STS enzyme is a promising therapeutic target for the treatment of steroid-sensitive cancers. Herein, we report the synthesis and biological evaluation of sulfamate analogs as potential STS inhibitors based on N-acylated tyramines that contain C–F bonds. The inhibitory effects of the analogs were tested using STS isolated from human placenta. Of the analogs tested, 4-(2-perfluoroundecanoylaminoethyl)-phenyl sulfamate, 5r, demonstrated the greatest inhibitory effect, with an IC50 value of 2.18 μm (IC50 value of 2.13 μm for coumarin-7-O-sulfamate was used as a reference). These findings were supported by the results our computational analyses performed using molecular docking techniques.

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Authors (5)

Mateusz Daśko dr inż.
Janusz Rachoń prof. dr hab. inż.
Maciej Masłyk
- Katolicki Uniwersytet Lubelski
Konrad Kubiński
- Katolicki Uniwersytet Lubelski
Sebastian Demkowicz dr hab. inż.

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Category:: Articles
Type:: artykuł w czasopiśmie wyróżnionym w JCR
Published in:: Chemical Biology & Drug Design no. 90, edition 1, pages 156 - 161,
ISSN: 1747-0277
Language:: English
Publication year:: 2017
Bibliographic description:: Daśko M., Rachoń J., Masłyk M., Kubiński K., Demkowicz S.: Synthesis and biological evaluation of N-acylated tyramine sulfamates containing C-F bonds as steroid sulfatase inhibitors// Chemical Biology & Drug Design. -Vol. 90, iss. 1 (2017), s.156-161
DOI:: Digital Object Identifier (open in new tab) 10.1111/cbdd.12931
Verified by:: Gdańsk University of Technology