Journal Title
Title of Journal: Struct Chem
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Abbravation: Structural Chemistry
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Authors: Olivera R Klisurić Mihály Szécsi Evgenija A Djurendić Szabó Nikoletta Bianka Edina Herman Suzana S Jovanović Šanta Sanja V Dojčinović Vujašković Andrea R Nikolić Ksenija J Pavlović Jovana J Ajduković Aleksandar M Oklješa Edward T Petri Vesna V Kojić Marija N Sakač Katarina M Penov Gaši
Publish Date: 2015/09/19
Volume: 27, Issue: 3, Pages: 947-960
Abstract
New estrane salicyloyloxy or Dhomo derivatives were synthesized under microwave MW or conventional heating from estrane precursors and methyl salicylate The MW technique provides advantages regarding product yield and reaction time and represents a more environmentally friendly approach than conventional heating Considering the biomedical potential of estrane compounds we evaluated the antioxidant activity and cytotoxicity of synthesized estrane derivatives in a series of in vitro tests as well as their 3βhydroxysteroid dehydrogenase/Δ5 → Δ4 isomerase 3βHSD and 17βhydroxysteroid dehydrogenase types 1 2 and 3 17βHSD1 17βHSD2 and 17βHSD3 inhibition potentials In DPPH tests 3methoxyestra13510trien17βyl salicylate displayed antioxidant potential while all compounds exhibited OH radical neutralization activity 3Oxoestr4en17βyl salicylate showed strong cytotoxicity against MDAMB231 breast cancer cells while 17oxoestra13510trien3yl salicylate estra13510triene317βdiyl 3benzoate 17salicylate and 3benzyloxy17salicyloyloxy1617secoestra13510triene16nitrile showed the strongest inhibition of PC3 prostate cancer cell growth 3Hydroxyestra13510trien17βyl salicylate was the best inhibitor of 17βHSD2 suggesting potential use in treating pathological conditions associated with estrogen depletion For 3methoxyestra13510trien17βyl salicylate and 3oxoestr4en17βyl salicylate Xray crystal structure analysis and molecular energy optimization were performed to define their conformations and energy minima Very good overlap in the region of the steroidal nucleus was observed for the molecular structures of each analyzed molecule in the crystalline state and after energy optimization while conformer analysis indicates conformational flexibility in the form of rotation around the C17···O2 bond Structural geometry analysis for these compounds shows that the region of ring A in steroids and especially the C3 atom functional group is important structural features concerning antiproliferative activity against MDAMB231 cellsAuthors would like to thank the HungarySerbia IPA Crossborder Cooperation Programme Project No HUSRB/1002/214/133 RECODAC Provincial Secretariat for Science and Technological Development of Vojvodina Grant No 114451946/201503 and Ministry of Education Science and Technological Development of the Republic of Serbia for financial support Grant No 172021 The work of N Szabó was supported by a PhD Fellowship of the Talentum Fund of Richter Gedeon Plc
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