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Amphiphilic derivatives of (3β,17β)-3-hydroxyandrost-5-ene-17-carboxylic acid

Z. Özdemir, U. Bildziukevich, D. Šaman, L. Havlíček, L. Rárová, L. Navrátilová, Z. Wimmer,

. 2017 ; 128 (-) : 58-67. [pub] 20171031

Jazyk angličtina Země Spojené státy americké

Typ dokumentu časopisecké články, práce podpořená grantem

Perzistentní odkaz   https://www.medvik.cz/link/bmc18033600

A series of amphiphilic derivatives of (3β,17β)-3-hydroxyandrost-5-ene-17-carboxylic acid (1) with the polyamine spermine and three other diamines, 1,2-diaminoethane, piperazine and cadaverine, were synthesized and their antimicrobial activity and cytotoxicity were investigated. Among the target compounds, several ones showed antimicrobial activity on Gram positive and Gram negative microorganisms. The most active compounds were 20 (Streptococcus mutans CCM 7409, 3.125 µM), 16 (Streptococcus mutans CCM 7409, 12.5 µM) and 10d (Escherichia coli CCM 3954, 12.5 µM). In addition, compounds 5d, 10d, 13 and 20 displayed cytotoxicity on CEM (12.1 ± 2.1 µM, 7.6 ± 1.0 µM, 19.0 ± 0.4 µM and 5.9 ± 0.7 µM, respectively). Two additional compounds displayed medium cytotoxicity on CEM, 5a (34.6 ± 5.2 µM) and 5c (37.7 ± 5.9 µM). The compound 13 and 20 displayed high toxicity also on normal fibroblasts.

Citace poskytuje Crossref.org

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$a A series of amphiphilic derivatives of (3β,17β)-3-hydroxyandrost-5-ene-17-carboxylic acid (1) with the polyamine spermine and three other diamines, 1,2-diaminoethane, piperazine and cadaverine, were synthesized and their antimicrobial activity and cytotoxicity were investigated. Among the target compounds, several ones showed antimicrobial activity on Gram positive and Gram negative microorganisms. The most active compounds were 20 (Streptococcus mutans CCM 7409, 3.125 µM), 16 (Streptococcus mutans CCM 7409, 12.5 µM) and 10d (Escherichia coli CCM 3954, 12.5 µM). In addition, compounds 5d, 10d, 13 and 20 displayed cytotoxicity on CEM (12.1 ± 2.1 µM, 7.6 ± 1.0 µM, 19.0 ± 0.4 µM and 5.9 ± 0.7 µM, respectively). Two additional compounds displayed medium cytotoxicity on CEM, 5a (34.6 ± 5.2 µM) and 5c (37.7 ± 5.9 µM). The compound 13 and 20 displayed high toxicity also on normal fibroblasts.
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$a Šaman, David $u Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo náměstí 2, 16610 Prague 6, Czech Republic.
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$a Rárová, Lucie $u Department of Chemical Biology and Genetics, Centre of the Region Haná for Biotechnological and Agricultural Research, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic.
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$a Navrátilová, Lucie $u Department of Microbiology, Faculty of Medicine and Dentistry, Palacký University, Hněvotínská 3, 77515 Olomouc, Czech Republic.
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$a Wimmer, Zdeněk $u University of Chemistry and Technology, Prague, Department of Chemistry of Natural Compounds, Technická 5, 16628 Prague 6, Czech Republic; Institute of Experimental Botany AS CR, v.v.i., Isotope Laboratory, Vídeňská 1083, 14220 Prague 4, Czech Republic. Electronic address: zdenek.wimmer@vscht.cz.
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