Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents
Uticaj strukture na antiproliferativnu i antibakterijsku aktivnost 3-supstituisanih-5,5-difenilhidantoina
Authors
Trišović, NemanjaBožić, Bojan
Obradović, Ana
Stefanović, Olgica
Marković, Snežana
Čomić, Ljiljana
Božić, Biljana
Ušćumlić, Gordana
Article (Published version)
Metadata
Show full item recordAbstract
A series of twelve 3-substituted-5,5-diphenylhydantoins was synthesized, including some whose anticonvulsant activities have already been reported in the literature. Their antiproliferative activities against HCT-116 human colon carcinoma cells were evaluated to determine structure-activity relationships. Almost all of the compounds exhibited statistically significant antiproliferative effects at a concentration of 100 μM, while the derivative bearing a benzyl group was active even at lower concentrations. Moreover, their in vitro antibacterial activities against Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and clinical isolates of Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis and Staphylococcus aureus were evaluated. Only the 3-isopropyl and 3-benzyl derivatives showed weak antibacterial activities against the Gram-positive bacterium E. faecalis and the Gram-negative bacteria E. coli ATCC 25922 and E. coli.
Sintetisana je serija od dvanaest 3-supstituisanih-5,5-difenilhidantoina, koja obuhvata neke od derivata čije su antikonvulzivne aktivnosti poznate u literaturi. Određena je njihova antiproliferativna aktivnost prema ćelijskoj liniji humanog karcinoma kolona, kako bi se utvrdio uticaj strukture na aktivnost. Skoro sva jedinjenja ispoljavaju antiproliferativan efekat u koncentraciji od 100 μM, dok je derivat sa benzil grupom aktivan i u nižim koncentracijama. Dodatno je određena i antibakterijska aktivnost proučavanih jedinjenja prema Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 i kliničkim izolatima Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis i Staphylococcus aureus. 3-Izopropil i 3-benzil derivati pokazuju slabu aktivnost prema gram-pozitivnoj bakteriji E. faecalis i gram-negativnim bakterijama E. coli ATCC 25922 i E. coli.
Keywords:
phenytoin derivatives / antiproliferative activity / antimicrobial activity / structure-activity relationshipSource:
Journal of the Serbian Chemical Society, 2011, 76, 12, 1597-1606Publisher:
- Serbian Chemical Society, Belgrade
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Trišović, Nemanja AU - Božić, Bojan AU - Obradović, Ana AU - Stefanović, Olgica AU - Marković, Snežana AU - Čomić, Ljiljana AU - Božić, Biljana AU - Ušćumlić, Gordana PY - 2011 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1797 AB - A series of twelve 3-substituted-5,5-diphenylhydantoins was synthesized, including some whose anticonvulsant activities have already been reported in the literature. Their antiproliferative activities against HCT-116 human colon carcinoma cells were evaluated to determine structure-activity relationships. Almost all of the compounds exhibited statistically significant antiproliferative effects at a concentration of 100 μM, while the derivative bearing a benzyl group was active even at lower concentrations. Moreover, their in vitro antibacterial activities against Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and clinical isolates of Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis and Staphylococcus aureus were evaluated. Only the 3-isopropyl and 3-benzyl derivatives showed weak antibacterial activities against the Gram-positive bacterium E. faecalis and the Gram-negative bacteria E. coli ATCC 25922 and E. coli. AB - Sintetisana je serija od dvanaest 3-supstituisanih-5,5-difenilhidantoina, koja obuhvata neke od derivata čije su antikonvulzivne aktivnosti poznate u literaturi. Određena je njihova antiproliferativna aktivnost prema ćelijskoj liniji humanog karcinoma kolona, kako bi se utvrdio uticaj strukture na aktivnost. Skoro sva jedinjenja ispoljavaju antiproliferativan efekat u koncentraciji od 100 μM, dok je derivat sa benzil grupom aktivan i u nižim koncentracijama. Dodatno je određena i antibakterijska aktivnost proučavanih jedinjenja prema Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 i kliničkim izolatima Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis i Staphylococcus aureus. 3-Izopropil i 3-benzil derivati pokazuju slabu aktivnost prema gram-pozitivnoj bakteriji E. faecalis i gram-negativnim bakterijama E. coli ATCC 25922 i E. coli. PB - Serbian Chemical Society, Belgrade T2 - Journal of the Serbian Chemical Society T1 - Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents T1 - Uticaj strukture na antiproliferativnu i antibakterijsku aktivnost 3-supstituisanih-5,5-difenilhidantoina EP - 1606 IS - 12 SP - 1597 VL - 76 UR - https://hdl.handle.net/21.15107/rcub_technorep_1797 ER -
@article{ author = "Trišović, Nemanja and Božić, Bojan and Obradović, Ana and Stefanović, Olgica and Marković, Snežana and Čomić, Ljiljana and Božić, Biljana and Ušćumlić, Gordana", year = "2011", abstract = "A series of twelve 3-substituted-5,5-diphenylhydantoins was synthesized, including some whose anticonvulsant activities have already been reported in the literature. Their antiproliferative activities against HCT-116 human colon carcinoma cells were evaluated to determine structure-activity relationships. Almost all of the compounds exhibited statistically significant antiproliferative effects at a concentration of 100 μM, while the derivative bearing a benzyl group was active even at lower concentrations. Moreover, their in vitro antibacterial activities against Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 and clinical isolates of Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis and Staphylococcus aureus were evaluated. Only the 3-isopropyl and 3-benzyl derivatives showed weak antibacterial activities against the Gram-positive bacterium E. faecalis and the Gram-negative bacteria E. coli ATCC 25922 and E. coli., Sintetisana je serija od dvanaest 3-supstituisanih-5,5-difenilhidantoina, koja obuhvata neke od derivata čije su antikonvulzivne aktivnosti poznate u literaturi. Određena je njihova antiproliferativna aktivnost prema ćelijskoj liniji humanog karcinoma kolona, kako bi se utvrdio uticaj strukture na aktivnost. Skoro sva jedinjenja ispoljavaju antiproliferativan efekat u koncentraciji od 100 μM, dok je derivat sa benzil grupom aktivan i u nižim koncentracijama. Dodatno je određena i antibakterijska aktivnost proučavanih jedinjenja prema Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 25923 i kliničkim izolatima Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Enterococcus faecalis i Staphylococcus aureus. 3-Izopropil i 3-benzil derivati pokazuju slabu aktivnost prema gram-pozitivnoj bakteriji E. faecalis i gram-negativnim bakterijama E. coli ATCC 25922 i E. coli.", publisher = "Serbian Chemical Society, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents, Uticaj strukture na antiproliferativnu i antibakterijsku aktivnost 3-supstituisanih-5,5-difenilhidantoina", pages = "1606-1597", number = "12", volume = "76", url = "https://hdl.handle.net/21.15107/rcub_technorep_1797" }
Trišović, N., Božić, B., Obradović, A., Stefanović, O., Marković, S., Čomić, L., Božić, B.,& Ušćumlić, G.. (2011). Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents. in Journal of the Serbian Chemical Society Serbian Chemical Society, Belgrade., 76(12), 1597-1606. https://hdl.handle.net/21.15107/rcub_technorep_1797
Trišović N, Božić B, Obradović A, Stefanović O, Marković S, Čomić L, Božić B, Ušćumlić G. Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents. in Journal of the Serbian Chemical Society. 2011;76(12):1597-1606. https://hdl.handle.net/21.15107/rcub_technorep_1797 .
Trišović, Nemanja, Božić, Bojan, Obradović, Ana, Stefanović, Olgica, Marković, Snežana, Čomić, Ljiljana, Božić, Biljana, Ušćumlić, Gordana, "Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents" in Journal of the Serbian Chemical Society, 76, no. 12 (2011):1597-1606, https://hdl.handle.net/21.15107/rcub_technorep_1797 .