Kompleksi platine(II) i rutenijuma(II) sa diaminskim ligandima: sinteza, karakterizacija i citotoksičnost
COMPLEXES OF PLATINUM(II) ANDRUTHENIUM(II) WITH DIAMINELIGANDS: SYNTHESIS,CHARACTERIZATION ANDCITOTOXICITY
Апстракт
U ovom radu su opisani sinteza, karakterizacija i biološka aktivnost nove (S,S)-1,3-propandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline i njenih estara (metil,etil, n-propil, n-butil, izobutil, n-pentil i izopentil), koji su korišćeni za sintezukvadratno-planarnih Pt(II) jodido kompleksa, opšte formule [PtI2{(S,S)-R2pddchxp}].Takođe je opisana sinteza, karakterizacija i biološka aktivnost novihorganorutenijum(II) kompleksa sa estrima (S,S)-etandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline (metil, etil, n-propil, n-butil, izobutil i izopentil), opšteformule [(η6-p-cimen)RuCl{(S,S)-R2eddchxp}]PF6.Polazna kiselina je dobijena u reakciji (S)-2-amino-3-cikloheksilpropanskekiseline i 1,3-dibrompropana u vodenom rastvoru, dok je njena esterifikacija izvršenapomoću tionil-hlorida i odgovarajućeg alkohola. Jodido kompleksi platine(II) sudobijeni reakcijom kalijum-tetrahloridoplatinata(II) i odgovarajućih estara, uz dodatakkalijum-jodida, dok su odgovarajući rutenijum(II) kompleksi sin...tetisani u reakcijiizmeđu [(η6-p-cimen)RuCl2]2 i estara (S,S)-etandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline.Karakterizacija liganada je urađena klasičnim metodama: elementalnomanalizom, IC, (1H i 13C) NMR spektroskopijom i masenom spektrometrijom, dok sukompleksi pored navedenih metoda, okarakterisani i elektronskom apsorpcionomspektroskopijom, rendgenskom strukturnom analizom za kompleks [(η6-pcimen)RuCl{(S,S)-iBu2eddchxp}]PF6 i 195Pt NMR spektroskopijom za kompleks[PtI2{(S,S)-iBu2pddchxp}]. Na osnovu rezultata dobijenih karakterizacijom, utvrđeno jeda kompleksi platine(II) imaju kvadratno-planarnu strukturu, sa N,N’ bidentatnovezanim estarskim ligandima. Na osnovu rendgenske-strukturne analize kompleksa[(η6-p-cimen)RuCl{(S,S)-iBu2eddchxp}]PF6, potvrđena je pseudo-oktaedarskageometrija sintetisanih Ru(II) kompleksa, sa koordinacijom estarskog liganda preko...
In this work, the synthesis, characterization and biological activity of novel(S,S)-1,3-propanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid, its esters (methyl,ethyl, n-propyl, n-butyl, i-butyl, n-pentyl and i-pentyl) and corresponding square-planariodido Pt(II) complexes, of general formula [PtI2{(S,S)-R2pddchxp}], are presented. Inaddition, the synthesis, characterization and biological activity of novelorganorutenium(II) complexes with esters of (S,S)-ethanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid (methyl, ethyl, n-propyl, n-butyl, i-butyl and i-pentyl),general formula, of [(η6-p-cimen)RuCl{(S,S)-R2eddchxp}]PF6, were reported.Starting acid was obtained by reaction of (S)-2-amino-3-cyclohexyl-propanoicacid and 1,3-dibromopropane, in water solution, while esterification was performedwith thionyl chloride and corresponding alcohol. Iodido complexes of platinum(II) wereobtained by reaction of potassium tetrachloridoplatinate(II) and synthesized esters, withadding of potassium io...dide. Ruthenium(II) complexes were synthesized by reactionbetween [(η6-p-cymene)RuCl2]2 and different esters of (S,S)-ethanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid. Ligands were characterized by elemental analysis, IR,(1H and 13C) NMR spectroscopy and mass spectrometry, while the complexes, inaddition to these methods, were characterized and UV/Vis, single crystal X-raystructure diffraction analysis for [(η6-p-cymene)RuCl{(S,S)-iBu2eddchxp}]PF6 and 195PtNMR spectroscopy for [PtI2{(S,S)-iBu2pddchxp}]. Based on these results, it is foundthat complexes platinum(II) have square-planar geometry with coordination of ligandsvia nitrogen donor atoms of ester ligands. Single crystal X-ray structure diffractionanalysis of [(η6-p-cymene)RuCl{(S,S)-iBu2eddchxp}]PF6 showed the usual piano-stoolgeometry of complexes, with N,N’ coordination of ester ligands. The stability of thecomplexes of platinum and ruthenium in different solvents was investigated, as well asthe ability of these complexes to bind lysozyme...
Кључне речи:
Platinum(II) complexes / diamine ligands / organoruthenium(II) complexes / in vitro cytotoxicity / tumor cell lines / piano-stool geometry / kompleksi platine(II) / diaminski ligandi / organorutenijum(II) kompleksi / in vitro citotoksično dejstvo / tumorske ćelijske linije / pseudo-oktaedarska geometrijaИзвор:
Универзитет у Београду, 2014Издавач:
- Универзитет у Београду, Хемијски факултет
URI
http://eteze.bg.ac.rs/application/showtheses?thesesId=3703https://fedorabg.bg.ac.rs/fedora/get/o:12519/bdef:Content/download
http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=47667727
http://nardus.mpn.gov.rs/123456789/6385
https://cherry.chem.bg.ac.rs/handle/123456789/2703
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - THES AU - Savić, Aleksandar PY - 2014 UR - http://eteze.bg.ac.rs/application/showtheses?thesesId=3703 UR - https://fedorabg.bg.ac.rs/fedora/get/o:12519/bdef:Content/download UR - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=47667727 UR - http://nardus.mpn.gov.rs/123456789/6385 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2703 AB - U ovom radu su opisani sinteza, karakterizacija i biološka aktivnost nove (S,S)-1,3-propandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline i njenih estara (metil,etil, n-propil, n-butil, izobutil, n-pentil i izopentil), koji su korišćeni za sintezukvadratno-planarnih Pt(II) jodido kompleksa, opšte formule [PtI2{(S,S)-R2pddchxp}].Takođe je opisana sinteza, karakterizacija i biološka aktivnost novihorganorutenijum(II) kompleksa sa estrima (S,S)-etandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline (metil, etil, n-propil, n-butil, izobutil i izopentil), opšteformule [(η6-p-cimen)RuCl{(S,S)-R2eddchxp}]PF6.Polazna kiselina je dobijena u reakciji (S)-2-amino-3-cikloheksilpropanskekiseline i 1,3-dibrompropana u vodenom rastvoru, dok je njena esterifikacija izvršenapomoću tionil-hlorida i odgovarajućeg alkohola. Jodido kompleksi platine(II) sudobijeni reakcijom kalijum-tetrahloridoplatinata(II) i odgovarajućih estara, uz dodatakkalijum-jodida, dok su odgovarajući rutenijum(II) kompleksi sintetisani u reakcijiizmeđu [(η6-p-cimen)RuCl2]2 i estara (S,S)-etandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline.Karakterizacija liganada je urađena klasičnim metodama: elementalnomanalizom, IC, (1H i 13C) NMR spektroskopijom i masenom spektrometrijom, dok sukompleksi pored navedenih metoda, okarakterisani i elektronskom apsorpcionomspektroskopijom, rendgenskom strukturnom analizom za kompleks [(η6-pcimen)RuCl{(S,S)-iBu2eddchxp}]PF6 i 195Pt NMR spektroskopijom za kompleks[PtI2{(S,S)-iBu2pddchxp}]. Na osnovu rezultata dobijenih karakterizacijom, utvrđeno jeda kompleksi platine(II) imaju kvadratno-planarnu strukturu, sa N,N’ bidentatnovezanim estarskim ligandima. Na osnovu rendgenske-strukturne analize kompleksa[(η6-p-cimen)RuCl{(S,S)-iBu2eddchxp}]PF6, potvrđena je pseudo-oktaedarskageometrija sintetisanih Ru(II) kompleksa, sa koordinacijom estarskog liganda preko... AB - In this work, the synthesis, characterization and biological activity of novel(S,S)-1,3-propanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid, its esters (methyl,ethyl, n-propyl, n-butyl, i-butyl, n-pentyl and i-pentyl) and corresponding square-planariodido Pt(II) complexes, of general formula [PtI2{(S,S)-R2pddchxp}], are presented. Inaddition, the synthesis, characterization and biological activity of novelorganorutenium(II) complexes with esters of (S,S)-ethanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid (methyl, ethyl, n-propyl, n-butyl, i-butyl and i-pentyl),general formula, of [(η6-p-cimen)RuCl{(S,S)-R2eddchxp}]PF6, were reported.Starting acid was obtained by reaction of (S)-2-amino-3-cyclohexyl-propanoicacid and 1,3-dibromopropane, in water solution, while esterification was performedwith thionyl chloride and corresponding alcohol. Iodido complexes of platinum(II) wereobtained by reaction of potassium tetrachloridoplatinate(II) and synthesized esters, withadding of potassium iodide. Ruthenium(II) complexes were synthesized by reactionbetween [(η6-p-cymene)RuCl2]2 and different esters of (S,S)-ethanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid. Ligands were characterized by elemental analysis, IR,(1H and 13C) NMR spectroscopy and mass spectrometry, while the complexes, inaddition to these methods, were characterized and UV/Vis, single crystal X-raystructure diffraction analysis for [(η6-p-cymene)RuCl{(S,S)-iBu2eddchxp}]PF6 and 195PtNMR spectroscopy for [PtI2{(S,S)-iBu2pddchxp}]. Based on these results, it is foundthat complexes platinum(II) have square-planar geometry with coordination of ligandsvia nitrogen donor atoms of ester ligands. Single crystal X-ray structure diffractionanalysis of [(η6-p-cymene)RuCl{(S,S)-iBu2eddchxp}]PF6 showed the usual piano-stoolgeometry of complexes, with N,N’ coordination of ester ligands. The stability of thecomplexes of platinum and ruthenium in different solvents was investigated, as well asthe ability of these complexes to bind lysozyme... PB - Универзитет у Београду, Хемијски факултет T2 - Универзитет у Београду T1 - Kompleksi platine(II) i rutenijuma(II) sa diaminskim ligandima: sinteza, karakterizacija i citotoksičnost T1 - COMPLEXES OF PLATINUM(II) ANDRUTHENIUM(II) WITH DIAMINELIGANDS: SYNTHESIS,CHARACTERIZATION ANDCITOTOXICITY UR - https://hdl.handle.net/21.15107/rcub_nardus_6385 ER -
@phdthesis{ author = "Savić, Aleksandar", year = "2014", abstract = "U ovom radu su opisani sinteza, karakterizacija i biološka aktivnost nove (S,S)-1,3-propandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline i njenih estara (metil,etil, n-propil, n-butil, izobutil, n-pentil i izopentil), koji su korišćeni za sintezukvadratno-planarnih Pt(II) jodido kompleksa, opšte formule [PtI2{(S,S)-R2pddchxp}].Takođe je opisana sinteza, karakterizacija i biološka aktivnost novihorganorutenijum(II) kompleksa sa estrima (S,S)-etandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline (metil, etil, n-propil, n-butil, izobutil i izopentil), opšteformule [(η6-p-cimen)RuCl{(S,S)-R2eddchxp}]PF6.Polazna kiselina je dobijena u reakciji (S)-2-amino-3-cikloheksilpropanskekiseline i 1,3-dibrompropana u vodenom rastvoru, dok je njena esterifikacija izvršenapomoću tionil-hlorida i odgovarajućeg alkohola. Jodido kompleksi platine(II) sudobijeni reakcijom kalijum-tetrahloridoplatinata(II) i odgovarajućih estara, uz dodatakkalijum-jodida, dok su odgovarajući rutenijum(II) kompleksi sintetisani u reakcijiizmeđu [(η6-p-cimen)RuCl2]2 i estara (S,S)-etandiamin-N,N’-di-2-(3-cikloheksil)propanske kiseline.Karakterizacija liganada je urađena klasičnim metodama: elementalnomanalizom, IC, (1H i 13C) NMR spektroskopijom i masenom spektrometrijom, dok sukompleksi pored navedenih metoda, okarakterisani i elektronskom apsorpcionomspektroskopijom, rendgenskom strukturnom analizom za kompleks [(η6-pcimen)RuCl{(S,S)-iBu2eddchxp}]PF6 i 195Pt NMR spektroskopijom za kompleks[PtI2{(S,S)-iBu2pddchxp}]. Na osnovu rezultata dobijenih karakterizacijom, utvrđeno jeda kompleksi platine(II) imaju kvadratno-planarnu strukturu, sa N,N’ bidentatnovezanim estarskim ligandima. Na osnovu rendgenske-strukturne analize kompleksa[(η6-p-cimen)RuCl{(S,S)-iBu2eddchxp}]PF6, potvrđena je pseudo-oktaedarskageometrija sintetisanih Ru(II) kompleksa, sa koordinacijom estarskog liganda preko..., In this work, the synthesis, characterization and biological activity of novel(S,S)-1,3-propanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid, its esters (methyl,ethyl, n-propyl, n-butyl, i-butyl, n-pentyl and i-pentyl) and corresponding square-planariodido Pt(II) complexes, of general formula [PtI2{(S,S)-R2pddchxp}], are presented. Inaddition, the synthesis, characterization and biological activity of novelorganorutenium(II) complexes with esters of (S,S)-ethanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid (methyl, ethyl, n-propyl, n-butyl, i-butyl and i-pentyl),general formula, of [(η6-p-cimen)RuCl{(S,S)-R2eddchxp}]PF6, were reported.Starting acid was obtained by reaction of (S)-2-amino-3-cyclohexyl-propanoicacid and 1,3-dibromopropane, in water solution, while esterification was performedwith thionyl chloride and corresponding alcohol. Iodido complexes of platinum(II) wereobtained by reaction of potassium tetrachloridoplatinate(II) and synthesized esters, withadding of potassium iodide. Ruthenium(II) complexes were synthesized by reactionbetween [(η6-p-cymene)RuCl2]2 and different esters of (S,S)-ethanediamine-N,N’-di-2-(3-cyclohexyl)propanoic acid. Ligands were characterized by elemental analysis, IR,(1H and 13C) NMR spectroscopy and mass spectrometry, while the complexes, inaddition to these methods, were characterized and UV/Vis, single crystal X-raystructure diffraction analysis for [(η6-p-cymene)RuCl{(S,S)-iBu2eddchxp}]PF6 and 195PtNMR spectroscopy for [PtI2{(S,S)-iBu2pddchxp}]. Based on these results, it is foundthat complexes platinum(II) have square-planar geometry with coordination of ligandsvia nitrogen donor atoms of ester ligands. Single crystal X-ray structure diffractionanalysis of [(η6-p-cymene)RuCl{(S,S)-iBu2eddchxp}]PF6 showed the usual piano-stoolgeometry of complexes, with N,N’ coordination of ester ligands. The stability of thecomplexes of platinum and ruthenium in different solvents was investigated, as well asthe ability of these complexes to bind lysozyme...", publisher = "Универзитет у Београду, Хемијски факултет", journal = "Универзитет у Београду", title = "Kompleksi platine(II) i rutenijuma(II) sa diaminskim ligandima: sinteza, karakterizacija i citotoksičnost, COMPLEXES OF PLATINUM(II) ANDRUTHENIUM(II) WITH DIAMINELIGANDS: SYNTHESIS,CHARACTERIZATION ANDCITOTOXICITY", url = "https://hdl.handle.net/21.15107/rcub_nardus_6385" }
Savić, A.. (2014). Kompleksi platine(II) i rutenijuma(II) sa diaminskim ligandima: sinteza, karakterizacija i citotoksičnost. in Универзитет у Београду Универзитет у Београду, Хемијски факултет.. https://hdl.handle.net/21.15107/rcub_nardus_6385
Savić A. Kompleksi platine(II) i rutenijuma(II) sa diaminskim ligandima: sinteza, karakterizacija i citotoksičnost. in Универзитет у Београду. 2014;. https://hdl.handle.net/21.15107/rcub_nardus_6385 .
Savić, Aleksandar, "Kompleksi platine(II) i rutenijuma(II) sa diaminskim ligandima: sinteza, karakterizacija i citotoksičnost" in Универзитет у Београду (2014), https://hdl.handle.net/21.15107/rcub_nardus_6385 .