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Valentin, Valentin; Ključarić, Valentina
09/2016Web Resource
U ovom doktorskom radu sintetizirani su Cu(II) molekulski kompleksi Cu(1-TsC-N3)2Cl2 i Cu(1-MsC-N3)2Cl2 biološki aktivnih N-sulfonilcitozinskih (C) liganada s tosilom (Ts) i mezilom (Ms) te novi ciklam-TsC konjugati. Mannichova reakcija TsC liganda, paraformaldehida i ciklama u prisutnosti octene kiseline daje C-aminometilirani konjugat u kojem je ciklam vezan preko metilenskog mosta na C5 položaj citozina. Ista reakcija sa zaštićenim ciklamom daje C4 aminometilirani produkt. Pomoću ESI-MS metode provedena je studija stabilnosti i utjecaja biološki važnih metalnih iona (Na+, K+, Ca2+, Mg2+, Zn2+, Cu2+) na ligande, Cu(II) komplekse, te na poliaza makrocikličke konjugate. U interakciji s ligandima i Cu(II) kompleksima alkalijski metali uslijed elektrostatskih interakcija stvaraju klastere, dok je nastanak bis i tris te miješanih kompleksa uočen u interakciji s Ca2+ i Mg2+. Interakcija Zn2+ s ligandima i Cu(II) kompleksima rezultira nastankom monometalnih kompleksa kao i dimetalnih kompleksa zbog afniteta Zn2+ prema atomima kisika i dušika koji u strukturu uključuju molekule vode. Novi poliaza makrociklički konjugati u interakciji s CuCl2 stvaraju molekulske komplekse u kojima je CuCl2 u ciklamskom prstenu, a u interakciji s ZnSO4 nastaju ionski kompleksi u kojima je Zn2+ smješten u ciklamskom prstenu. Abstract In this doctoral thesis, Cu (II) molecular complexes Cu(1-TsC-N3)2Cl2 and Cu(1-MsC-N3)2Cl2 of biologically active N-sulfonylcytosine ligands (C) with tosyl (Ts) and mesyl (Ms) and new cyclame-TsC conjugates were synthesized. The Mannich reaction of TsC, paraformaldehyde and cyclame in the presence of acetic acid yields C-aminomethylated konjugate in which the cyclame was introduced through a methylene bridge at C5 position of cytosine. The same reaction with protected cyclame gives C4 aminomethylated product. Using ESI-MS method was conducted stability studies and the influence of biologically important metal ions (Na+, K+, Ca2+, Mg2+, Zn2+, Cu2+) to ligands, Cu (II) complexes, and polyaza macrocyclic conjugates. The interaction of ligands and Cu (II) complexes with biologically important metal ions results with formation of various metal complex. Alkali metals Na+ and K+ formed clusters due to the electrostatic inetractions. Bis, tris and mixed ligand complexes were observed upon mixing with Ca2+ or Mg2+ salt. Interaction with Zn2+ sieed monometal Zn2+ complexes and mixed ligand dimetal complexes that includ water molecules in the structures of the complexes because of affinity of Zn2+ for both O and N atoms. Both ions Cu2+ and Zn2+ were located within the cyclamic ring upon their interaction with polyaza macrocyclic conjugates. Newly formed Cu2+complexes were molecular while the ionic complexes were formed with zinc ions.
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