Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Ester

Interactions of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic acid (compound 1) and its mono-Me ester (compound 2) with the human serum albumin (HSA) have been studied by fluorescence spectroscopy. Comp. 1 exerts antiproliferative activity toward human tumor cells and significant selectivity (tumor vs. healthy cells) in vitro. Competitive binding study with warfarin and ibuprofen as binding site probes, revealed that one molecule of comp. 1 selectively binds to HSA Sudlow site I (warfarin site) with moderate binding constant (Kb = (2.8 ± 0.5) x 104 M-1 at 37 ± 1 oC), while comp. 2 binds to Sudlow site II (Kb = (3.2 ± 0.9) x 104 M-1 at 37 ± 1 oC). Fluorescence quenching at different temperatures was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. Energy resonance transfer between HSA and comp. 1 was examined according to Förster’s non-radiative energy transfer theory. Distance of about 10 Å between ligand and Trp214 (HSA) was obtained. Docking studies confirmed HSA Sudlow site I as a preferable comp. 1 binding site, and Sudlow site II as comp. 2 binding site. Molecular dynamics simulations proved the stability of comp. 1/HSA complex

Sinteza, strukturna karakterizacija i citotoksična aktivnost dva nova organorutenijum(II) kompleksa

Two new p-cymene ruthenium(II) complexes containing as additional ligands N-methylpiperazine ([(eta(6)-p-cymene)RuCl2(CH3NH(CH2)(4)NH)]PF6, complex 1) or vitamin K-3-thiosemicarbazone ([(eta(6)-p-cymene)RuCl2(K(3)tsc)], complex 2) were synthesized starting from [(eta(6)-p-cymene)(2)RuCl2](2) and the corresponding ligand. The complexes were characterized by elemental analysis, IR, electronic absorption and NMR spectroscopy. The X-ray crystal structure determination of complex 1 revealed "piano-stool" geometry. The differences in the cytotoxic activity of the two complexes are discussed in terms of the ligand present.Sintetisana su dva nova p-cimen-rutenijum(II) kompleksa koji sadrže kao dodatne ligande N-metilpiperazin ([(h6-p-cimen)RuCl2(CH3NH(CH2)4NH)]PF6, kompleks 1) i vitamin K3-tiosemikarbazon ([(h6-p-cimen)RuCl2(K3tsc)], kompleks 2). Oba nova kompleksa dobijena su polazeći od [(h6-p-cimen)2RuCl2]2 kompleksa i odgovarajućeg liganda. Kompleksi su okarakterisani elementalnom analizom, IC, elektronsko-apsorpcionom i NMR spektroskopijom. Rendgeno-strukturna analiza kompleksa 1 pokazala je “piano-stool” geometriju. U zavisnosti od prisutnog liganda diskutovana je razlika u citotoksičnoj aktivnosti ova dva dobijena kompleksa

Supplementary data for article: Pantelić, N. Đ.; Zmejkovski, B. B.; Trifunović-Macedoljan, J.; Savić, A.; Stanković, D.; Damjanović, A.; Juranic, Z.; Kaluđerović, G. N.; Sabo, T. Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N ’-Diacetate. Journal of Inorganic Biochemistry 2013, 128, 146–153. https://doi.org/10.1016/j.jinorgbio.2013.08.002

Supplementary material for: [https://doi.org/10.1016/j.jinorgbio.2013.08.002]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1422

Struktura i stereohemija poli-(1-naftilamina) elektrohemijski sintetisanog u neutralnom acetonitrilnom rastvoru

Poly-(1-naphthylamine) films were synthesized potentiodinamically and potentiostatically from 1-naphthylamine in neutral acetonitrile medium using a platinum electrode. These polymer films were investigated by infrared spectroscopy. Contrary to earlier published results neglecting the stereochemistry of the poly-(1-naphthylamine), we predict on the basis of quantum stereochemical analysis of the possible structural subunits of the polymer, that the ordinary N–C(4) coupled product is not predominant in the polymer because it is far removed from the expected planarity. Based on the results of IR investigations and semiempirical quantum chemical calculations, it is proposed that the polymer products are formed via mixed N–C(4), N–C(5) and N–C(7) coupling routes. The heats of formation of the oxidized 1-naphthylamine dimers and hexamers were calculated.Poli-(1-naftilaminski) filmovi sintetisani su potenciostatski i potenciodinamički iz neutralnog acetonitrilnog rastvora 1-naftilamina na platinskoj elektrodi. Ovi polimerni filmovi ispitivani su IR spektroskopijom. Za razliku od ranije publikovanih rezultata koji su zanemarivali stereohemiju poli-1(-naftilamina), u ovom radu se predviđa na osnovu kvantne stereohemijske analize mogućih strukturnih jedinica polimera da uobičajeni N–C(4) kuplovani produkt nije predominantan u polimeru, jer njegova struktura nije planarna. Na osnovu rezultata IR ispitivanja i semiempirijskih kvantno-hemijskih proračuna mi pretpostavljeno je da se polimerni produkti formiraju kombinovanim N–C(4), N–C(5) i N–C(7) načinima vezivanja 1-naftilamina. U ovom radu su takođe izračunate toplote nastajanja oksidovanih dimera i heksamera 1-naftilamina

Investigation of the effect of the aminocarboxylato chelate conformation on the optical activity of the cis(NO2),trans(NH2) -bis(aminocarboxylato)dinitrocobalt/ate(III) isomers

In the cis(NO2),trans(NH2)-bis(aminocarboxylato) dinitrocobalt/ate(III) isomers, containing glycinato, S-alaninato, S-n-valinato, S-valinato, S-n-leucinato, S-leucinato, S-i-leucinato and S-arginine ligands, respectively, it was found that in the Δ-isomers circular dichroic spectra are determined by the configurational contribution to the optical activity. This is connected in the case of optically active ligands with the chair conformation of the chelate rings and the equatorial position of the ring side group. In the Δ-isomers, λ- conformation of the aminocarboxylato chelate rings and the axial position of the ring side groups induce a considerable contribution to the optical activity, which varies from complex to complex. NMR spectroscopy showed that these variations are related to small changes in the chelate ring conformation in such a way that a more axial position of a ring side group induces a larger contribution. The λ-conformation of a S-aminocarboxylato chelate ring induces a large negative contribution to the circular dichroism of the investigated complexes. © 1988

Supplementary data for article: Pantelić, N. Đ.; Zmejkovski, B. B.; Trifunović-Macedoljan, J.; Savić, A.; Stanković, D.; Damjanović, A.; Juranic, Z.; Kaluđerović, G. N.; Sabo, T. Gold(III) Complexes with Esters of Cyclohexyl-Functionalized Ethylenediamine-N,N ’-Diacetate. Journal of Inorganic Biochemistry 2013, 128, 146–153. https://doi.org/10.1016/j.jinorgbio.2013.08.002

Supplementary material for: [https://doi.org/10.1016/j.jinorgbio.2013.08.002]Related to published version: [http://cherry.chem.bg.ac.rs/handle/123456789/1422

A kinetic investigation of the tris(4-morpholinecarbodithionato-S,S') cobalt(III) complex formation by the intralattice and interlattice reactions

The kinetics of tris-(4-morpholinecarbodithionato-S,S) cobalt(III) formation by the intralattice and interlattice reactions of hexaaminecobalt(III) cation with dithiocarbamato anion was investigated under isothermal conditions. The intralattice reaction, conducted in the solid hexaaminecobalt(III) 4-morpholinecarbodithionate salt, proceeded well at temperatures of 50-80°C, conforming to the phase boundary Rn reaction mechanism (Ea = 92.6 kJ mol-1, A = 5.28 × 109 s-1). The interlattice reaction, conducted in the mixture of hexaaminecobalt(III) chloride and potassium 4-morpholinecarbodithionate powders, proceeded well at temperatures of 140-200° C. The effect of the particle size of the powders and of the powder packing pressure on the kinetic parameters were also investigated. In the first half of the reaction, the random nucleation F1 mechanism seems to operate (Ea = 200-265 kJ mol-1, A = 8.6 × 1018-3.6 × 1027s-1); later the diffusional mechanism prevails. In addition, a fast initial process in the interlattice reaction has been discovered and investigated at lower temperatures (80-115° C). It conforms to the random nucleation F1 reaction mechanism (Ea = 63 kJ mol-1, A = 1.6 × 105 s-1). © 1993