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1.
Eur J Med Chem ; 95: 464-72, 2015 May 05.
Artículo en Inglés | MEDLINE | ID: mdl-25841201

RESUMEN

Two new gold(I) complexes that contain tri-ter-butylphosphine and dialkyl dithiocarbamate ligands were synthesized and characterized by FTIR, NMR spectroscopy, Cyclic voltammetry, elemental analysis and X-ray diffraction. The in vitro cytotoxicity of both complexes was examined against A549 (lung cancer), MCF7 (breast cancer), and HeLa (cervical cancer) human cancer cell lines. Both complexes exhibit very strong in vitro cytotoxic effects against A549, MCF7 and HeLa cell lines. The screening of the cytotoxic activity based on IC50 data against the A549, MCF7, and HeLa lines shows that the synthesized gold(I) complexes are highly effective, particularly against HeLa cancer cell line. Based on IC50 data, the cytotoxic activity of both complexes is better than well-known commercial anticancer drug cisplatin against all the three cancer lines tested.


Asunto(s)
Antineoplásicos/síntesis química , Antineoplásicos/farmacología , Oro/química , Compuestos Organometálicos/síntesis química , Compuestos Organometálicos/farmacología , Fosfinas/química , Tiocarbamatos/química , Antineoplásicos/química , Línea Celular Tumoral , Técnicas de Química Sintética , Diseño de Fármacos , Ensayos de Selección de Medicamentos Antitumorales , Electroquímica , Humanos , Ligandos , Compuestos Organometálicos/química
2.
Biometals ; 27(6): 1115-36, 2014 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-25034122

RESUMEN

The gold(III) complexes of the type [(DACH)Au(en)]Cl3, 1,2-Diaminocyclohexane ethylenediamine gold(III) chloride [where 1,2-DACH = cis-, trans-1,2- and S,S-1,2diaminocyclohexane and en = ethylenediamine] have been synthesized and characterized using various analytical and spectroscopic techniques including elemental analysis, UV-Vis and FTIR spectra; and solution as well as solid-state NMR measurements. The solid-state (13)C NMR shows that 1,2-diaminocyclohexane (1,2-DACH) and ethylenediamine (en) are strongly bound to the gold(III) center via N donor atoms. The stability of the mixed diamine ligand gold(III) was determined by (1)H and (13)C NMR spectra. Their electrochemical behavior was studied by cyclic voltammetry. The structural details and relative stabilities of the four possible isomers of the complexes were also reported at the B3LYP/LANL2DZ level of theory. The coordination sphere of these complexes around gold(III) center adopts distorted square planar geometry. The computational study also demonstrates that trans- conformations is slightly more stable than the cis-conformations. The antiproliferative effects and cytotoxic properties of the mixed diamine ligand gold(III) complexes were evaluated in vitro on human gastric SGC7901 and prostate PC3 cancer cells using MTT assay. The antiproliferative study of the gold(III) complexes on PC3 and SGC7901 cells indicate that complex 1 is the most effective antiproliferative agent among mixed ligand based gold(III) complexes 1-3. The IC50 data reveal that the in vitro cytotoxicity of complexes 1 and 3 against SGC7901 cancer cells are fairly better than that of cisplatin.


Asunto(s)
Ciclohexilaminas/química , Diaminas/química , Compuestos de Oro/química , Antineoplásicos/farmacología , Carcinoma/patología , División Celular/efectos de los fármacos , Línea Celular Tumoral , Biología Computacional , Diaminas/síntesis química , Diaminas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Electroquímica , Compuestos de Oro/síntesis química , Compuestos de Oro/farmacología , Humanos , Concentración 50 Inhibidora , Masculino , Conformación Molecular , Resonancia Magnética Nuclear Biomolecular , Neoplasias de la Próstata/patología , Espectrofotometría Ultravioleta , Espectroscopía Infrarroja por Transformada de Fourier , Neoplasias Gástricas/patología
3.
Artículo en Inglés | MEDLINE | ID: mdl-23876928

RESUMEN

Recent advances in oncology are focused on developing new complexes of gold(III) with various ligands that show augmented anti-proliferative potential and reduced toxicity as compared to cis-platin. In this study, new Au(III) complexes of the type [(thione)2Au(diamine)]Cl3 are reported, where thione=1,3-imidazolidine-2-thione (Imt), 1,3-Diazinane-2-thione (Diaz) and diamine=1,2-diaminoethane (en), 1,3-diaminopropane (pn) or 1,4-diaminobutane (bn). The solid state IR as well as (13)C and (15)N NMR data indicate that Au(III) center is bonded via sulfur of thiocarbonyl SC site of the thiones and also chelated by the diamines from the trans side of coordinated thiones. Spectroscopic data are evaluated by comparisons with calculated data from the built and optimized structure by GAUSSIAN 09 at the RB3LYP level with LanL2DZ bases set. These new Au(III) complexes based on mixed thione and diamine ligands are very similar to the square planar structure of tetracoordinate [Au(en)2]Cl3complex. In this study, cytotoxicity data for these gold(III) complexes against C6 glioma cell lines are also reported, and the results indicate some complexes have cytotoxicity comparable to cis-platin.


Asunto(s)
Aminas/síntesis química , Aminas/farmacología , Modelos Moleculares , Tionas/síntesis química , Tionas/farmacología , Aminas/química , Animales , Muerte Celular/efectos de los fármacos , Línea Celular Tumoral , Oro/química , Oro/farmacología , Concentración 50 Inhibidora , Ligandos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Ratas , Soluciones , Espectrofotometría Infrarroja , Tionas/química , Torsión Mecánica
4.
Bioinorg Chem Appl ; 2013: 476874, 2013.
Artículo en Inglés | MEDLINE | ID: mdl-23533372

RESUMEN

The synthesis and characterization of cadmium and mercury complexes of selenocyanate of the type [(L)M(SeCN)2] are described, where L is L-Histidine (His) or L-Glycine (Gly) and M is Cd(2+) or Hg(2+). These complexes are obtained by the reaction of 1 equivalent of respective amino acids with metal diselenocyanate precursor in a mixture of solvents (methanol : water = 1 : 1). These synthesized compounds are characterized by analytical and various spectroscopic techniques such as elemental analysis (EA), IR, H,1 and C13 NMR in solution and in the solid state for C13 and N15. The in vitro antibacterial activities of these complexes have been investigated with standard type cultures of Escherichia coli (MTCC 443), Klebsiella pneumoniae (MTCC 109), Pseudomonas aeruginosa (MTCC 1688), Salmonella typhi (MTCC 733), and Staphylococcus aureus (MTCC 737).

5.
Spectrochim Acta A Mol Biomol Spectrosc ; 79(5): 1196-201, 2011 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-21680234

RESUMEN

Two Au(III) complexes of the type [Au(en)2]Cl3 (2a) and [Au(N-pr-en)2]Cl3 (3a) were synthesized by reacting Auric acid (HAuCl(4)·3H2O) with 2 equiv. ethylenediamine (en) or N-alkyl substituted ethylenediamine ligands. This metallodrug was characterized by various analytical and spectroscopic techniques such as elemental analysis, UV-Vis, Far-IR, 1H NMR and solution 13C as well as solid 13C and 15N NMR. Potentiality of [Au(en)2]Cl3 and [Au(N-pr-en)2]Cl3 as an anti-cancer agent were investigated by measuring some relevant physicochemical and biochemical properties such as stability of Au-N bonds by vibrational stretching from Far IR as well as cytotoxicity and stomach cancer cell inhibiting effect, respectively. The solid-state 15N NMR chemical shift shows that the ligand is strongly bound to gold(III) centre via N atoms. The computational study of 2a shows that the gold coordination sphere adopts distorted square planar geometry with bidentate ethylenediamine ligands acting as a tetradentate chelate. While stable in the solution state, the in vitro biological studies performed with these compounds 2a in solution showed higher activity towards the inhibitory effects of the human cancer cell lines such as prostate cancer (PC-3) and gastric carcinoma (SGC-7901) than that of the N-substituted gold(III) complex (3a). Cytotoxicity of the new compounds has also been estimated in PC-3 and SGC-7901 cells.


Asunto(s)
Antineoplásicos/síntesis química , Antineoplásicos/farmacología , Compuestos de Oro/síntesis química , Compuestos de Oro/farmacología , Neoplasias de la Próstata/tratamiento farmacológico , Neoplasias Gástricas/tratamiento farmacológico , Etilenodiaminas/química , Humanos , Espectroscopía de Resonancia Magnética , Masculino , Modelos Moleculares , Células Tumorales Cultivadas
6.
Artículo en Inglés | MEDLINE | ID: mdl-19010714

RESUMEN

Cadmium(II)cyanide complexes of various thiones (imidazolidine-2-thione, diazinane-2-thione and their derivatives) have been prepared and characterized by elemental analysis, IR and solid as well as solution NMR spectroscopy. It appears from the IR data that all complexes are non-ionic [(>C=S)(2)Cd(CN)(2)]. An upfield shift in the (13)C NMR and downfield shifts in the (1)H NMR are consistent with the sulfur coordination to cadmium(II). The solid (113)Cd NMR data show the presence of different coordination numbers in some complexes.


Asunto(s)
Cianuros/química , Compuestos Organometálicos/química , Tionas/química , Dimetilsulfóxido , Espectroscopía de Resonancia Magnética , Soluciones , Espectrofotometría Infrarroja
7.
Artículo en Inglés | MEDLINE | ID: mdl-16843708

RESUMEN

Silver(I) complexes of several thiolates have been prepared. These complexes have been characterized by elemental analysis and 13C NMR spectroscopy. All the Ag(I)-thiolate complexes are polymeric in nature. Therefore, 13C CP MAS NMR is being used extensively to analyze the binding site of the ligand and the nature of complexation. A significant shift difference was observed for S binding site whereas smaller shift was observed for carboxylate binding site. The antimicrobial activities for Ag(I)-glutathione complex was measured and compared with Ag(I)-captopril complex.


Asunto(s)
Antiinfecciosos , Bacterias/crecimiento & desarrollo , Compuestos Organometálicos , Plata/química , Compuestos de Sulfhidrilo , Antiinfecciosos/síntesis química , Antiinfecciosos/química , Antiinfecciosos/farmacología , Captopril/química , Captopril/farmacología , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Compuestos Organometálicos/síntesis química , Compuestos Organometálicos/química , Compuestos Organometálicos/farmacología , Compuestos de Sulfhidrilo/síntesis química , Compuestos de Sulfhidrilo/química , Compuestos de Sulfhidrilo/farmacología
8.
Spectrochim Acta A Mol Biomol Spectrosc ; 62(4-5): 880-5, 2005 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-15950525

RESUMEN

Cadmium(II) complexes of Imidazolidine-2-selenone (ImSe) and its derivatives have been prepared with the general formula Cd(RImSe)2Cl2 (where R=Me, Et, Pr, etc.). These complexes are characterized by elemental analysis, IR and NMR (1H, 13C, 77Se and 113Cd) spectroscopy. An upfield shift in C=Se resonance of selenones in 13C NMR and in 77Se and high-frequency shifts in N-H resonances in 1H are consistent with the selenium coordination to Cd(II). The 77Se nucleus in Cd(ImSe)2Cl2 is shielded by 38 ppm on coordination, relative to the free ligand. The principal components of the 77Se, 113Cd and 13C shielding tensors for the complexes were determined from solid-state NMR data. Large selenium chemical shift anisotropies were observed for these complexes.


Asunto(s)
Cadmio/química , Selenio/química , Anisotropía , Ligandos , Espectroscopía de Resonancia Magnética , Soluciones/química , Espectroscopía Infrarroja por Transformada de Fourier
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