Crystal structure and solution chemistry of the cytotoxic complex 1,2-dichloro(o-phenanthroline)gold(III) chloride

Abbate, Francesco; Orioli, Pierluigi; Bruni, B; Marcon, Giordana; Messori, Luigi

doi:10.1016/s0020-1693(00)00299-1

Cited by 86 publications

(51 citation statements)

References 13 publications

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“…NaAuCl 4 ·2H 2 O, ethylenediamine, D 2 O, and dmso-d 6 were purchased from Aldrich Chemical Co. and used as received. H 2 (5'-GMP) and Na 2 (5'-GMP) were purchased from Sigma and used as received.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Structures, and Electrochemistry of Gold(III) Ethylenediamine Complexes and Interactions with Guanosine 5‘-Monophosphate

et al. 2006

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Abstract[Au(en)Cl 2 ]Cl·2H 2 O has been synthesized and its structure has been solved for the first time by the single crystal X-ray diffraction method. The complex has square planar geometry about the Au(III) and the anionic Cl − is located in the apical position and at a distance of 3.3033(10) Å compared to 2.2811 (9) 3+ . 1 H, 13 C, and 31 P NMR reveal that in aqueous solution [Au(en)Cl 2 ] + bonds to guanosine 5'-monophosphate, 5'-GMP, (1:1 mole ratio) via N7, although the stability is not very high. NMR data also indicate that N7-O6 or N7-phosphate 5'-GMP chelation, as found in some Au(III)-nucleotide complexes, is not present. The Au(III) complex undergoes hydrolysis at pH > 2.5−3.0 and, therefore N1 coordination to 5'-GMP is not observed. No direct coordination between 5'-GMP and [Au(en) 2 ]Cl 3 is observed. KeywordsGold(III); guanosine 5'-monophosphate; NMR; cyclic voltammetry; X-ray structure Gold(III) complexes are isoelectronic and generally isostructural to platinum(II) complexes, and therefore it is anticipated that they will have similar activity to the Pt(II) antitumor drugs.1-5 However, compared to the corresponding Pt(II) complexes, Au(III) complexes have not been well explored chemically or electrochemically, possibly because few gold(III) complexes have been shown to be sufficiently stable in aqueous solution.6,7Ethylenediamine (en) is a common chelating ligand that is widely used in transition metal complexes. Its gold complexes have been known since 1931,8-10 Methods and Materials MaterialsNaAuCl 4 ·2H 2 O, ethylenediamine, D 2 O, and dmso-d 6 were purchased from Aldrich Chemical Co. and used as received. H 2 (5'-GMP) and Na 2 (5'-GMP) were purchased from Sigma and used as received. All solutions other than those for NMR measurements were prepared using deionized water that was purified with a Barnstead NANOpure cartridge system (18 MΩ). Nucleotide Stock Solutions-Na 2 (5'-GMP) or H 2 (5'-GMP) was dissolved in H 2 O or D 2 O and the concentration of the nucleotide was determined by UV spectroscopy (λ max 252 nm; ε = 1.37 × 10 4 M −1 cm −1 ; pH 7). The required amount of Au(III) compound was added to the 5'-GMP solution. Syntheses MethodsThermogravimetric Analysis-Measurements were made on a Shimadzu TGA-50 analyzer under N 2 atmosphere with a flow rate of 20 mL min −1 in a Pt cell. Samples weighed 3−7 mg. The temperature increased at 20 °C min −1 from room temperature to 900°C .NMR-Spectra were obtained in D 2 O on a Varian Inova 500 MHz in D 2 O. The temperature dependent 1 H studies were referenced to internal tetramethylammonium ion at 3.185 ppm and the spectra at 26 °C were referenced to the HOD line at 4.800 ppm (The TMA + resonance is very near that of ethylenediamine and can overlap at times). 31 P spectra were referenced to external 85 % H 3 PO 4 and 13 C spectra to DSS. pD = pH (meter reading) + 0.40.Electrochemical Measurements-A CHI 832 workstation (CH Instruments, Inc.) was used to collect electrochemical data. Experiments were performed at room temperature (20 ± 1 °C) in ...

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Section: Methodsmentioning

confidence: 99%

Synthesis, Structures, and Electrochemistry of Gold(III) Ethylenediamine Complexes and Interactions with Guanosine 5‘-Monophosphate

et al. 2006

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“…Abbate and co-workers (2000) reported that the biological properties of [Au(phen)Cl 2 ]Cl might be derived, at least partially, from free phenanthroline 27 . Studies showed that both metal-free phen and metal-phen complexes affected mitochondrial function, retarded synthesis of cytochromes b and c, and uncoupled cellular respiration 30 …”

Section: Discussionmentioning

confidence: 99%

Studies on the cytotoxic, apoptotic and antitumoral effects of Au(III) and Pt(II) complexes of 1, 10-phenanthroline on V79 379A and A549 cell lines

Bostancıoğlu

Işık

Genç

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…formed in aqueous solutions [17,18]. This complex formation reduces the formal potential from the Nernst equation, and thus the reduction of gold(III) by dl--tocopherol tends not to occur.…”

Section: +mentioning

confidence: 99%

<i>In Situ</i> Microscope Measurements of the Formation of Nanometer-Sized Gold Particles at the Dodecane/Water Interface through the Direct Reduction of Aqueous Tetrachloroaurate(III) by Hydrophobic <i>dl</i>-α-Tocopherol in the Presence of 1,10-Phenanthroline

Tsukahara

Kobayashi

Fujiwara

2014

SERDJ

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The contact of a dodecane solution of hydrophobic dl--tocopherol with an aqueous solution of tetrachloroaurate(III) resulted in the direct reduction of tetrachloroaurate(III) and the formation of gold particles at the dodecane/water interface. Without other additives, the gold particles were unfavorably aggregated with each other and chains of gold particles were formed. In the present study, a chemical preventing the aggregation was sought. Fourteen types of chemicals were individually added to the two-phase system, and then the size, shape, and movements of the gold particles formed at the dodecane/water interface were observed through an optical microscope using bright-field illumination, using dark-field illumination, or with scattered laser light under total internal reflection conditions. Of the 14 chemicals, 1,10-phenanthroline (phen) effectively prevented the aggregation of gold particles at the interface. The gold particles formed in the presence of phen under the optimized conditions were recovered on a coverslip, and their size and shape were recorded using an atomic force microscope. Almost all of the recovered gold particles were not higher than 50 nm and this meant that nanometer-sized gold particles were formed.

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Crystal structure and solution chemistry of the cytotoxic complex 1,2-dichloro(o-phenanthroline)gold(III) chloride

Cited by 86 publications

References 13 publications

Synthesis, Structures, and Electrochemistry of Gold(III) Ethylenediamine Complexes and Interactions with Guanosine 5‘-Monophosphate

Synthesis, Structures, and Electrochemistry of Gold(III) Ethylenediamine Complexes and Interactions with Guanosine 5‘-Monophosphate

Studies on the cytotoxic, apoptotic and antitumoral effects of Au(III) and Pt(II) complexes of 1, 10-phenanthroline on V79 379A and A549 cell lines

<i>In Situ</i> Microscope Measurements of the Formation of Nanometer-Sized Gold Particles at the Dodecane/Water Interface through the Direct Reduction of Aqueous Tetrachloroaurate(III) by Hydrophobic <i>dl</i>-α-Tocopherol in the Presence of 1,10-Phenanthroline

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