Water-soluble and water-stable Gold(I), Gold(II) and Gold(III) phosphine complexes: The early years

Mohr, Fabian; Sanzb, Sergio; Vergarab, Elena; Cerrada, Elena; Laguna, Mariano

doi:10.1007/bf03215556

Cited by 23 publications

(10 citation statements)

References 29 publications

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“…NMR spectra were recorded with Bruker Avance 200 (operating at 200.13, 50.33 and 81.01 MHz for 1 H, 13 C and 31 P, respectively) and Bruker Avance 400 (operating at 400.13, 100.63 and 162.00 MHz for 1 H, 13 C and 31 P, respectively) instruments at room temperature. Deuterated chloroform was used as the NMR solvent and 1 H and 13 C{ 1 H} NMR spectra were referenced to residual solvent resonances (7.26 ppm and 77.16 ppm, respectively), whereas 31 P{ 1 H} NMR spectra were referenced to external H 3 PO 4 . The mass spectra were recorded using SSQ 10 or MAT95XL, using ESI-or DEI-ionization.…”

Section: Structural and Purity Determinationmentioning

confidence: 99%

“…1 H-NMR (200 MHz, CDCl 3 ): d 0.07 (6H, s, Si(CH 3 ) 2 ), 0.88 (9H, s, C(CH 3 ) 3 ), 1.38 (2H, t, SH, 3 J HH 8.5 Hz) 2.71 (4H, m, S-CH 2 ), 3.80 (1H,m, CH). 13 C{ 1 H}-NMR (50 MHz, CDCl 3 ): d -4.5 (Si(CH 3 ) 2 ), 18.0 (C(CH 3 ) 3 ), 25.8 (C(CH 3 ) 3 ), 29.2 (S-CH 2 ), 73.8 (CH).…”

Section: Cis-bis(dppe)(3-ethoxypropane-12-dithiolato)platinum(ii)mentioning

confidence: 99%

“…204 3 J HH(1) 3.82 Hz, 3 J HH(2) 3.88 Hz, OH). 13 3 J CP(A) 6.0 Hz, 3 J CP(B) 5.9 Hz, CH), 45.1 (t, 1 J CP 30.8 Hz, CH 2 ), 39.1 (s, S-CH 2 ). 31…”

Section: Cis-bis(dppm)(3-hydroxypropane-12-dithiolato)platinum(ii) 11mentioning

confidence: 99%

“…The mixture was heated to 78 • C for 6 h. Upon cooling down to room temperature the product precipitated as pale yellow powder. After filtration the product was washed with a small portion of H 2 O, EtOH and Et 2 O. J HH 9.0 Hz, S-CH 2 ) 13. C{ 1 H} NMR (100 MHz, D 2 O, 25 • C): d 70.3 (m, N-CH 2 -N), 50.3 (d, 3 J CP 11.5 Hz, N-CH 2 -P), 36.6 (m, S-CH 2 ).…”

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confidence: 99%

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Structure, solution chemistry, antiproliferative actions and protein binding properties of non-conventional platinum(ii) compounds with sulfur and phosphorus donors

et al. 2011

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Twelve Pt(II) complexes with cis-PtP(2)S(2) pharmacophores (where P(2) refers to two monodentate or one bidentate phosphane ligand and S(2) is a dithiolato ligand) were prepared, characterized and evaluated as potential antiproliferative agents. The various compounds were first studied from the structural point of view; afterward, their solubility properties as well as their solution behaviour were analyzed in detail. Antiproliferative properties were specifically evaluated against A2780 human ovarian carcinoma cells, either resistant or sensitive to cisplatin. For comparison purposes similar studies were carried out on four parent cis-dichloro bisphosphane Pt(II)complexes. On the whole, the cis-PtP(2)S(2) compounds displayed significant antiproliferative properties while the cis-PtP(2)Cl(2) (cis-dichloro bisphosphane Pt(II)) compounds revealed quite poor biological performances. To gain further insight into the molecular mechanisms of these bisphosphane Pt(II) compounds, the reactions of selected complexes against the model protein cytochrome c were investigated by ESI-MS and their adduct formation explored. A relevant reactivity with cyt c was obtained only for cis-PtP(2)Cl(2) compounds, whereas cis-PtP(2)S(2) compounds turned out to be nearly unreactive. The obtained results are interpreted and discussed in the frame of the current knowledge of anticancer platinum compounds and their structure-activity-relationships. The observation of appreciable antiproliferative effects for the relatively inert cis-PtP(2)S(2) compounds strongly suggests that these compounds will undergo specific activation within the cellular environment.

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Section: Structural and Purity Determinationmentioning

confidence: 99%

Section: Cis-bis(dppe)(3-ethoxypropane-12-dithiolato)platinum(ii)mentioning

confidence: 99%

“…204 3 J HH(1) 3.82 Hz, 3 J HH(2) 3.88 Hz, OH). 13 3 J CP(A) 6.0 Hz, 3 J CP(B) 5.9 Hz, CH), 45.1 (t, 1 J CP 30.8 Hz, CH 2 ), 39.1 (s, S-CH 2 ). 31…”

Section: Cis-bis(dppm)(3-hydroxypropane-12-dithiolato)platinum(ii) 11mentioning

confidence: 99%

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confidence: 99%

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Structure, solution chemistry, antiproliferative actions and protein binding properties of non-conventional platinum(ii) compounds with sulfur and phosphorus donors

et al. 2011

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“…[7][8][9][10] Among the large family of open-cage PTAd erivatives, [2,11] 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) is ar elevant one (Figure 1), [11a, 12] and its binding capacity has been intensively studied for the Cu, Ru, Rh, Pd, Pt, and Au transition metals to produce complexes that are used mainly for biological applications [13][14][15][16] and, to al esser extent, for catalysis. [17][18][19][20] The DAPTAl igand usually exhibits the P-coordination modet ot he metal center, [12][13][14][15][20][21][22][23] and recently,t he N-coordination mode wasa lso reported. [17] Although DAPTAh as two coordination sites from the acetyl oxygen atoms, the O-coordination modeo fD APTAhas not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

Copper(II) and Sodium(I) Complexes based on 3,7‐Diacetyl‐1,3,7‐triaza‐5‐phosphabicyclo[3.3.1]nonane‐5‐oxide: Synthesis, Characterization, and Catalytic Activity

Mahmoud

Silva

Śliwa

et al. 2018

Chemistry An Asian Journal

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The reaction of 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane (DAPTA) with metal salts of Cu or Na /Ni under mild conditions led to the oxidized phosphane derivative 3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane-5-oxide (DAPTA=O) and to the first examples of metal complexes based on the DAPTA=O ligand, that is, [Cu (μ-CH COO) (κO-DAPTA=O)] (1) and [Na(1κOO';2κO-DAPTA=O)(MeOH)] (BPh ) (2). The catalytic activity of 1 was tested in the Henry reaction and for the aerobic 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO)-mediated oxidation of benzyl alcohol. Compound 1 was also evaluated as a model system for the catechol oxidase enzyme by using 3,5-di-tert-butylcatechol as the substrate. The kinetic data fitted the Michaelis-Menten equation and enabled the obtainment of a rate constant for the catalytic reaction; this rate constant is among the highest obtained for this substrate with the use of dinuclear Cu complexes. DFT calculations discarded a bridging mode binding type of the substrate and suggested a mixed-valence Cu /Cu complex intermediate, in which the spin electron density is mostly concentrated at one of the Cu atoms and at the organic ligand.

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Sustainable Micellar Gold Catalysis – Poly(2‐oxazolines) as Versatile Amphiphiles

et al. 2016

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The application of five polymer amphiphiles in the gold‐catalyzed allene cycloisomerizations under aqueous micellar conditions is described. The polymers were prepared by ring‐opening cationic polymerization based on poly(2‐methyl‐2‐oxazoline) as hydrophilic segment and different hydrocarbon‐ or fluorocarbon‐based hydrophobic segments. The catalytic activity in the gold‐catalyzed allene cyclization is strongly dependent on the type of gold precursor, the salt concentration in the bulk aqueous medium, and the concentration of the polymeric amphiphile. Best results were obtained with 2 mol% of gold(III) bromide, 1 mM of amphiphile and 5 M sodium chloride, affording over 80% yield for different heterocyclic products. The catalyst system is also suitable for the dehydrative cyclization of acetylenic diols to furans. Moreover, successful catalyst recycling was demonstrated in three consecutive runs when using optimized extraction conditions.magnified image

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Water-soluble and water-stable Gold(I), Gold(II) and Gold(III) phosphine complexes: The early years

Abstract: This article briefly reviews the still rather limited knowledge of the chemistry, structures, reactions and applications of gold complexes containing water-soluble phosphine ligands sorted by gold oxidation state. Gold Bulletin 2006 • 39/4 212

Cited by 23 publications

References 29 publications

Structure, solution chemistry, antiproliferative actions and protein binding properties of non-conventional platinum(ii) compounds with sulfur and phosphorus donors

Structure, solution chemistry, antiproliferative actions and protein binding properties of non-conventional platinum(ii) compounds with sulfur and phosphorus donors

Copper(II) and Sodium(I) Complexes based on 3,7‐Diacetyl‐1,3,7‐triaza‐5‐phosphabicyclo[3.3.1]nonane‐5‐oxide: Synthesis, Characterization, and Catalytic Activity

Sustainable Micellar Gold Catalysis – Poly(2‐oxazolines) as Versatile Amphiphiles

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