Transition‐Metal Complexes Based on a Sulfonate‐Containing N‐Donor Ligand and Their Use as HIV Antiviral Agents

García‐Gallego, Sandra; Serramía, Ma Jesús; Arnáiz, Eduardo; Díaz, Laura; Muñoz‐Fernández, María Ángeles; Gómez‐Sal, Pilar; Ottaviani, M. Francesca; Gómez, Rafael; Mata, F. Javier de la

doi:10.1002/ejic.201001121

Cited by 18 publications

(10 citation statements)

References 40 publications

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“…In our previous work, 31,32 we synthesized and characterized some sulfonate and carboxylate-containing N-donor ligands, and their corresponding metal (Ni, Co, Cu and Zn) complexes.…”

Section: Resultsmentioning

confidence: 99%

“…By using copper ions as spin probes, it was possible to characterize the dendrimer structure with respect to the distribution and fluidity of different interacting sites in the dendrimer interior and at the external surface. 10,18,[20][21][22][23][24][25] Following up our previous work 31,32 on the synthesis of metal mono-nuclear compounds with antiviral activity, and the dendrimer EPR characterization work by using copper complexation, 10,18,[20][21][22][23][24][25] we now report the synthesis and characterization of first, second and third generations of PPI dendrimers with an ethylenediamino (EDA) core. We selected a divergent procedure 33 for the synthesis of PPI dendrimers from the EDA core, which avoided the use of metal catalysts.…”

Section: Introductionmentioning

confidence: 99%

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Anionic sulfonated and carboxylated PPI dendrimers with the EDA core: synthesis and characterization of selective metal complexing agents

García‐Gallego¹,

Cangiotti²,

Fiorani³

et al. 2013

Dalton Trans.

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Herein we describe the synthesis and characterization of new sulfonated and carboxylated poly(propyleneimino) (PPI) dendrimers with the ethylenediamino (EDA) core, at generations 1, 2 and 3. By means of UV-Vis and EPR spectroscopy, using Cu(2+) as a probe, we concluded that these dendrimers show a specific pattern in the coordination of metal ions. In agreement with the UV-Vis studies, EPR spectra of carboxylated compounds are constituted by 3 different signals which appear and then disappear with increasing copper concentration, corresponding to the saturation of different copper complexation sites. At the lowest copper concentration up to a 1:1 molar ratio between Cu(II) and the dendrimer, the spectrum is characteristic of a CuN2O2 coordination at the core of the dendrimer. The spectrum appearing at higher Cu(II) concentrations indicates a peripheral location of the ions coordinating one nitrogen and 3 oxygen atoms in a square planar geometry in restricted mobility conditions. For the highest concentrations tested, copper ions are confined at the external dendrimer surface with CuO4 coordination. For sulfonate systems, the EPR results are in line with a weaker interaction of Cu(II) with the nitrogen sites and a stronger interaction with the oxygen (SO3(-)) groups with respect to the interactions measured by EPR for carboxylate systems.

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“…In our previous work, 31,32 we synthesized and characterized some sulfonate and carboxylate-containing N-donor ligands, and their corresponding metal (Ni, Co, Cu and Zn) complexes.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anionic sulfonated and carboxylated PPI dendrimers with the EDA core: synthesis and characterization of selective metal complexing agents

García‐Gallego¹,

Cangiotti²,

Fiorani³

et al. 2013

Dalton Trans.

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“…The parameters reported in Table were compared with other magnetic parameters reported in the literature for similar copper(II) complexes to identify the structure and coordination of the dendron complexes . All signals correspond to quite distorted square‐planar copper(II) coordination environments.…”

Section: Resultsmentioning

confidence: 99%

“…The parameters reportedi nT able 2w ere compared with other magnetic parameters reported in the literature for similar copper(II) complexes to identify the structure and coordination of the dendron complexes. [56,57,69,70] All signals correspond to quite distorted square-planar copper(II) coordination environments. Signal 1, which is well resolved for all samples with the exception of 6,i se asily ascribed to CuÀO4 coordinationw ith sulfonate groups at the dendron surface; water molecules occupy the other coordination sites.…”

Section: Synthesis Of Aunpsmentioning

confidence: 99%

Dendronized Anionic Gold Nanoparticles: Synthesis, Characterization, and Antiviral Activity

Peña-González

García-Broncano

Ottaviani

et al. 2016

Chemistry A European J

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Anionic carbosilane dendrons decorated with sulfonate functions and one thiol moiety at the focal point have been used to synthesize water-soluble gold nanoparticles (AuNPs) through the direct reaction of dendrons, gold precursor, and reducing agent in water, and also through a place-exchange reaction. These nanoparticles have been characterized by NMR spectroscopy, TEM, thermogravimetric analysis, X-ray photoelectron spectroscopy (XPS), UV/Vis spectroscopy, elemental analysis, and zeta-potential measurements. The interacting ability of the anionic sulfonate functions was investigated by EPR spectroscopy with copper(II) as a probe. Different structures and conformations of the AuNPs modulate the availability of sulfonate and thiol groups for complexation by copper(II). Toxicity assays of AuNPs showed that those produced through direct reaction were less toxic than those obtained by ligand exchange. Inhibition of HIV-1 infection was higher in the case of dendronized AuNPs than in dendrons.

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“…The M–N bond lengths fall in the expected ranges. Likewise, the sulfonate–metal bonds of 205.3 to 209.2 pm are at the lower end of typical chelating sulfonate bonds towards these metal centres; for example, these bonds are 210.3 pm in [Co(3‐mpSO 3 ) 2 (H 2 O) 2 ] (3‐mpSO 3 H = 3‐methylpyridine‐2‐sulfonic acid),28 207.2 and 210.3 pm in [Ni(phen)(H 2 O) 2 {CH 2 (SO 3 ) 2 }] (phen = 1,10‐phenanthroline)29 and 209.8 pm in [Zn{O 3 S(CH 2 ) 2 N(Me)(CH 2 ) 2 N(Me)(CH 2 ) 2 SO 3 }(H 2 O) 2 ] · 2H 2 O 30…”

Section: Resultsmentioning

confidence: 99%

Na₂(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes

Oelkers

2014

Eur J Inorg Chem

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The sulfonated bipyridine derivative disodium 6,6Ј-bis-(sulfonatomethyl)-2,2Ј-bipyridine [Na 2 (smbipy)] was synthesized, and its complexation behaviour towards divalent 3d metals in aqueous solution was explored. The complexes of late 3d metals [M(smbipy)(H 2 O) 2 ]·H 2 O (M = Co, Ni, Zn) and [Cu(smbipy)(H 2 O)] are sparingly soluble in water, and their crystal structures show fourfold equatorial coordination (κ 4 N,NЈ,O,OЈ) of the smbipy ligand. Ammonia-rich solutions of the Ni II and Cu II aqua complexes yield the decomplexation [a] 5838 products [Ni(NH 3 ) 6 ](smbipy), [Ni(NH 3 ) 5 (H 2 O)](smbipy) and [Cu(NH 3 ) 4 ](smbipy)·2H 2 O. Buffered solutions with a reduced ammonia content lead to [Ni(smbipy)(NH 3 ) 2 ] and [Cu(smbipy)(NH 3 ) 3 ]·2H 2 O, and the latter shows twofold coordination of the smbipy ligand through the nitrogen atoms only (κ 2 N,NЈ). When nearly quantitative amounts of ammonia are applied, two closely related complexes with the core motif [(smbipy)Cu(μ-OH) 2 Cu] form. Crystal structures of all complexes were obtained, and their features are discussed. Scheme 1. Examples of sulfonated ligands that do not show significant sulfonate binding towards metal centres.

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Transition‐Metal Complexes Based on a Sulfonate‐Containing N‐Donor Ligand and Their Use as HIV Antiviral Agents

Cited by 18 publications

References 40 publications

Anionic sulfonated and carboxylated PPI dendrimers with the EDA core: synthesis and characterization of selective metal complexing agents

Anionic sulfonated and carboxylated PPI dendrimers with the EDA core: synthesis and characterization of selective metal complexing agents

Dendronized Anionic Gold Nanoparticles: Synthesis, Characterization, and Antiviral Activity

Na₂(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes

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Transition‐Metal Complexes Based on a Sulfonate‐Containing N‐Donor Ligand and Their Use as HIV Antiviral Agents

Cited by 18 publications

References 40 publications

Anionic sulfonated and carboxylated PPI dendrimers with the EDA core: synthesis and characterization of selective metal complexing agents

Anionic sulfonated and carboxylated PPI dendrimers with the EDA core: synthesis and characterization of selective metal complexing agents

Dendronized Anionic Gold Nanoparticles: Synthesis, Characterization, and Antiviral Activity

Na2(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes

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Product

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Na₂(smbipy) – A Bipyridine‐Derived Ligand with Chelating Sulfonate Tags and Its 3d Metal Complexes