Preparation and Structural Characterization of a Platinum Catecholate Complex Containing Two 3-Ethynylthiophene Groups

Kinder, James D.; Youngs, Wiley J.

doi:10.1021/om950155t

Cited by 23 publications

(18 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We need to point out that a [Pt(PPh 3 ) 2 ] 2+ catecholate complex was reported by Kinder and Youngs in 1996, but up to now no examples have been described of complexes formed by catecholate with cis ‐DAP. The molecular structure of the [Pt(PPh 3 ) 2 ] 2+ catecholate complex, as determined by X‐ray crystallography, showed the metal ion in a square‐planar environment, with the coordination sphere occupied by two monodentate phosphorus ligands and a bidentate catecholate species in cis configuration.…”

Section: Resultsmentioning

confidence: 95%

Tandem mass spectrometry characterization of a conjugate between oleuropein and hydrated cis‐diammineplatinum(II)

Ventura

Abbattista

Calvano

et al. 2019

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Rationale Oleuropein (Ole) has been claimed to mitigate cisplatin (CP)‐induced acute injury in kidney and liver of mice. In vitro reactivity of hydrated CP species with Ole, and an Ole metabolite, hydroxytyrosol (HT), is of great interest as the preliminary step for gathering in vivo information on the possible physiological role of the Ole/HT‐cis‐diammineplatinum(II) (Ole/HT‐cis‐DAP) conjugate. Methods Reversed‐phase liquid chromatography coupled to electrospray ionization mass spectrometry using a linear ion trap instrument (RPLC/ESI‐MS) and tandem mass (MS/MS) measurements, both in positive and negative ion mode, revealed the molecular identity of platinum‐based conjugates. Results The Ole‐cis‐DAP conjugate (i.e., C25H36N2O13PtII) features two cis‐ammine non‐leaving ligands and a bidentate catechol ligand moiety belonging to Ole; the coordination of the central Pt(II) is square‐planar with non‐equivalent bond angles compared with the ideal arrangement of 90°. HT, the free Ole metabolite excreted in human urine, acts as bidentate O,O‐donor ligand of cis‐DAP as well. Conclusions The first evidence, together with structural information, is provided about the in vitro formation of a conjugate between cis‐DAP and Ole or its urinary metabolite HT. Presuming that such conjugates are also generated in vivo, the mechanisms by which they might contribute to reduce CP toxicity remain to be elucidated.

show abstract

Section: Resultsmentioning

confidence: 95%

Tandem mass spectrometry characterization of a conjugate between oleuropein and hydrated cis‐diammineplatinum(II)

Ventura

Abbattista

Calvano

et al. 2019

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…An intense band occurs in the IR spectra at about 1200-1300 cm -1 which is typical of C-O stretching modes in catecholato-metal structures. [24,31] In the case of the unsymmetrical ligand 1 diastereomeric complexes form which we were unable to separate. These diastereomers are likely to show slightly different optical properties, which are not considered in the following text.…”

Section: Synthesis and Characterisationmentioning

confidence: 83%

“…All reagents were purchased from commercial sources and used as received. Methyl 3-(3,4-dihydroxy)phenyl-2-propenoate (1), [35] 1,2-bis(tert-butyldimethylsilyloxy)-4,5-diiodobenzene (5), [31] 1-ethynyl-4-nitrobenzene (6), [36] and (4-ethynylphenyl)dimethylamine (11) [36] were prepared according to literature procedures.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Linear Optical Properties of Tris(catecholato)metal(III,IV) Complexes with Acceptor‐Substituted Ligands

Kriegisch

Lambert

2005

Eur J Inorg Chem

View full text Add to dashboard Cite

show abstract

“…All reagents and 4 were purchased from commercial sources and used as received. Compounds 1, [17] 2, [18] 3, [18] pCat-di-PENO 2 and pCat-di-PENMe 2 [19] were prepared according to literature procedures.…”

Section: Discussionmentioning

confidence: 99%

A Rational Design of Catechol‐Based Compounds: An Experimental and Theoretical Study of Optical Properties

Aronica

Venancio‐Marques

Chauvin

et al. 2009

Chemistry A European J

View full text Add to dashboard Cite

The synthesis and optical properties of 4,5-disubstituted (tert-butyldimethylsilyloxy)-protected catechol derivatives are reported. One or two carbon-carbon triple bond functions were introduced through the Sonogashira cross-coupling reaction. The effects on the optical properties of monosubstitution at the 4-position or disubstitution at the 4- and 5-positions of these catechol derivatives with electron-withdrawing or -donating substituents have been investigated. The experimental chemical-structure-polarisability relationship has been studied by using the Lippert-Mataga correlation and compared with the results of a theoretical study carried out with DFT calculations. These compounds are promising candidates for the fine-tuning of internal charge transfer, but also as potential non-linear chromophores and ligands within multifunctional coordination complexes.

show abstract

Preparation and Structural Characterization of a Platinum Catecholate Complex Containing Two 3-Ethynylthiophene Groups

Abstract: The reaction of 1,2-bis(tert-butyldimethylsiloxy)-3,4-bis(3-ethynylthiophene-yl)benzene (4) with Pt(P(Ph)3)2Cl2 and tetrabutylammonium fluoride produces a novel platinum catecholate complex.

Cited by 23 publications

References 24 publications

Tandem mass spectrometry characterization of a conjugate between oleuropein and hydrated cis‐diammineplatinum(II)

Tandem mass spectrometry characterization of a conjugate between oleuropein and hydrated cis‐diammineplatinum(II)

Synthesis and Linear Optical Properties of Tris(catecholato)metal(III,IV) Complexes with Acceptor‐Substituted Ligands

A Rational Design of Catechol‐Based Compounds: An Experimental and Theoretical Study of Optical Properties

Contact Info

Product

Resources

About