Studies Toward an Ideal Fluorescence Method to Measure Palladium in Functionalized Organic Molecules: Effects of Sodium Borohydride, Temperature, Phosphine Ligand, and Phosphate Ions on Kinetics

Song, Fengling; Carder, Evan; Kohler, Clare; Koide, Kazunori

doi:10.1002/chem.201001316

Cited by 51 publications

(33 citation statements)

References 55 publications

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“…The reaction of deallylation using the electron-poor phosphine ligand (TFP; tri-2-furylphosphine) to better generate the coordinatively unsaturated Pd(0) species has indeed been known1617 (see Supplementary Fig. 1c for scheme), but here we discover its utility in physiological conditions.…”

Section: Resultsmentioning

confidence: 76%

Nano-palladium is a cellular catalyst for in vivo chemistry

et al. 2017

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Palladium catalysts have been widely adopted for organic synthesis and diverse industrial applications given their efficacy and safety, yet their biological in vivo use has been limited to date. Here we show that nanoencapsulated palladium is an effective means to target and treat disease through in vivo catalysis. Palladium nanoparticles (Pd-NPs) were created by screening different Pd compounds and then encapsulating bis[tri(2-furyl)phosphine]palladium(II) dichloride in a biocompatible poly(lactic-co-glycolic acid)-b-polyethyleneglycol platform. Using mouse models of cancer, the NPs efficiently accumulated in tumours, where the Pd-NP activated different model prodrugs. Longitudinal studies confirmed that prodrug activation by Pd-NP inhibits tumour growth, extends survival in tumour-bearing mice and mitigates toxicity compared to standard doxorubicin formulations. Thus, here we demonstrate safe and efficacious in vivo catalytic activity of a Pd compound in mammals.

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Section: Resultsmentioning

confidence: 76%

Nano-palladium is a cellular catalyst for in vivo chemistry

et al. 2017

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“…34 Improvements to this detection methodology include the introduction of reducing agents and phosphine ligands in order to increase the catalytic activity of the palladium, which in turn leads to increased sensitivity of the assay. [35][36] Furthermore, a bis-allyl ether derivative of 1 has been very recently reported that can significantly reduce background fluorescence and as such, delivers a >300-fold signal increase within a 5 minute reaction period. 37 Alternative moieties have also been shown to be selective for palladium detection as a propargyl derivative of compound 1 has been shown to be able to monitor palladium accumulation in living systems via fluorescence.…”

Section: Target Catalysismentioning

confidence: 99%

Approaches towards molecular amplification for sensing

Goggins

Frost

2016

Analyst

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Diagnostic assays that rely on molecular interactions have come a long way; from initial reversible detection systems towards irreversible reaction indicator-based methods. More recently, the emergence of innovative molecular amplification methodologies has revolutionised sensing, allowing diagnostic assays to achieve ultra-low limits of detection. There have been a significant number of molecular amplification approaches developed over recent years to accommodate the wide variety of analytes that require sensitive detection. To celebrate this achievement, this comprehensive critical review has been compiled to give a broad overview of the many different approaches used to attain amplification in sensing with an aim to inspire the next generation of diagnostic assays looking to achieve the ultimate detection limit. This review has been created with the focus on how each conceptually unique molecular amplification methodology achieves amplification, not just its sensitivity, while highlighting any key processes. Excluded are any references that were not found to contain an obvious molecular amplifier or amplification component, or that did not use an appropriate signal readout that could be incorporated into a sensing application. Additionally, methodologies where amplification is achieved through advances in instrumentation are also excluded. Depending upon the type of approach employed, amplification strategies are divided into four categories: target, label, signal or receptor amplification. More recent, more complex protocols combine a number of approaches and are therefore categorised by which amplification component described within was considered as the biggest advancement. The advantages and disadvantages of each methodology are discussed along with any limits of detection, if stated in the original article. Any subsequent use of the methodology within sensing or any other application is also mentioned to draw attention to its practicality. The importance of amplification within sensing is wholly emphasised while perspectives on the future direction of the field are also shared.

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“…The other possibility is that a phosphate ion can act as a ligand for palladium(0). [26] Conclusions An efficient process has been developed for the carbonylation of chloroacetates to afford malonates by using [PdCl 2 (PPh 3 ) 2 ] as a catalyst with the aid of Bu 4 NI in a weakly alkaline buffer. Excellent selectivity (96 %) and yield (93 %) of DEM were obtained if the reaction was performed in anisole with Na 2 HPO 4 as a proton scavenger and Pd black was not generated.…”

Section: Discussionmentioning

confidence: 99%

Palladium‐Catalyzed Carbonylation of Chloroacetates to Afford Malonates: Controlling the Selectivity of the Product in a Buffer

Zhang

Guan

et al. 2012

ChemCatChem

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We report an efficient process for the synthesis of diethyl malonate (DEM) and other malonates through the palladium‐catalyzed carbonylation of chloroacetates. Excellent selectivity (96 %) and yield (94 %) were obtained without the formation of Pd black. For the first time, a weakly alkaline buffer was used to control the selectivity for DEM in the reaction and we discuss the relationship between the buffer medium and selectivity in the reaction. The combination of anisole as the solvent and a Na2HPO4/NaH2PO4 buffer was beneficial for completely restraining the phase‐transfer‐catalyzed substitution of DEM with ethyl chloroacetate, as well as accommodating the proposed [(PPh3)2PdI]−[Bu4N]+ intermediate, by providing a suitable environment for its stable existence. We achieved the highest efficiency in the catalytic cycle by fine‐tuning the balance between the rates of oxidative addition and reductive elimination; moreover, we synthesized a recoverable heterogeneous polymer‐bound Pd catalyst in 85 % yield that could be reused without an appreciable loss in activity over four cycles.

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Studies Toward an Ideal Fluorescence Method to Measure Palladium in Functionalized Organic Molecules: Effects of Sodium Borohydride, Temperature, Phosphine Ligand, and Phosphate Ions on Kinetics

Cited by 51 publications

References 55 publications

Nano-palladium is a cellular catalyst for in vivo chemistry

Nano-palladium is a cellular catalyst for in vivo chemistry

Approaches towards molecular amplification for sensing

Palladium‐Catalyzed Carbonylation of Chloroacetates to Afford Malonates: Controlling the Selectivity of the Product in a Buffer

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