Water-soluble gold nanoparticles stabilized with cationic phosphonium thiolate ligands

Ju‐Nam, Yon; Chen, Yu-Su; Ojeda, Jesús J.; Allen, David W.; Cross, Neil; Gardiner, Philip H. E.; Bricklebank, Neil

doi:10.1039/c2ra21421k

Cited by 19 publications

(14 citation statements)

References 71 publications

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“…Our own work has focused on the synthesis and biological properties of alkylthiosulfate zwitterions [3][4][5][6], and alkylthioacetate salts [3,7], conjugated with triphenylphosphine and other trialkyl-and triaryl-phosphines [3][4][5][6][7], and also arsines [8], which can be used as precursors for the formation of phosphonium-or arsoniumfunctionalized gold nanoparticles [4,8], potentially useful species in mitochondriatargeted pharmaceutical nanotechnology. Other groups have developed and applied our methodology [9,10].…”

Section: Introductionmentioning

confidence: 99%

“…Other groups have developed and applied our methodology [9,10]. Although triphenylphosphonium-functionalized nanoparticles are soluble in water and biological media [4,10] and are taken-up by cells [4,9] the parent triphenylphosphonioalkylthiosulfate zwitterions are insoluble in aqueous media [3,10]. This observation has prompted us to investigate alternative triarylphosphonium groups in an attempt to improve the aqueous solubility of the zwitterions.…”

Section: Introductionmentioning

confidence: 99%

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Methoxy-phenyl groups reduce the cytotoxicity and increase the aqueous solubility of phosphonium zwitterions and salts

Lalwani

Allen

Coles³

et al. 2019

Polyhedron

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The ability of phosphonium cations to act as intracellular transport vectors is wellestablished. Previous research has demonstrated that phosphonioalkylthiosulfate zwitterions, and -thioacetylalkylphosphonium salts are useful precursors for the formation of phosphonium-functionalised gold nanoparticles and enable the nanoparticles to be transported into cells for diagnostic and therapeutic purposes. In this report we describe the synthesis and characterisation of a series of phosphonioalkylthiosulfate zwitterions, and-thioacetylalkylphosphonium salts derived from the methoxy-phenylphosphines tris(2,4,6-trimethoxyphenyl)phosphine, tris(2,6-dimethoxyphenyl)phosphine and tri(4-methoxyphenyl)phosphine. The methoxyphenyl-substituted phosphonium compounds show greater solubility in aqueous systems than the corresponding phenyl derivatives and cytotoxicity studies reveal that the compounds are significantly less toxic than the related triphenylphosphonium derivatives. The solid-state structures of the tris(2,4,6-trimethoxyphenyl)-and tris(2,6dimethoxyphenyl)-phosphoniopropylthiosulfate zwitterions have been investigated by single crystal X-ray crystallography. The differences in the molecular packing of the compounds may account for greater solubility of these zwitterions in aqueous solutions.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Methoxy-phenyl groups reduce the cytotoxicity and increase the aqueous solubility of phosphonium zwitterions and salts

Lalwani

Allen

Coles³

et al. 2019

Polyhedron

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“…This can be due to the differing passivation kinetics of the types of ligands used for this study, and the cleavage of the sulfur-sulfur and sulfur-carbon bonds in the thiosulfate and thioacetate species. 45 The mechanisms of these cleavages are still unclear.…”

Section: (C) Uv-visible and Tem Studiesmentioning

confidence: 99%

“…The presence of reducing agent in the solution also influences the cleavage of sulfur-sulfur and sulfur-carbon bonds. 45 In the case of the tri(p-tolyl)phosphoniopropylthiolate functionalised gold nanoparticles, they could only be produced using the DMSO method. The corresponding UV-Visible spectrum showed that the SPB is centred at 529 nm (Figure 4).…”

Section: (C) Uv-visible and Tem Studiesmentioning

confidence: 99%

Highly stable noble metal nanoparticles dispersible in biocompatible solvents: synthesis of cationic phosphonium gold nanoparticles in water and DMSO

2016

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In this work, we report the synthesis of novel cationic phosphonium gold nanoparticles dispersible in water and dimethyl sulfoxide (DMSO) for their potential use in biomedical applications. All the cationic-functionalising ligands currently reported in the literature are ammonium-based species. Here, the synthesis and characterisation of an alternative system, based on phosphonioalkylthiosulfate zwitterions and phosphonioalkylthioacetate were carried out. We have also demonstrated that our phosphonioalkylthiosulfate zwitterions readily disproportionate into phosphonioalkylthiolates in situ during the synthesis of gold nanoparticles produced by the borohydride reduction of gold(III) salts. The synthesis of the cationic gold nanoparticles using these phosphonium ligands was carried out in water and DMSO. UV-visible spectroscopic and TEM studies have shown that the phosphonioalkylthiolates bind to the surface of gold nanoparticles which are typically around 10 nm in diameter. The resulting cationic-functionalised gold nanoparticles are dispersible in aqueous media and in DMSO, which is the only organic solvent approved by the U.S. Food and Drug Administration (FDA) for drug carrier tests. This indicates their potential future use in biological applications. This work shows the synthesis of a new family of phosphonium-based ligands, which behave as cationic masked thiolate ligands in the functionalisation of gold nanoparticles. These highly stable colloidal cationic phosphonium gold nanoparticles dispersed in water and DMSO can offer a great opportunity for the design of novel biorecognition and drug delivery systems.

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“…9 Phosphonium species have been found to be extremely valuable for mitochondria-targeted therapeutics and diagnostics. We have prepared phosphoniumfunctionalised gold nanoparticles [14][15][16] which are accumulated by cells and shown by TEM to be localised in the mitochondria. 7 Recent work has demonstrated the potential of combining phosphonium compounds with nanotechnological approaches to traffic pharmaceutical and diagnostic moieties into mitochondria.…”

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Triphenylarsonium-functionalised gold nanoparticles: potential nanocarriers for intracellular therapeutics

et al. 2015

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Water-soluble gold nanoparticles stabilized with cationic phosphonium thiolate ligands

Cited by 19 publications

References 71 publications

Methoxy-phenyl groups reduce the cytotoxicity and increase the aqueous solubility of phosphonium zwitterions and salts

Methoxy-phenyl groups reduce the cytotoxicity and increase the aqueous solubility of phosphonium zwitterions and salts

Highly stable noble metal nanoparticles dispersible in biocompatible solvents: synthesis of cationic phosphonium gold nanoparticles in water and DMSO

Triphenylarsonium-functionalised gold nanoparticles: potential nanocarriers for intracellular therapeutics

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