The synthesis and characterisation of masked phosphonioalkyl selenoates: Potential ligands for the production of functionalised gold nanoparticles

Ju‐Nam, Yon; Allen, David W.; Gardiner, Philip H. E.; Light, Mark E.; Hursthouse, Michael B.; Bricklebank, Neil

doi:10.1016/j.jorganchem.2007.07.038

Cited by 11 publications

(3 citation statements)

References 28 publications

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“…The thioacetylalkylphosphonium salts therefore behave in the same way as our earlier reported phosphonioalkylthiosulfate zwitterions under reductive conditions [7,8].…”

Section: Ligand Synthesissupporting

confidence: 78%

“…Masked thiolates are easier to handle and less prone to oxidation than conventional thiol ligands. In related studies, we have also recently reported the synthesis of two new masked phosphonioalkylselenolate ligands 2 and explored their ability to stabilise gold nanoparticles [8]. The attachment of charged or hydrophilic groups to the surface of nanoparticles is an attractive proposition for improving the aqueous solubility of the resulting MPCs and facilitating biomolecular recognition through non-covalent interactions [5].…”

Section: Introductionmentioning

confidence: 99%

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ω-Thioacetylalkylphosphonium salts: Precursors for the preparation of phosphonium-functionalised gold nanoparticles

Ju‐Nam

Allen

Gardiner

et al. 2008

Journal of Organometallic Chemistry

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“…The thioacetylalkylphosphonium salts therefore behave in the same way as our earlier reported phosphonioalkylthiosulfate zwitterions under reductive conditions [7,8].…”

Section: Ligand Synthesissupporting

confidence: 78%

Section: Introductionmentioning

confidence: 99%

ω-Thioacetylalkylphosphonium salts: Precursors for the preparation of phosphonium-functionalised gold nanoparticles

Ju‐Nam

Allen

Gardiner

et al. 2008

Journal of Organometallic Chemistry

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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%

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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Organic Selenocyanates, Tellurocyanates and Related Compounds

Toshimitsu¹

2013

Patai's Chemistry of Functional Groups

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Preparations, physical properties and reactions of organic selenocyanates, isoselenocyanates, and tellurocyanates are described. The preparations of organic selenocyanates include synthetic procedures (1) by substitution of halogen and related group, (2) from diazonium salts, (3) from organometallic compounds, (4) by selenocyanation, and (5) by formation of an SeCN bond. The preparations of organic isoselenocyanates include synthetic procedures (1) by formation of a CSe bond, (2) by substitution of halogen atom and (3) by [3.3]sigmatropic rearrangement. The reactions of organic selenocyanates include (1) additions to the CN bond, (2) substitution of the CN group, (3) elimination of the CN group, and (4) isomerization to isoselenocyanates. The reactions of organic isoselenocyanates include (1) addition of nitrogen nucleophile, (2) addition of oxygen nucleophile, (3) addition of sulfur, selenium or tellurium nucleophile, and (4) reaction of carbon nucleophile. Coverage of the literature is nearly complete from 1986 to 2011.

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The synthesis and characterisation of masked phosphonioalkyl selenoates: Potential ligands for the production of functionalised gold nanoparticles

Cited by 11 publications

References 28 publications

ω-Thioacetylalkylphosphonium salts: Precursors for the preparation of phosphonium-functionalised gold nanoparticles

ω-Thioacetylalkylphosphonium salts: Precursors for the preparation of phosphonium-functionalised gold nanoparticles

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

Organic Selenocyanates, Tellurocyanates and Related Compounds

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