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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
Methoxy-phenyl groups reduce the cytotoxicity and increase the aqueous solubility of phosphonium zwitterions and salts
The ability of phosphonium cations to act as intracellular transport vectors is well-established. Previous research has demonstrated that phosphonioalkylthiosulfate zwitterions, and ω-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 ω-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(2,6-dimethoxyphenyl)-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.
0277-5387
Lalwani, Nikhil
8362331f-dcf4-412f-a1f3-878af8e718e7
Allen, David W.
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Horton, Peter
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cross, Neil A.
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Bricklebank, Neil
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Lalwani, Nikhil
8362331f-dcf4-412f-a1f3-878af8e718e7
Allen, David W.
4cbcd21b-4bb9-40e8-baa9-27b1b3e5a7b2
Horton, Peter
154c8930-bfc3-495b-ad4a-8a278d5da3a5
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Cross, Neil A.
71a10a02-6a23-444a-85b5-6033d0ed4e0a
Bricklebank, Neil
6e082c98-a747-4690-bb37-f05f24d621f5

Lalwani, Nikhil, Allen, David W., Horton, Peter, Coles, Simon J., Cross, Neil A. and Bricklebank, Neil (2018) Methoxy-phenyl groups reduce the cytotoxicity and increase the aqueous solubility of phosphonium zwitterions and salts. Polyhedron. (doi:10.1016/j.poly.2018.10.069).

Record type: Article

Abstract

The ability of phosphonium cations to act as intracellular transport vectors is well-established. Previous research has demonstrated that phosphonioalkylthiosulfate zwitterions, and ω-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 ω-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(2,6-dimethoxyphenyl)-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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Accepted/In Press date: 27 October 2018
e-pub ahead of print date: 2 November 2018

Identifiers

Local EPrints ID: 426119
URI: http://eprints.soton.ac.uk/id/eprint/426119
ISSN: 0277-5387
PURE UUID: e77d869b-ae5d-403d-9cda-d026d171e2db
ORCID for Peter Horton: ORCID iD orcid.org/0000-0001-8886-2016
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 14 Nov 2018 17:30
Last modified: 26 Nov 2021 06:10

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Contributors

Author: Nikhil Lalwani
Author: David W. Allen
Author: Peter Horton ORCID iD
Author: Simon J. Coles ORCID iD
Author: Neil A. Cross
Author: Neil Bricklebank

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