Triphenylarsonium-functionalised gold nanoparticles: potential nanocarriers for intracellular therapeutics

Lalwani, Nikhil; Chen, Yu-Su; Brooke, Gemma; Cross, Neil; Allen, David W.; Reynolds, Alan; Ojeda, Jesús J.; Tizzard, Graham J.; Coles, Simon J.; Bricklebank, Neil

doi:10.1039/c4cc09304f

Cited by 8 publications

(3 citation statements)

References 30 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%

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%

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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“…After internalization, it is necessary to direct NPs to their specific target within cells. Conjugation of cationic groups to the surface of AuNPs results in water‐dispersed NPs . Triphenylphosphonium (TPP) is a lipophilic phosphonium cation with a high affinity to mitochondria.…”

Section: Resultsmentioning

confidence: 99%

Nanoscale Optoregulation of Neural Stem Cell Differentiation by Intracellular Alteration of Redox Balance

Hassanpour-Tamrin

Taheri

Hasani-Sadrabadi

et al. 2017

Adv Funct Materials

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Regulation of stem cell (SC) fate, a decision between self-renewal and differentiation, is of immense importance in regenerative medicine and has been proven to be a powerful stimulus regulating many cell functions influencing the SC fate. This study uses triphenylphosphonium-functionalized gold nanoparticles (TPP-AuNPs) to explore the interplay of intracellular electromagnetic (EM) exposure and the SC fate. Localized EM waves are generated inside neural stem cells (NSCs) to stimulate TPP-AuNPs (AuNPs), targeting the mitochondria through inducing reactive oxygen species and differentiating these cells into neurons. Following laser irradiation of TPP-AuNPs-transfected NSCs, their differentiation to neurons is monitored by tracing the relevant markers both at the genetic and protein levels. The electrophysiology technique is further used to examine the functionality of neurons. The results confirm that TPP-AuNPs subjected to electromotive forces have the potential to regulate cellular fate, although further investigations are still required to shed light on the mechanisms underlying the interaction of EM-stimulated TPP-AuNPs on cellular fate to design highly adjustable cell differentiation and reprogramming methods.

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“…When compared to cisplatin, it showed greater activity in breast, leukemia, colon, and central nervous system cancer cell lines (Miodragović et al 2019 ). Other systems have been investigated for the effective delivery of arsonium compounds in cancer therapeutics, such as the triphenylarsonium-functionalised gold nanoparticles (Lalwani et al 2015 ). The gold nanoparticles are decorated with the triphenylarsonium groups to serve as potential nanocariers for intracellular therapeutics.…”

Section: Inorganic and Organic Arsenic-containing Drugsmentioning

confidence: 99%

Arsenic in medicine: past, present and future

et al. 2022

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Arsenicals are one of the oldest treatments for a variety of human disorders. Although infamous for its toxicity, arsenic is paradoxically a therapeutic agent that has been used since ancient times for the treatment of multiple diseases. The use of most arsenic-based drugs was abandoned with the discovery of antibiotics in the 1940s, but a few remained in use such as those for the treatment of trypanosomiasis. In the 1970s, arsenic trioxide, the active ingredient in a traditional Chinese medicine, was shown to produce dramatic remission of acute promyelocytic leukemia similar to the effect of all- trans retinoic acid. Since then, there has been a renewed interest in the clinical use of arsenicals. Here the ancient and modern medicinal uses of inorganic and organic arsenicals are reviewed. Included are antimicrobial, antiviral, antiparasitic and anticancer applications. In the face of increasing antibiotic resistance and the emergence of deadly pathogens such as the severe acute respiratory syndrome coronavirus 2, we propose revisiting arsenicals with proven efficacy to combat emerging pathogens. Current advances in science and technology can be employed to design newer arsenical drugs with high therapeutic index. These novel arsenicals can be used in combination with existing drugs or serve as valuable alternatives in the fight against cancer and emerging pathogens. The discovery of the pentavalent arsenic-containing antibiotic arsinothricin, which is effective against multidrug-resistant pathogens, illustrates the future potential of this new class of organoarsenical antibiotics.

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Triphenylarsonium-functionalised gold nanoparticles: potential nanocarriers for intracellular therapeutics

Cited by 8 publications

References 30 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

Nanoscale Optoregulation of Neural Stem Cell Differentiation by Intracellular Alteration of Redox Balance

Arsenic in medicine: past, present and future

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