<i>S</i>-[4-(Trimethylammonio)phenyl]thiosulfate, an aromatic organic thiosulfate

Chen, Jin Xiang; Xu, Qian; Zhang, Yong; Zain, Sharifuddin M.; Ng, Seik Weng; Lang, Jihui

doi:10.1107/s010827010401443x

Cited by 4 publications

(6 citation statements)

References 16 publications

(9 reference statements)

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“…Over the last few decades, disulfides have stimulated intense interest owing to their donor capabilities towards metal ions (Bernal et al, 1976;Haller & Treichel, 1983;Roesky et al, 1984;Kitaura et al, 2002) and their potential application in biological systems (Hald et al, 1948;Ricci & Bernal, 1969). However, structural information for aromatic disulfides is limited (Woodard et al, 1976;Cannon et al, 2000;Anacona et al, 2003;Nicholson et al, 2006;Clegg & Coxall, 2005), especially as far as aromatic disulfides containing an ammonium (-NR 3 ) group (Chen, Xu, Zhang, Zain et al, 2004) are concerned.…”

Section: Commentmentioning

confidence: 99%

Bis[4-(trimethylammonio)phenyl] disulfide diiodide acetone solvate

et al. 2009

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The title compound, C(18)H(26)N(2)S(2)(2+).2I(-).2C(3)H(6)O, is an intermediate in the design of the zwitterionic thiolate 4-(trimethylammonio)benzenethiolate (Tab), in which a pair of aryl-substituted S atoms are linked by a covalent bond. The central S-S bond length is 2.020 (3) A and the C(ar)-S-S-C(ar) torsion angle is -84.1 (2) degrees . The crystal structure is stabilized by nonclassical hydrogen bonds which occur as intramolecular C-H...I interactions and intermolecular C-H...S and C-H...O contacts. In the crystal structure, both the dication and the two symmetrically independent iodide counter-anions are located on twofold crystallographic axes, whereas the acetone solvent molecule occupies a general position.

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Section: Commentmentioning

confidence: 99%

Bis[4-(trimethylammonio)phenyl] disulfide diiodide acetone solvate

et al. 2009

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“…Perhaps surprisingly, the structures of few organic thiosulfate zwitterions have been reported. 18 Both compounds display the expected tetrahedral geometry around the arsenic atoms with mean C-As-C bond angles of 109.5(2)1 in 3 and 109.46(11)1 in 4. In zwitterion 3 (Fig.…”

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confidence: 95%

“…18 Both compounds display the expected tetrahedral geometry around the arsenic atoms with mean C-As-C bond angles of 109.5(2)1 in 3 and 109.46(11)1 in 4. † The structures of 3 and 4 were confirmed by X-ray crystallography.…”

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“…† The structures of 3 and 4 were confirmed by X-ray crystallography. 18 The S-S bond length [2.1081(18) Å], is slightly shorter than that of the corresponding phosphonium compound [2.1117(9) Å], 15 but longer than the S-S bond in ionic thiosulfate ions such as Me 2 HN(CH 2 S 2 O 3 ) 2 À Na + . 18 Both compounds display the expected tetrahedral geometry around the arsenic atoms with mean C-As-C bond angles of 109.5(2)1 in 3 and 109.46(11)1 in 4.…”

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“…Perhaps surprisingly, the structures of few organic thiosulfate zwitterions have been reported. 18 Within the crystal lattice the zwitterions pack fairly loosely, held together by hydrogen-bonding interactions between the sulfate oxygens and the phenyl hydrogens, but there is no close interaction between the arsonium and the thiosulfate moieties. In zwitterion 3 (Fig.…”

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Triphenylarsonium-functionalised gold nanoparticles: potential nanocarriers for intracellular therapeutics

et al. 2015

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Biological and structural studies of phosphonium ‘masked thiolate’ compounds

Chen

Allen

Tizzard³

et al. 2017

European Journal of Medicinal Chemistry

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The ability of phosphonium cations to act as intracellular transport vectors is well-established. Phosphonioalkylthiosulfate zwitterions, and ω-thioacetylalkylphosphonium salts, which act as 'masked thiolate' ligands, are useful precursors for the formation of phosphonium-functionalised gold nanoparticles, enabling the nanoparticles to be transported into cells for diagnostic and therapeutic purposes. In this study we have completed cytotoxicity studies of ω-thioacetylpropylphosphonium salts derived from triphenylphosphine and tri(4-fluorophenyl)phosphine, which show that the compounds are only toxic towards PC3 prostate cancer cells at high concentrations and at prolonged incubation periods and display IC values of 67 μM and 252 μM respectively, significantly higher than those of other phosphonium salts. MALDI-TOF-MS has been used to investigate the uptake of the compounds by PC3 cells and to quantify detectable levels of the compounds inside the cells. The structures of ω-thioacetylpropyl(tri-4-fluorophenyl) phosphonium bromide and the corresponding tri(4-fluorophenyl)phosphoniopropylthiosulfate zwitterion have been investigated by single crystal X-ray crystallography. The results show that molecules of the zwitterion are held together through an extensive array of electrostatic and non-covalent interactions. The unit cell of ω-thioacetylpropyl(tri-4-fluorophenyl)phosphonium bromide contains eight cations together with eight bromide anions and two waters of crystallisation, all held together through a complex network of hydrogen bonds. The differences in the molecular packing of the two compounds may account for the lower solubility of the zwitterion in aqueous solutions, compared with that of the phosphonium salt.

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S-[4-(Trimethylammonio)phenyl]thiosulfate, an aromatic organic thiosulfate

Cited by 4 publications

References 16 publications

Bis[4-(trimethylammonio)phenyl] disulfide diiodide acetone solvate

Bis[4-(trimethylammonio)phenyl] disulfide diiodide acetone solvate

Triphenylarsonium-functionalised gold nanoparticles: potential nanocarriers for intracellular therapeutics

Biological and structural studies of phosphonium ‘masked thiolate’ compounds

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