Synthesis and antiviral activity of phosphonium salts

Романов, Г. В.; Поздеев, О. К.; Gil'manova, G. Kh.; Ryzhikova, T. Ya.; Semkina, E. P.

doi:10.1007/bf00765789

Cited by 6 publications

(2 citation statements)

References 14 publications

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“…31 Iodide 10 has previously been screened against influenza type A. 32 In contrast, screened ammonium compounds 11 – 17 , possessing a short heteroatom N + CH 2 SMe chain, showed IC 50 values greater than 500 μ m in experiments performed after either 24 or 48 h incubation, a concentration which is characteristic for compounds of rather low toxicity.…”

Section: Resultsmentioning

confidence: 99%

High Cytotoxic Activity of Phosphonium Salts and Their Complementary Selectivity towards HeLa and K562 Cancer Cells: Identification of Tri‐n‐butyl‐n‐hexadecylphosphonium bromide as a Highly Potent Anti‐HeLa Phosphonium Salt

Bachowska¹,

Kaźmierczak-Barańska²,

Cieślak³

et al. 2012

ChemistryOpen

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Quaternary ammonium and phosphonium salts have been screened for their toxic effect on HeLa and K562 cancer cell lines, as well as on normal HUVEC cells. Tri-n-butyl-n-hexadecylphosphonium bromide, the first phosphonium salt with a halogen anion tested against HeLa cells, was 12 times more potent (IC50 <5 μm after 24 and 48 h) than the clinically used reference compound cisplatin and 17 times more potent than tri-n-hexyltetradecylphosphonium bis(trifluoromethylsulfonyl)imide, which, to the best of our knowledge, is the first phosphonium salt to be evaluated in HeLa cells. However, it was inactive against K562 cells (24 and 48 h). According to a caspase-3/7 assay, its toxicity has not been connected with the induction of apoptosis. In contrast, triphenylalkylphosphonium iodides with shorter C1–5 alkyl chains were inactive against HeLa cells but very active against K562 cells (IC50=6–10 μm after 48 h). Phosphonium cations with halide counterions proved to be more potent than those with (CF3SO2)2N− as the anion, as in the anticancer agent NSC 747251, or other anions in molecules with similar alkyl chain lengths. On the other hand, a series of ammonium salts containing a short methylthiomethyl or methoxymethyl side chain revealed low cytotoxicity (IC50 >500 μm after 24 and 48 h) against both HeLa and K562 cancer cell lines as well as normal HUVEC cells, showing that the nontoxic N+CH2YMe (Y=S, O) structural motif in ammonium salts could be suitable for further optimization and development, especially in transfection experiments.

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Section: Resultsmentioning

confidence: 99%

High Cytotoxic Activity of Phosphonium Salts and Their Complementary Selectivity towards HeLa and K562 Cancer Cells: Identification of Tri‐n‐butyl‐n‐hexadecylphosphonium bromide as a Highly Potent Anti‐HeLa Phosphonium Salt

Bachowska¹,

Kaźmierczak-Barańska²,

Cieślak³

et al. 2012

ChemistryOpen

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“…Romanov et al synthesized a series of QPS with different alkyl or aryl substitutes, and studied their ability to suppress the proliferation of the inuenza A virus (H3N2). 15 All of the investigated QPS compounds exhibited antiviral activity, and the activity exceeded the antiviral action of rimantadine, a drug prescribed for the prevention and treatment of the inuenza A virus. By comparison, the two compounds propyltriphenyl-phosphonium bromide and butyltriphenyl-phosphonium bromide possess the highest chemotherapeutic index (CI 80 645), of which the toxicity for the chorion allantoid membrane was 250 ppm and the virucidal concentration for one viral dose was 0.0031 ppm.…”

Section: Introductionmentioning

confidence: 95%