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Low Toxicity β-cyclodextrin-caged 4,4'-bipyridinium-bis(siloxane): Synthesis and Evaluation

Low Toxicity β-cyclodextrin-caged 4,4'-bipyridinium-bis(siloxane): Synthesis and Evaluation

Narcisa Marangoci, Stelian S Maier, Rodinel Ardeleanu, Adina Arvinte, Adrian Fifere, Anca Roxana Petrovici, Alina Nicolescu, Valentin Nastasa, Mihai Mares, Sorin A Pasca, Ramona F Moraru, Mariana Pinteala, etc.

Chem Res Toxicol. 2014 Apr 21;27(4):546-57.

PMID: 24564239

Abstract:

The toxicity of viologens can be significantly reduced by including them in tight [2]rotaxane structures alongside β-cyclodextrin, thus turning them into candidates of pharmaceutical interest. Here, we report a synthesis pathway for a benign viologen, by capping a small β-cyclodextrin-caged molecule, the 4,4'-bipyridine, with minimal-length presynthesized axle-stopper segments of the propyl-3-pentamethyldisiloxane type. After 90 min from the oral administration to laboratory mice, the product concentration in the bloodstream reaches a value equivalent to 0.634% of the initial dose of 800 mg·kg(-1). As compared to the nude viologen having the same structure, which proved to be lethal in doses of 40 mg·kg(-1), the product induces reversible morphological changes in the liver, kidney, lung, and cerebellum, up to a dose of 400 mg·kg(-1), with higher dosages giving rise to a chronic slow evolution.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1438820	Pentamethyldisiloxane		1438-82-0	Price

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