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Blocking nitrosamine formation with polymers.

Y T Bao¹, R N Loeppky

¹Department of Chemistry, University of Missouri, Columbia 65211.

Chemical Research in Toxicology

|May 1, 1991

Summary

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Synthesized polymers with reactive groups effectively block nitrosamine formation. Hydrophilic polymers showed superior performance in scavenging nitrous acid, offering a new preventive toxicology approach.

Area of Science:

Polymer Chemistry
Toxicology
Organic Synthesis

Background:

Nitrosamines are potent animal carcinogens.
Preventing nitrosamine formation is crucial for public health.
Existing methods for nitrosamine inhibition have limitations.

Purpose of the Study:

To synthesize and evaluate polymers with nitrosation-reactive functional groups for blocking nitrosamine formation.
To compare the efficacy of hydrophobic and hydrophilic polymers in scavenging nitrosating agents.
To assess the potential of polymer-bound scavengers for preventive chemical toxicology.

Main Methods:

Synthesis of polymers with hydrophobic and hydrophilic backbones, including poly[(chloromethyl)styrene], poly(ethylene oxide-co-epichlorohydrin), chloromethylated cross-linked polystyrene, poly(ethylenimine) (PEI), and poly(acryloyl chloride).

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Derivatization of polymers with functional groups such as pyrrole, 2,5-dimethylpyrrole, 2-[(methylamino)methyl]pyrrole, and hydroquinone.

Testing the efficacy of synthesized polymers and PEI in blocking the nitrosation of morpholine by nitrous acid in aqueous solutions.

Evaluating the ability of polymers to scavenge nitrous acid and retain reaction products.

Main Results:

All synthesized polymers, including PEI, effectively blocked nitrosamine formation.
Hydrophilic polymers demonstrated superior performance in competing for nitrosating agents in aqueous solutions compared to hydrophobic polymers.
All tested polymers efficiently scavenged nitrous acid from aqueous solutions before amine addition.
Reaction products were retained on the polymer backbone, allowing for easy physical removal.

Conclusions:

Polymers functionalized with nitrosation-reactive groups are effective in preventing nitrosamine formation.
Hydrophilic polymers offer a promising strategy for scavenging nitrosating agents in aqueous environments.
This approach provides a novel method for the development of preventive chemical toxicology strategies, reducing exposure to carcinogenic N-nitroso compounds.