A new chemical tool for studying the dual nature of toxic formaldehyde

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Structures of phthalimide-derived HCHO-releasing compounds. All compounds contain a phthalimide unit linked to a carboxylate oxygen via a methylene group. Esterase-mediated hydrolysis of the resulting ester yields the free carboxylate, thalimide, and HCHO. PFFor, PFAc, PFProp, PFPhen and PFBz are all soluble in water at 100 mM in 10% v/v DMSO. POxoBut and PGlycAc (dashed box) are non-HCHO-releasing analogs of PFAc. debt: Chemical Science (2023) DOI: 10.1039/D3SC02867D

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Structures of phthalimide-derived HCHO-releasing compounds. All compounds contain a phthalimide unit linked to a carboxylate oxygen via a methylene group. Esterase-mediated hydrolysis of the resulting ester yields the free carboxylate, thalimide, and HCHO. PFFor, PFAc, PFProp, PFPhen and PFBz are all soluble in water at 100 mM in 10% v/v DMSO. POxoBut and PGlycAc (dashed box) are non-HCHO-releasing analogs of PFAc. debt: Chemical Science (2023) DOI: 10.1039/D3SC02867D

Compounds developed by University of Leicester chemists aim to reveal the dual nature of formaldehyde, which is known to cause cancer but is believed to play an important role in our biology.

The compounds are described in a new study in the journal Chemical Science And will allow scientists to study a chemical that exists in all living things, but which has so far proved too volatile and too reactive to be easily studied.

Formaldehyde is widespread in nature and has a variety of uses, including as a glue and disinfecting agent famously used in Damien Hirst’s artwork. It is a human toxin and is also known to be carcinogenic (capable of causing cancer) in high doses. Formaldehyde is produced in our cells and is present in animals and plants. Scientists are seeing growing evidence that formaldehyde plays an important role in our biology despite its toxicity.

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However, studying formaldehyde inside a cell is challenging due to its volatility and reactivity. Understanding how this molecule is toxic and carcinogenic is important because it will help scientists find ways to prevent or treat those effects.

To study its effect on our cells more precisely, a team from the University of Leicester, along with collaborators from the University of Oxford, has developed a new library of compounds designed to release formaldehyde in controlled doses. consequences. They are partly inspired by compounds used in the cosmetics industry that release small amounts of formaldehyde over time.

From the University of Leicester’s Institute of Structural and Chemical Biology, Dr. Richard Hopkinson said, „The scientific community desperately needs ways to deliver formaldehyde in a scalable, controllable and reproducible manner. The problem is that formaldehyde’s high reactivity and volatility make it very challenging. .”

Formaldehyde has been linked to various types of cancer, particularly nose and throat cancers caused by inhalation of formaldehyde, but it is often difficult for scientists to make a firm link between formaldehyde exposure and the onset of disease.

However, Dr. Hopkins notes that there is growing evidence that formaldehyde plays a role in our metabolism. „We’re always producing formaldehyde in ourselves, but it’s a very reactive chemical, and most things in biology are not reactive.”

„We think it might actually be an important nutrient, not just a toxin, but too much or too little formaldehyde can put us on the brink of disease. If we can figure out exactly what formaldehyde does inside cells, we hope. We can begin to answer these important questions.”

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More information:
Vicki L. Emms et al, N-Acyloxymethyl-phthalimides confer genotoxic formaldehyde to human cells, Chemical Science (2023) DOI: 10.1039/D3SC02867D

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Chemical Science


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