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August 24, 2021

from American Chemical Society

In addition to antibodies and white blood cells, the immune system uses peptides to fight viruses and other pathogens. Synthetic peptides could strengthen this defense, but do not last long in the body, so researchers are developing stable peptide mimickers. Today scientists report success using mimetics known as peptoids to treat animals with herpes virus infections. These small synthetic molecules could one day cure or prevent many types of infections, including COVID-19.

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The researchers will present their results at the autumn meeting of the American Chemical Society (ACS).

“In the body, antimicrobial peptides such as LL-37 help keep viruses, bacteria, fungi, cancer cells and even parasites under control “Says Annelise Barron, Ph.D., one of the lead researchers on the project. But peptides are quickly eliminated by enzymes, so they are not ideal drug candidates. Instead, she and her colleagues emulated the key biophysical properties of LL-37 in smaller, more stable molecules called peptoids. « Peptoids are easy to make, » says Barron of Stanford University. « And unlike peptides, enzymes don’t break them down quickly, so they could be used in much smaller doses. »

Peptides are made up of short sequences of amino acids with side chains attached to carbon atoms in the backbone of the molecules. This structure is easily broken up by enzymes. In peptoids, the side chains are instead linked to nitrogen in the molecular backbone, forming a structure that resists enzymes. They were first published in 1992 by Ronald Zuckermann, Ph.D. prepared by Chiron Corp., later Barron’s postdoctoral fellow. Unlike other types of peptide mimetics that require tedious, multi-step organic chemistry to make, peptoids are easy and inexpensive to make using an automated synthesizer and readily available chemicals, she says. « They can be made almost as easily as making bread in a bread machine. »

Barron, Zuckermann, Gill Diamond, Ph.D., of the University of Louisville, and others founded Maxwell Biosciences to identify peptoids as clinical candidates to prevent or treat viral infections. They recently reported results with their latest peptoid sequences that are less toxic to humans than previous versions. In laboratory dishes, the compounds inactivated SARS-CoV-2, which causes COVID-19, and Herpes Simplex Virus-1 (HSV-1), which causes cold sores, making the viruses unable to infect cultured human cells.

Now the researchers are reporting in vivo results showing that the peptoids safely prevented herpes infections in mice when dabbed on their lips. Diamond’s team is conducting additional experiments to confirm the mouse results. In addition, they will study the effectiveness of the peptoids against strains of HSV-1 that are resistant to acyclovir, the best antiviral treatment currently approved by the US Food and Drug Administration for the disease, says Barron.

The researchers are also preparing to test peptoids in mice for activity against SARS-CoV-2. « COVID-19 infection affects the whole body as soon as someone is really sick, so we’re going to do this test intravenously and look at the delivery to the lungs, » says Barron.

But these antimicrobial molecules could do a lot more have more uses. Stanford is currently working to study its effects on ear and lung infections. And Barron has sent peptoid samples to experts in other laboratories to be tested for a range of viruses, with promising results in laboratory tray studies against influenza, the common cold virus, and hepatitis B and C. « In their in vitro studies, one team found that two of the peptoids were the most potent antivirals ever identified against MERS and older SARS coronaviruses, « says Barron. Other laboratories are testing the peptoids as antifungal drugs for the respiratory tract and colon, and as anti-infectious coatings for contact lenses, catheters, and implanted hip and knee joints.

Diamond and Barron are studying how these broadband compounds work. They appear to penetrate and break open the virus envelope and also bind to the virus’s RNA or DNA. This multi-pronged mechanism has the advantage of inactivating the virus, as opposed to traditional antivirals, which slow virus replication but still allow viruses to infect cells, says Barron. It also makes it less likely that pathogens will develop resistance.

Barron anticipates clinical trials will begin later this year. If successful, she says, peptoids could be given preventively – for example, before air travel to protect a passenger from COVID-19 – or after an infection has taken hold, such as when a person experiences the tingling tingling of an approaching cold sore.

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