Radical-regulating and antiviral properties of ascorbic acid and its derivatives

Бринкевич, С. Д.; Бореко, Е. И.; Savinova, Olga V.; Pavlova, N. I.; Шадыро, О. И.

doi:10.1016/j.bmcl.2012.02.022

Cited by 13 publications

(8 citation statements)

References 25 publications

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“…To the best of our knowledge, the ability of this treatment to prevent HSK recurrence has not been reported previously. Supporting our finding is that some forms of ascorbic acid have antiviral properties: 2-O-glycoside of ascorbic acid displays marked antiviral properties against HSV-1, influenza, and poliovirus [ 19 ], while dehydro-ascorbic acid may affect HSV-1 multiplication after completion of viral DNA replication at the maturation stage [ 20 ]. Our previous study showed that the ascorbic acid concentration in the aqueous humor is increased by systemic ascorbic acid supplementation, and this increased ascorbic acid may have affected the recurrence of herpetic keratitis [ 21 ].…”

Section: Discussionmentioning

confidence: 59%

Clinical Features of Herpes Simplex Keratitis in a Korean Tertiary Referral Center: Efficacy of Oral Antiviral and Ascorbic Acid on Recurrence

Kim

Yoo

Park

et al. 2018

Korean J Ophthalmol

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PurposeTo describe the clinical manifestations of herpes simplex keratitis (HSK) in a tertiary referral center in South Korea and to determine whether ascorbic acid treatment prevents recurrence of herpetic epithelial keratitis.MethodsThis retrospective cohort study included all consecutive patients with herpetic keratitis referred to our center from January 2010 to January 2015. Clinical features, ocular complications, and recurrences were recorded.ResultsIn total, 149 eyes of the 133 patients (72 male and 61 female) were followed for an average of 24.6 ± 13.2 months. Sixteen (12.0%) patients had bilateral HSK. The most frequent HSK subtype was epithelial keratitis (49.7%), which was followed by stromal keratitis (23.5%). Epithelial keratitis was the most likely subtype to recur. Complications occurred in 122 (81.9%) eyes. The most common complication was corneal opacity. Recurrences were observed in 48 (32.2%) eyes. The recurrence rates were lower in the prophylactic oral antiviral agent group (16 / 48 eyes, 33.3% vs. 49 / 101 eyes, 48.5%) and the ascorbic acid treatment group (13 / 48 eyes, 27.1% vs. 81 / 101 eyes, 70.3%) compared with the groups without medications. Univariate logistic regression analysis revealed that both factors significantly reduced the risk of recurrence (acyclovir: odds ratio, 0.25; 95% confidence intervals, 0.12 to 0.51; ascorbic acid: odds ratio, 0.51; 95% confidence intervals, 0.20 to 0.91).ConclusionsThis retrospective study described the clinical findings of HSK in a tertiary referral center in South Korea. Prophylactic oral antiviral agent treatment and oral ascorbic acid administration may lower the risk of recurrence.

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Section: Discussionmentioning

confidence: 59%

Clinical Features of Herpes Simplex Keratitis in a Korean Tertiary Referral Center: Efficacy of Oral Antiviral and Ascorbic Acid on Recurrence

Kim

Yoo

Park

et al. 2018

Korean J Ophthalmol

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“…Curiously, excipients commonly classified as antioxidants, i.e., acetylcysteine, vitamin A, vitamin C (ascorbate), have been shown a variable grade of antiviral action [41,[45][46][47][48]. Of note, vitamin D has been shown to improve innate or therapeutic antiviral response to various viruses [49,50].…”

Section: Artificial Tearsmentioning

confidence: 99%

“…Overall, artificial tears have been shown to possess several mechanisms of antiviral action against a wide range of DNA or RNA viruses [ 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 ]. Interestingly, some polymer constituents (e.g., high molecular weight hyaluronic acid) and natural extracts (e.g., Ginkgo biloba ) have even shown that they can inhibit some viruses belonging to the Coronaviridae family (e.g., porcine parvovirus).…”

Section: Artificial Tearsmentioning

confidence: 99%

A Panel of Broad-Spectrum Antivirals in Topical Ophthalmic Medications from the Drug Repurposing Approach during and after the Coronavirus Disease 2019 Era

Napoli

Mangoni

Gentile

et al. 2020

JCM

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The coronavirus disease 2019 (COVID-19) represents a global concern of public health caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2). Its clinical manifestations are characterized by a heterogeneous group of symptoms and pictures (ranging from asymptomatic to lethal courses). The prevalence of conjunctivitis in patients with COVID-19 is at present controversial. Although it has been reported that only 0.9% developed signs of conjunctivitis, other report indicates that up to 31.6% of hospitalized patients had conjunctivitis. Considering the widespread use of topical ophthalmic medications (e.g., eye drops) by the general population, for various reasons (e.g., artificial tears, anti-glaucoma medications, topical antibiotics, etc.), the existence of their side effects as antiviral action should be investigated in-depth because it could possibly explain the aforementioned controversial data and represent a potential antiviral treatment for SARS-CoV-2 replication/diffusion on the ocular surface. Here, we discuss and elucidate the antiviral side effect of many eye drops and ophthalmic ointments commonly used for others purposes, thus showing that these secondary effects (not to be confused with the ‘adverse effects’) might be of primary importance in a number of viral infections (e.g., those for which there is no validated treatment protocol), according to a drug repurposing approach. Some active ingredients or excipients described here have activity against other types of viruses, thus suggesting potential broad-spectrum applications.

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“…As a downside, in its present non-substituted form, it is not capable of efficiently occupying the binding cavity. Interestingly, derivatives of ascorbic acid with pentacyclic triterpene extensions have been reported [ 59 , 60 ]. They interact with viral hemagglutinin, inhibiting the entry of the virus into the cell.…”

Section: Resultsmentioning

confidence: 99%

Five Novel Non-Sialic Acid-Like Scaffolds Inhibit In Vitro H1N1 and H5N2 Neuraminidase Activity of Influenza a Virus

et al. 2020

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Neuraminidase (NA) of influenza viruses enables the virus to access the cell membrane. It degrades the sialic acid contained in extracellular mucin. Later, it is responsible for releasing newly formed virions from the membrane of infected cells. Both processes become key functions within the viral cycle. Therefore, it is a therapeutic target for research of the new antiviral agents. Structure–activity relationships studies have revealed which are the important functional groups for the receptor–ligand interaction. Influenza virus type A NA activity was inhibited by five scaffolds without structural resemblance to sialic acid. Intending small organic compound repositioning along with drug repurposing, this study combined in silico simulations of ligand docking into the known binding site of NA, along with in vitro bioassays. The five proposed scaffolds are N-acetylphenylalanylmethionine, propanoic 3-[(2,5-dimethylphenyl) carbamoyl]-2-(piperazin-1-yl) acid, 3-(propylaminosulfonyl)-4-chlorobenzoic acid, ascorbic acid (vitamin C), and 4-(dipropylsulfamoyl) benzoic acid (probenecid). Their half maximal inhibitory concentration (IC50) was determined through fluorometry. An acidic reagent 2′-O-(4-methylumbelliferyl)-α-dN-acetylneuraminic acid (MUNANA) was used as substrate for viruses of human influenza H1N1 or avian influenza H5N2. Inhibition was observed in millimolar ranges in a concentration-dependent manner. The IC50 values of the five proposed scaffolds ranged from 6.4 to 73 mM. The values reflect a significant affinity difference with respect to the reference drug zanamivir (p < 0.001). Two compounds (N-acetyl dipeptide and 4-substituted benzoic acid) clearly showed competitive mechanisms, whereas ascorbic acid reflected non-competitive kinetics. The five small organic molecules constitute five different scaffolds with moderate NA affinities. They are proposed as lead compounds for developing new NA inhibitors which are not analogous to sialic acid.

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Radical-regulating and antiviral properties of ascorbic acid and its derivatives

Cited by 13 publications

References 25 publications

Clinical Features of Herpes Simplex Keratitis in a Korean Tertiary Referral Center: Efficacy of Oral Antiviral and Ascorbic Acid on Recurrence

Clinical Features of Herpes Simplex Keratitis in a Korean Tertiary Referral Center: Efficacy of Oral Antiviral and Ascorbic Acid on Recurrence

A Panel of Broad-Spectrum Antivirals in Topical Ophthalmic Medications from the Drug Repurposing Approach during and after the Coronavirus Disease 2019 Era

Five Novel Non-Sialic Acid-Like Scaffolds Inhibit In Vitro H1N1 and H5N2 Neuraminidase Activity of Influenza a Virus

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