Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex.

Katz, David H.; Marcelletti, John F.; Khalil, Mohammed; Pope, L. S.; Katz, Lee R.

doi:10.1073/pnas.88.23.10825

Cited by 79 publications

(53 citation statements)

References 11 publications

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“…Recently, it was reported that certain mediumchain monoacyl glycerol esters and FFAs were bactericidal for Helicobacter pylori [42], and older literature reported that oleic acid had virucidal activity for membrane-enveloped mammalian viruses [43]. In addition, n-docosanol, a 22-carbon saturated fatty alcohol, has been reported to have antiviral activity against lipid-enveloped viruses, including herpes simplex viruses [44].…”

Section: Discussionmentioning

confidence: 99%

Palmitoleic Acid Isomer (C16:1Δ6) in Human Skin Sebum Is Effective against Gram-Positive Bacteria

Wille

Kydonieus²

2003

Skin Pharmacol Physiol

221

179

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The percent lipid composition of pooled human sebum analyzed by thin-layer chromatography was: ceramides (13%), fatty acid (47%), cholesterol (7%), cholesterol esters (2%), squalene (11%), triglycerides (3%), and wax esters (17%). Total sebum lipids (2– 4 mg/ml), sonicated into bacterial culture medium, caused 4- to 5-fold log reduction in growth of gram-positive bacteria, Staphylococcus aureus, Streptococcus salivarius and the anaerobe Fusobacterium nucleatum, but was ineffective against most gram-negative bacteria. Fractionation of the sebum lipids showed that both saturated and unsaturated fatty acids contained the bulk of the antimicrobial activity. Lauric acid (C12:0) was the most active saturated fatty acid. The unsaturated fatty acid, palmitoleic acid (C16:1Δ6, cPA) was both the most predominant monoene and the most active antimicrobial fatty acid. Purified cPA (>99%) yielded typical minimal inhibitory concentration (MIC) values of 10–20 µg/ml against gram-positive bacteria. Organically synthesized cPA isomer gave MIC values comparable to the natural material. Both natural and synthetic cPA were found to be the most active sebum lipid fraction in blocking the adherence of a pathogenic strain of Candida albicans to porcine stratum corneum. Ethanol in combination with cPA exerts a synergistic bactericidal activity against gram-negative pathogenic bacteria, including Pseudomonas aeruginosa, Propionibacterium acnes, Escherichia coli, and several methacillin-resistant strains of S. aureus. Palmitoleic acid may be useful in topical formulations for treatment of secondary gram-positive bacterial infections, as a gram-positive bacteria antimicrobial in wound dressings, and as a natural gram-positive antimicrobial preservative in skin and hair care products.

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Section: Discussionmentioning

confidence: 99%

Palmitoleic Acid Isomer (C16:1Δ6) in Human Skin Sebum Is Effective against Gram-Positive Bacteria

Wille

Kydonieus²

2003

Skin Pharmacol Physiol

221

179

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“…Studies with unsaturated alcohols and monoglycerides revealed peak activity with a triply double-bonded C 18 alcohol [11]. Docosanol, also called behenyl alcohol, is a saturated fatty alcohol which is used as an emollient and emulsifier in topical products and which was found to exert antiviral activity [12]. Docosanol was approved by the Food and Drug Administration as a topical treatment of orolabial herpes (Abreva©, Erazaban©).…”

Section: Discussionmentioning

confidence: 99%

“…Current evidence suggests that docosanol inhibits viral replication by interfering with viral entry into target cells. Interaction between the highly lipophilic compound and the target cell membranes may inhibit viral fusion and/or entry [12]. …”

Section: Discussionmentioning

confidence: 99%

A Randomized, Double-Blind, Placebo-Controlled Study to Test the Efficacy of Topical 2-Hydroxypropyl-Beta-Cyclodextrin in the Prophylaxis of Recurrent Herpes Labialis

Senti

Iannaccone²,

Graf³

et al. 2013

Dermatology

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Herpes labialis affects one third of the population. We evaluated the topical application of an antiviral compound, hydroxypropyl-β-cyclodextrin (2-HPβCD), in reducing herpes labialis relapses. In this double-blind, randomized, placebo-controlled trial, 40 patients were randomized to a polyethylene glycol (PEG) formulation containing 20% 2-HPβCD or to a vehicle control arm. The gel was applied to the lips twice daily for 6 months. The primary objective was reducing herpes relapses. Surprisingly, the drug group had significantly more relapses than the vehicle group (p = 0.003). While the median numbers of relapses in the preceding year were 12 in the vehicle group and 10 in the drug group, both groups experienced very few relapses during the 6-month treatment period, with a median of 0 in the vehicle group and a median of 2 in the drug group. The impressive reduction of relapses in both groups may be due to a placebo effect or due to the topical treatment with PEG.

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“…Extensive investigations on the herpes simplex virus in vivo and in vitro have shown that docosanol exerts potent inhibitory effects on the ability of the virus to infect target cells. Current evidence suggests that docosanol inhibits viral replication by interfering with early intracellular events surrounding viral entry into target cells [3]. However, for a few cell lines, the effects of docosanol are scarce.…”

Section: Introductionmentioning

confidence: 99%

“…Polycosanols have primarily been used to treat the herpes simplex virus (HSV-1) [1,2,3,4,5,6] and the respiratory syncytial virus [3]. Hyperproliferative skin lesions [7], which can be benign or malignant (keloids, skin cancer), can be treated and cured with these alcohols.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative evaluation of tall-oil docosanol and tetracosanol over CHO-K1 and human melanoma cells

Vergara

Olivares

Altamirano

2015

Electronic Journal of Biotechnology

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Background: Polycosanols derived from plant species have traditionally been used in medicine as antiproliferative agents for treating various viruses (primarily the herpes simplex virus). However, few studies have studied their effects on hyperproliferative cell lines. In this work, the antiproliferative capacity of polycosanols from tall-oil pitch, obtained from black liquor soaps in the kraft pulping process of cellulose (specifically from Pinus radiata, Pinus taede, and Eucalyptus globulus), was evaluated on CHO-K1 and CRL-1974 human melanoma cell lines. Results: The proliferative capacities and cell viabilities were measured for 72 and 140 h, respectively. Treatment with docosanol produced differential effects on the CHO-K1 and human melanoma cells and significantly affected their proliferation rates, but not their cell viabilities. Tetracosanol produced a significant negative effect on the proliferation of human melanoma cells, and this effect was less than that caused by docosanol. However, it had no effect on the proliferation of CHO-K1 cells and did not induce any significant effect on the viability of the studied cell lines. Conclusion: Docosanol and tetracosanol induced antiproliferative effects on the studied cell lines and exhibited significantly greater effects on the oncogenic cell lines. Prior to this study, the capacity of these polycosanols has never been investigated. Future studies will be necessary to determine their mechanisms of action on these cell systems.

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Antiviral activity of 1-docosanol, an inhibitor of lipid-enveloped viruses including herpes simplex.

Abstract: This article reports that 1-docosanol, a 22-

Cited by 79 publications

References 11 publications

Palmitoleic Acid Isomer (C16:1Δ6) in Human Skin Sebum Is Effective against Gram-Positive Bacteria

Palmitoleic Acid Isomer (C16:1Δ6) in Human Skin Sebum Is Effective against Gram-Positive Bacteria

A Randomized, Double-Blind, Placebo-Controlled Study to Test the Efficacy of Topical 2-Hydroxypropyl-Beta-Cyclodextrin in the Prophylaxis of Recurrent Herpes Labialis

Antiproliferative evaluation of tall-oil docosanol and tetracosanol over CHO-K1 and human melanoma cells

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