Fatty Alcohols, Fatty Acids, and Fatty Acid Esters as Penetration Enhancers

Babu, R. Jayachandra; Chen, Li; Kanikkannan, Narayanasamy

doi:10.1007/978-3-662-47039-8_9

Cited by 12 publications

(7 citation statements)

References 100 publications

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“…A prolonged penetration is desirable to hydrate the skin and deliver agents. However, formulations that showed great permeation also showed an increase in skin irritations ( 114 ). There is a constant evolution of cosmetic products on the market and new products are developed that use liposomes and lipid nanoparticles as carriers for cosmetic agents ( 115 ).…”

Section: Discussionmentioning

confidence: 99%

Mammalian derived lipocalin and secretoglobin respiratory allergens strongly bind ligands with potentially immune modulating properties

et al. 2022

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Allergens from furry animals frequently cause sensitization and respiratory allergic diseases. Most relevant mammalian respiratory allergens belong either to the protein family of lipocalins or secretoglobins. Their mechanism of sensitization remains largely unresolved. Mammalian lipocalin and secretoglobin allergens are associated with a function in chemical communication that involves abundant secretion into the environment, high stability and the ability to transport small volatile compounds. These properties are likely to contribute concomitantly to their allergenic potential. In this study, we aim to further elucidate the physiological function of lipocalin and secretoglobin allergens and link it to their sensitizing capacity, by analyzing their ligand-binding characteristics. We produced eight major mammalian respiratory allergens from four pet species in E.coli and compared their ligand-binding affinities to forty-nine ligands of different chemical classes by using a fluorescence-quenching assay. Furthermore, we solved the crystal-structure of the major guinea pig allergen Cav p 1, a typical lipocalin. Recombinant lipocalin and secretoglobin allergens are of high thermal stability with melting temperatures ranging from 65 to 90°C and strongly bind ligands with dissociation constants in the low micromolar range, particularly fatty acids, fatty alcohols and the terpene alcohol farnesol, that are associated with potential semiochemical and/or immune-modulating functions. Through the systematic screening of respiratory mammalian lipocalin and secretoglobin allergens with a large panel of potential ligands, we observed that total amino acid composition, as well as cavity shape and volume direct affinities to ligands of different chemical classes. Therefore, we were able to categorize lipocalin allergens over their ligand-binding profile into three sub-groups of a lipocalin clade that is associated with functions in chemical communication, thus strengthening the function of major mammalian respiratory allergens as semiochemical carriers. The promiscuous binding capability of hydrophobic ligands from environmental sources warrants further investigation regarding their impact on a molecule's allergenicity.

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Section: Discussionmentioning

confidence: 99%

Mammalian derived lipocalin and secretoglobin respiratory allergens strongly bind ligands with potentially immune modulating properties

et al. 2022

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“…OA is believed to increase diffusivity by disordering SC lipids [26]. Structural features such as the unsaturation and the cis isomer configuration are essential to maximise the disruption caused by OA within the lipid bilayers of the SC and its penetration enhancer activity [27, 28]. EU is reported to be the most promising enhancer for polar and water-soluble drugs among the terpenes [29], and is favoured for its relatively low toxicity and irritancy [30].…”

Section: Discussion/conclusionmentioning

confidence: 99%

Permeation Mechanism of Caffeine and Naproxen through in vitro Human Epidermis: Effect of Vehicles and Penetration Enhancers

Abd

Benson

Mohammed

et al. 2019

Skin Pharmacol Physiol

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Background/Aims: The mechanisms by which permeation enhancers increase human skin permeation of caffeine and naproxen were assessed in vitro. Methods: Active compound solubility in the vehicles and in the stratum corneum (SC), active compound flux across epidermal membranes and uptake of active and vehicle components into the SC were measured. The effect of vehicle pH on the permeation of caffeine and naproxen was also determined. Results: Oleic acid and eucalyptol significantly enhanced the skin penetration of caffeine and naproxen, compared to aqueous controls. Naproxen permeation was increased from vehicles with pH presenting more ionized naproxen. Caffeine maximum flux enhancement was associated with an increase in caffeine SC solubility and skin diffusivity, whereas for naproxen a penetration enhancer/vehicle-induced increase in solubility in the SC correlated with an increase in maximum flux. SC solubility was related to experimentally determined active uptake, which was in turn predicted by vehicle uptake and active compound solubility in the vehicle. Conclusion: A permeation enhancer-induced alteration in diffusivity, rather than effects on SC solubility, was the main driving force behind increases in permeation flux of the hydrophilic molecule caffeine. For the more the lipophilic molecule naproxen, increased SC solubility drove the increases in permeation flux.

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“…İlaçların difüzitesini ve partisyonunu artırırlar. 23 Alkoller, yağ alkolleri ve glikoller: Genel olarak SK'nin çözücü özelliklerini değiştirerek, ilaç çözünürlüğünü artırarak ve SK'nin hücreler arası lipid geometrisini bozarak etki ederler. 16 Etanol ve propilen glikol gibi çözücüler yalnızca penetrasyon artırıcılar olarak değil, aynı zamanda lipofilik ilaçların çözünürlüğünü artırmak için kosolvan olarak da kullanılmaktadır.…”

Section: Ki̇myasal Penetrasyon Artiricilarunclassified

“…Penetrasyon artışı, alkil zincirlerinin akışkanlığının artmasına neden olan polar baş grup bölgesi ile yağ alkollerinin etkileşimlerinin bir sonucudur. 23 Sürfaktanlar: SK içindeki lipidleri çözerek ve protein denatürasyonunu indükleyerek SK'nin şişmesine sebep olarak ilaç penetrasyonunu artırırlar. Sodyum lauril sülfat gibi anyonik yüzey aktif maddeler derinin bariyer fonksiyonunu bozarak SK'deki lipidlere ve proteinlere zarar verir.…”

Section: Ki̇myasal Penetrasyon Artiricilarunclassified

Strategies to Enhance Drug Pass in Transdermal and Dermal Therapeutic Systems: Traditional Review

ÖZCAN,

İLBASMIŞ TAMER

2023

J Lit Pharm Sci

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ÖZET Transdermal ve dermal terapötik sistemlerin diğer ilaç uygulama yollarına göre birçok avantajı bulunmaktadır. Transdermal yol, ilaçların oral yoldan verildiğinde ilk geçiş etkisi gibi mide-bağırsak sisteminde ortaya çıkabilecek sakıncaları önleyebilir, böylece ilaçların biyoyararlanımı artırır. Subkütan enjeksiyona göre daha düşük enfeksiyon riski ve maliyeti vardır. Hasta uyuncu daha yüksektir. Dermal uygulama ise ağrı ve sistemik yan etkileri en aza indirmesi ve kullanım kolaylığı gibi avantajlara sahiptir. Deriden ilaç geçişi hücre içi, hücreler arası, transapendageal ve gözenek yolu ile difüzyonla gerçekleşmektedir. Transdermal ve dermal sistemlerde karşılaşılan en büyük zorluklardan biri, ilaçların deriden geçişlerinin yeterli düzeyde olmamasıdır. Epidermisin en üst katmanı olan stratum korneum (SK), ilaç geçişine karşı engel özelliği göstermektedir. SK'nin hücre dışı lipid ile zenginleştirilmiş matrisi hidrofilik ilaçların geçişini sınırlamakta, lipofilik ilaçların ise birikip yavaşça salınmasına sebep olabilmektedir. Bu durum aktif bileşenlerin biyoyararlanımını düşürmektedir. İlaç taşıyıcı sistemlerin sağladığı avantajlardan faydalanarak, SK'nin engel işlevini aşmak için çeşitli aktif ve pasif yöntemler geniş çapta incelenmiştir. Bu derleme makalede de transdermal ve dermal terapötik sistemlerde ilaç geçişini artırma yöntemleri incelenmiştir. Birinci nesil transdermal ve dermal ilaç taşıyıcı sistemlerde ilaç geçişi çok sınırlıdır. Esas olarak ikinci nesil yöntemlerde ilaç geçişinin artırılması hedeflenmektedir. Bu kapsamda; ilaç-ilaç etkileşimi, SK modifikasyonu, ilaç taşıyıcı sistemler, enerji odaklı sistemler ve SK'nin atlatılması yöntemlerini içermektedir. İkincil nesildeki yöntemlerin birleştirilmesi ise üçüncü nesli oluşturmaktadır. Bu tür yenilikçi yaklaşımlar uygulanan ilaçları doz, maliyet ve terapötik etkinlik açısından daha avantajlı hâle getirebilir. Bu makale kapsamında özellikle ikinci nesil başlığı altında yer alan yöntemler özetlenerek, incelenmiştir. Anah tar Ke li me ler: Kutanöz uygulama; deri emilimi; iyontoforez; elektroporasyon; ilaç taşıyıcı sistem ABS TRACT Transdermal, dermal systems therapeutic systems have many advantages over other drug delivery routes. Transdermal route can prevent problems that may occur in gastrointestinal system such as first pass effect when the drugs are administered orally, increase bioavailability of drugs. It has lower infection risk, cost compared to subcutaneous injection. Patient compliance is higher. Dermal application has advantages such as minimizing pain, systemic side effects, ease of use. Drug passage through skin occurs by diffusion through intracellular, intercellular, transappendageal, pore routes. One of the biggest difficulties encountered in transdermal, dermal systems is insufficient penetration of drugs through skin. Stratum corneum (SC), uppermost layer of the epidermis, acts as barrier against drug penetration. Extracellular lipid-enriched matrix of SC restricts passage of hydrophilic drugs, causing accumulation, slow release of ...

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Fatty Alcohols, Fatty Acids, and Fatty Acid Esters as Penetration Enhancers

Cited by 12 publications

References 100 publications

Mammalian derived lipocalin and secretoglobin respiratory allergens strongly bind ligands with potentially immune modulating properties

Mammalian derived lipocalin and secretoglobin respiratory allergens strongly bind ligands with potentially immune modulating properties

Permeation Mechanism of Caffeine and Naproxen through in vitro Human Epidermis: Effect of Vehicles and Penetration Enhancers

Strategies to Enhance Drug Pass in Transdermal and Dermal Therapeutic Systems: Traditional Review

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