Design, synthesis and characterization of linear unnatural amino acids for skin moisturization
Objectives This work aimed to design, synthesize and characterize replacement natural moisturizing factor (NMF) composed of modified hygroscopic linear amino acids to pre‐empt or repair skin barrier dysfunction. Methods Following synthesis and characterization, thermo‐gravimetric analysis and quantu...
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| creator | Arezki, N. R. Williams, A. C. Cobb, A. J. A. Brown, M. B. |
| description | Objectives
This work aimed to design, synthesize and characterize replacement natural moisturizing factor (NMF) composed of modified hygroscopic linear amino acids to pre‐empt or repair skin barrier dysfunction.
Methods
Following synthesis and characterization, thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water binding to the new compounds. Deliquescence relative humidity demonstrated the water‐scavenging ability of the compounds, whereas snake skin moisturizing studies showed they increased water uptake into snake skin.
Results
From thermal analysis, N‐hydroxyglycine showed greatest water‐holding capacity followed by N‐hydroxyserine, l‐homoserine and α‐hydroxyglycine; coupled with quantum mechanics molecular modelling, between 8 and 12 molecules of water could associate with each molecule of either N‐hydroxyglycine, N‐hydroxyserine or l‐homoserine. All of our modified amino acids were efficacious and induced similar or greater water uptake compared with the established moisturizing compounds hyaluronic acid, glycerine and urea in snake skin. Incorporated at 10% in Oilatum, N‐hydroxyserine induced >200% greater moisture uptake into dry snake skin compared to treatment with water alone, with efficacy related to the molecule structure and ability to bind to 12 water molecules. Oilatum cream spiked with all our unnatural amino acid hydrotropes increased water uptake into snake skin compared with Oilatum alone.
The compound series was designed to elucidate some structure – efficacy relationships. Amino acid chirality did not affect the water‐holding capacity but did affect uptake into skin. Compounds with high melting points and bond energies tended to decrease water‐holding capacity. With isosteric replacement, the more electronegative atoms gave greater water‐holding capacities.
Conclusions
This work demonstrates the potential of unnatural amino acid hydrotropes as skin moisturizers and has developed some predictive ‘rules’ for further design and refinement of chemical structures.
Résumé
Objectifs
Ce travail vise à concevoir, synthétiser et 0 caractériser le remplacement du Natural Moisturising Factor (NMF) composé d'acides aminés linéaires hygroscopiques modifiés pour anticiper ou réparer un dysfonctionnement de la barrière cutanée.
Methode
Après la synthèse et la caractérisation, l'analyse thermo‐gravimétrique et la modélisation par la mécanique quantique moléculaire permettent de quantifier et représenter l |
| doi_str_mv | 10.1111/ics.12351 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5244679</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1826712135</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4811-7ccb4566953f786a9c321d154d6207167a5654aa3ec7133ba124bcb9d59299553</originalsourceid><addsrcrecordid>eNp1kU2P0zAQhi0EomXhwB9Y-QgS2c34K_FlJVS-KlXiAFyxJo7TeknsXTsBlV9PSksFB3wZS_PMMyO9hDyH8grmd-1tvgLGJTwgSxCqLpjQ4iFZliBYIYXiC_Ik59uyLIWu-WOyYBWvS6brJfn6xmW_Da9o3odxN_8zxdBSu8OEdnTJ_8TRx0BjR3sfHCY6hYDjlLCnOPgQKVrfZtrFRPM3H-gQfZ7bp7mn5FGHfXbPTvWCfHn39vPqQ7H5-H69er0prKgBisraRkiltORdVSvUljNoQYpWsbICVaFUUiByZyvgvEFgorGNbqVmWkvJL8jN0Xs3NYNrrQvjfKG5S37AtDcRvfm3E_zObON3I5kQqtKz4MVJkOL95PJoBp-t63sMLk7ZQM1UBQz4YdfLI2pTzDm57rwGSnPIw8x5mN95zOzl33edyT8BzMD1Efjhe7f_v8msV5-Oyl8-jJZH</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1826712135</pqid></control><display><type>article</type><title>Design, synthesis and characterization of linear unnatural amino acids for skin moisturization</title><source>MEDLINE</source><source>Access via Wiley Online Library</source><creator>Arezki, N. R. ; Williams, A. C. ; Cobb, A. J. A. ; Brown, M. B.</creator><creatorcontrib>Arezki, N. R. ; Williams, A. C. ; Cobb, A. J. A. ; Brown, M. B.</creatorcontrib><description>Objectives
This work aimed to design, synthesize and characterize replacement natural moisturizing factor (NMF) composed of modified hygroscopic linear amino acids to pre‐empt or repair skin barrier dysfunction.
Methods
Following synthesis and characterization, thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water binding to the new compounds. Deliquescence relative humidity demonstrated the water‐scavenging ability of the compounds, whereas snake skin moisturizing studies showed they increased water uptake into snake skin.
Results
From thermal analysis, N‐hydroxyglycine showed greatest water‐holding capacity followed by N‐hydroxyserine, l‐homoserine and α‐hydroxyglycine; coupled with quantum mechanics molecular modelling, between 8 and 12 molecules of water could associate with each molecule of either N‐hydroxyglycine, N‐hydroxyserine or l‐homoserine. All of our modified amino acids were efficacious and induced similar or greater water uptake compared with the established moisturizing compounds hyaluronic acid, glycerine and urea in snake skin. Incorporated at 10% in Oilatum, N‐hydroxyserine induced >200% greater moisture uptake into dry snake skin compared to treatment with water alone, with efficacy related to the molecule structure and ability to bind to 12 water molecules. Oilatum cream spiked with all our unnatural amino acid hydrotropes increased water uptake into snake skin compared with Oilatum alone.
The compound series was designed to elucidate some structure – efficacy relationships. Amino acid chirality did not affect the water‐holding capacity but did affect uptake into skin. Compounds with high melting points and bond energies tended to decrease water‐holding capacity. With isosteric replacement, the more electronegative atoms gave greater water‐holding capacities.
Conclusions
This work demonstrates the potential of unnatural amino acid hydrotropes as skin moisturizers and has developed some predictive ‘rules’ for further design and refinement of chemical structures.
Résumé
Objectifs
Ce travail vise à concevoir, synthétiser et 0 caractériser le remplacement du Natural Moisturising Factor (NMF) composé d'acides aminés linéaires hygroscopiques modifiés pour anticiper ou réparer un dysfonctionnement de la barrière cutanée.
Methode
Après la synthèse et la caractérisation, l'analyse thermo‐gravimétrique et la modélisation par la mécanique quantique moléculaire permettent de quantifier et représenter les nouveaux composés liés à l'eau. A humidité relative on démontre la capacité des composés piégeant l'eau, tandis que les études d'hydratation de la peau de serpent ont montré qu'ils ont augmenté l'absorption de l'eau dans la peau de serpent.
Résultats
De l'analyse thermique, la N‐hydroxyglycine a montré la plus grande capacité de rétention d'eau suivie de N‐hydroxyserine, l‐homosérine et α‐hydroxyglycine; couplée avec la modélisation mécanique quantique moléculaire, entre 8 et 12 molécules d'eau pourrait s'associer à chaque molécule de l'une des N‐hydroxyglycine, N‐hydroxyserine ou lL‐homosérine. Tous les acides aminés modifiés sont efficaces et conduisent à une absorbance d'eau similaire ou supérieure par rapport aux composés hydratants établis tels que l'acide hyaluronique, la glycérine et l'urée dans la peau de serpent. Incorporée à 10% dans Oilatum, la N‐hydroxyserine induit une plus grande absorption de l'humidité dans la peau de serpent sèche de 200% par rapport au traitement avec de l'eau seule, avec une efficacité liée à la structure des molécules et la capacité de se lier à 12 molécules d'eau. Une crème Oilatum renforcée avec tous nos hydrotropes d'acides aminés non naturels augmente l'absorption d'eau dans la peau de serpent par rapport à Oilatum seul.
La série des composés a été conçue pour élucider certaines relations structure ‐ efficacité. La chiralité des acides aminés n'a pas affecté la capacité de rétention d'eau, mais a affecté l'absorption dans la peau. Les composés ayant des points de fusion et des énergies de liaison ont tendance à diminuer la capacité de rétention d'eau. Avec le remplacement isostérique, les atomes plus électronégatifs ont donné une plus grande capacité de rétention d'eau.
Conclusions
Ce travail démontre le potentiel des acides aminés non naturels hydrotropes comme hydratants pour la peau et a développé des «règles» de prédiction pour poursuivre la conception et l'amélioration des structures chimiques.
Chemically‐modified linear amino acids, based on the Natural Moisturising Factor constituents glycine and serine, were designed, synthesised and evaluated as moisturisers. Deliquescence relative humidity demonstrated increased water‐scavenging ability of the compounds compared to their parent amino acids whereas thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water‐binding to the new hydrotropes. Moisturisation was demonstrated in a snake skin model, and together with results from natural amino acids, structure‐efficacy relationships were developed for the water‐holding abilities of linear amino acid moisturisers.</description><identifier>ISSN: 0142-5463</identifier><identifier>EISSN: 1468-2494</identifier><identifier>DOI: 10.1111/ics.12351</identifier><identifier>PMID: 27380298</identifier><language>eng</language><publisher>England: John Wiley and Sons Inc</publisher><subject>Amino Acids - chemistry ; Animals ; chemical synthesis ; deliquescence relative humidity ; delivery ; Humans ; hygroscopic ; Magnetic Resonance Spectroscopy ; natural moisturizing factor ; Original ; Powder Diffraction ; skin barrier ; Skin Physiological Phenomena ; Snakes ; Spectrophotometry, Infrared ; Thermogravimetry ; Water Loss, Insensible</subject><ispartof>International journal of cosmetic science, 2017-02, Vol.39 (1), p.72-82</ispartof><rights>2016 The Authors. published by John Wiley & Sons Ltd on behalf of Society of Cosmetic Scientists and Société Française de Cosmétologie.</rights><rights>2016 The Authors. International Journal of Cosmetic Science published by John Wiley & Sons Ltd on behalf of Society of Cosmetic Scientists and Société Française de Cosmétologie.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4811-7ccb4566953f786a9c321d154d6207167a5654aa3ec7133ba124bcb9d59299553</citedby><cites>FETCH-LOGICAL-c4811-7ccb4566953f786a9c321d154d6207167a5654aa3ec7133ba124bcb9d59299553</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1111%2Fics.12351$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1111%2Fics.12351$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,315,781,785,886,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27380298$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Arezki, N. R.</creatorcontrib><creatorcontrib>Williams, A. C.</creatorcontrib><creatorcontrib>Cobb, A. J. A.</creatorcontrib><creatorcontrib>Brown, M. B.</creatorcontrib><title>Design, synthesis and characterization of linear unnatural amino acids for skin moisturization</title><title>International journal of cosmetic science</title><addtitle>Int J Cosmet Sci</addtitle><description>Objectives
This work aimed to design, synthesize and characterize replacement natural moisturizing factor (NMF) composed of modified hygroscopic linear amino acids to pre‐empt or repair skin barrier dysfunction.
Methods
Following synthesis and characterization, thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water binding to the new compounds. Deliquescence relative humidity demonstrated the water‐scavenging ability of the compounds, whereas snake skin moisturizing studies showed they increased water uptake into snake skin.
Results
From thermal analysis, N‐hydroxyglycine showed greatest water‐holding capacity followed by N‐hydroxyserine, l‐homoserine and α‐hydroxyglycine; coupled with quantum mechanics molecular modelling, between 8 and 12 molecules of water could associate with each molecule of either N‐hydroxyglycine, N‐hydroxyserine or l‐homoserine. All of our modified amino acids were efficacious and induced similar or greater water uptake compared with the established moisturizing compounds hyaluronic acid, glycerine and urea in snake skin. Incorporated at 10% in Oilatum, N‐hydroxyserine induced >200% greater moisture uptake into dry snake skin compared to treatment with water alone, with efficacy related to the molecule structure and ability to bind to 12 water molecules. Oilatum cream spiked with all our unnatural amino acid hydrotropes increased water uptake into snake skin compared with Oilatum alone.
The compound series was designed to elucidate some structure – efficacy relationships. Amino acid chirality did not affect the water‐holding capacity but did affect uptake into skin. Compounds with high melting points and bond energies tended to decrease water‐holding capacity. With isosteric replacement, the more electronegative atoms gave greater water‐holding capacities.
Conclusions
This work demonstrates the potential of unnatural amino acid hydrotropes as skin moisturizers and has developed some predictive ‘rules’ for further design and refinement of chemical structures.
Résumé
Objectifs
Ce travail vise à concevoir, synthétiser et 0 caractériser le remplacement du Natural Moisturising Factor (NMF) composé d'acides aminés linéaires hygroscopiques modifiés pour anticiper ou réparer un dysfonctionnement de la barrière cutanée.
Methode
Après la synthèse et la caractérisation, l'analyse thermo‐gravimétrique et la modélisation par la mécanique quantique moléculaire permettent de quantifier et représenter les nouveaux composés liés à l'eau. A humidité relative on démontre la capacité des composés piégeant l'eau, tandis que les études d'hydratation de la peau de serpent ont montré qu'ils ont augmenté l'absorption de l'eau dans la peau de serpent.
Résultats
De l'analyse thermique, la N‐hydroxyglycine a montré la plus grande capacité de rétention d'eau suivie de N‐hydroxyserine, l‐homosérine et α‐hydroxyglycine; couplée avec la modélisation mécanique quantique moléculaire, entre 8 et 12 molécules d'eau pourrait s'associer à chaque molécule de l'une des N‐hydroxyglycine, N‐hydroxyserine ou lL‐homosérine. Tous les acides aminés modifiés sont efficaces et conduisent à une absorbance d'eau similaire ou supérieure par rapport aux composés hydratants établis tels que l'acide hyaluronique, la glycérine et l'urée dans la peau de serpent. Incorporée à 10% dans Oilatum, la N‐hydroxyserine induit une plus grande absorption de l'humidité dans la peau de serpent sèche de 200% par rapport au traitement avec de l'eau seule, avec une efficacité liée à la structure des molécules et la capacité de se lier à 12 molécules d'eau. Une crème Oilatum renforcée avec tous nos hydrotropes d'acides aminés non naturels augmente l'absorption d'eau dans la peau de serpent par rapport à Oilatum seul.
La série des composés a été conçue pour élucider certaines relations structure ‐ efficacité. La chiralité des acides aminés n'a pas affecté la capacité de rétention d'eau, mais a affecté l'absorption dans la peau. Les composés ayant des points de fusion et des énergies de liaison ont tendance à diminuer la capacité de rétention d'eau. Avec le remplacement isostérique, les atomes plus électronégatifs ont donné une plus grande capacité de rétention d'eau.
Conclusions
Ce travail démontre le potentiel des acides aminés non naturels hydrotropes comme hydratants pour la peau et a développé des «règles» de prédiction pour poursuivre la conception et l'amélioration des structures chimiques.
Chemically‐modified linear amino acids, based on the Natural Moisturising Factor constituents glycine and serine, were designed, synthesised and evaluated as moisturisers. Deliquescence relative humidity demonstrated increased water‐scavenging ability of the compounds compared to their parent amino acids whereas thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water‐binding to the new hydrotropes. Moisturisation was demonstrated in a snake skin model, and together with results from natural amino acids, structure‐efficacy relationships were developed for the water‐holding abilities of linear amino acid moisturisers.</description><subject>Amino Acids - chemistry</subject><subject>Animals</subject><subject>chemical synthesis</subject><subject>deliquescence relative humidity</subject><subject>delivery</subject><subject>Humans</subject><subject>hygroscopic</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>natural moisturizing factor</subject><subject>Original</subject><subject>Powder Diffraction</subject><subject>skin barrier</subject><subject>Skin Physiological Phenomena</subject><subject>Snakes</subject><subject>Spectrophotometry, Infrared</subject><subject>Thermogravimetry</subject><subject>Water Loss, Insensible</subject><issn>0142-5463</issn><issn>1468-2494</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><sourceid>EIF</sourceid><recordid>eNp1kU2P0zAQhi0EomXhwB9Y-QgS2c34K_FlJVS-KlXiAFyxJo7TeknsXTsBlV9PSksFB3wZS_PMMyO9hDyH8grmd-1tvgLGJTwgSxCqLpjQ4iFZliBYIYXiC_Ik59uyLIWu-WOyYBWvS6brJfn6xmW_Da9o3odxN_8zxdBSu8OEdnTJ_8TRx0BjR3sfHCY6hYDjlLCnOPgQKVrfZtrFRPM3H-gQfZ7bp7mn5FGHfXbPTvWCfHn39vPqQ7H5-H69er0prKgBisraRkiltORdVSvUljNoQYpWsbICVaFUUiByZyvgvEFgorGNbqVmWkvJL8jN0Xs3NYNrrQvjfKG5S37AtDcRvfm3E_zObON3I5kQqtKz4MVJkOL95PJoBp-t63sMLk7ZQM1UBQz4YdfLI2pTzDm57rwGSnPIw8x5mN95zOzl33edyT8BzMD1Efjhe7f_v8msV5-Oyl8-jJZH</recordid><startdate>201702</startdate><enddate>201702</enddate><creator>Arezki, N. R.</creator><creator>Williams, A. C.</creator><creator>Cobb, A. J. A.</creator><creator>Brown, M. B.</creator><general>John Wiley and Sons Inc</general><scope>24P</scope><scope>WIN</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>201702</creationdate><title>Design, synthesis and characterization of linear unnatural amino acids for skin moisturization</title><author>Arezki, N. R. ; Williams, A. C. ; Cobb, A. J. A. ; Brown, M. B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4811-7ccb4566953f786a9c321d154d6207167a5654aa3ec7133ba124bcb9d59299553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Amino Acids - chemistry</topic><topic>Animals</topic><topic>chemical synthesis</topic><topic>deliquescence relative humidity</topic><topic>delivery</topic><topic>Humans</topic><topic>hygroscopic</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>natural moisturizing factor</topic><topic>Original</topic><topic>Powder Diffraction</topic><topic>skin barrier</topic><topic>Skin Physiological Phenomena</topic><topic>Snakes</topic><topic>Spectrophotometry, Infrared</topic><topic>Thermogravimetry</topic><topic>Water Loss, Insensible</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arezki, N. R.</creatorcontrib><creatorcontrib>Williams, A. C.</creatorcontrib><creatorcontrib>Cobb, A. J. A.</creatorcontrib><creatorcontrib>Brown, M. B.</creatorcontrib><collection>Wiley Online Library (Open Access Collection)</collection><collection>Wiley Online Library (Open Access Collection)</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>International journal of cosmetic science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Arezki, N. R.</au><au>Williams, A. C.</au><au>Cobb, A. J. A.</au><au>Brown, M. B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and characterization of linear unnatural amino acids for skin moisturization</atitle><jtitle>International journal of cosmetic science</jtitle><addtitle>Int J Cosmet Sci</addtitle><date>2017-02</date><risdate>2017</risdate><volume>39</volume><issue>1</issue><spage>72</spage><epage>82</epage><pages>72-82</pages><issn>0142-5463</issn><eissn>1468-2494</eissn><abstract>Objectives
This work aimed to design, synthesize and characterize replacement natural moisturizing factor (NMF) composed of modified hygroscopic linear amino acids to pre‐empt or repair skin barrier dysfunction.
Methods
Following synthesis and characterization, thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water binding to the new compounds. Deliquescence relative humidity demonstrated the water‐scavenging ability of the compounds, whereas snake skin moisturizing studies showed they increased water uptake into snake skin.
Results
From thermal analysis, N‐hydroxyglycine showed greatest water‐holding capacity followed by N‐hydroxyserine, l‐homoserine and α‐hydroxyglycine; coupled with quantum mechanics molecular modelling, between 8 and 12 molecules of water could associate with each molecule of either N‐hydroxyglycine, N‐hydroxyserine or l‐homoserine. All of our modified amino acids were efficacious and induced similar or greater water uptake compared with the established moisturizing compounds hyaluronic acid, glycerine and urea in snake skin. Incorporated at 10% in Oilatum, N‐hydroxyserine induced >200% greater moisture uptake into dry snake skin compared to treatment with water alone, with efficacy related to the molecule structure and ability to bind to 12 water molecules. Oilatum cream spiked with all our unnatural amino acid hydrotropes increased water uptake into snake skin compared with Oilatum alone.
The compound series was designed to elucidate some structure – efficacy relationships. Amino acid chirality did not affect the water‐holding capacity but did affect uptake into skin. Compounds with high melting points and bond energies tended to decrease water‐holding capacity. With isosteric replacement, the more electronegative atoms gave greater water‐holding capacities.
Conclusions
This work demonstrates the potential of unnatural amino acid hydrotropes as skin moisturizers and has developed some predictive ‘rules’ for further design and refinement of chemical structures.
Résumé
Objectifs
Ce travail vise à concevoir, synthétiser et 0 caractériser le remplacement du Natural Moisturising Factor (NMF) composé d'acides aminés linéaires hygroscopiques modifiés pour anticiper ou réparer un dysfonctionnement de la barrière cutanée.
Methode
Après la synthèse et la caractérisation, l'analyse thermo‐gravimétrique et la modélisation par la mécanique quantique moléculaire permettent de quantifier et représenter les nouveaux composés liés à l'eau. A humidité relative on démontre la capacité des composés piégeant l'eau, tandis que les études d'hydratation de la peau de serpent ont montré qu'ils ont augmenté l'absorption de l'eau dans la peau de serpent.
Résultats
De l'analyse thermique, la N‐hydroxyglycine a montré la plus grande capacité de rétention d'eau suivie de N‐hydroxyserine, l‐homosérine et α‐hydroxyglycine; couplée avec la modélisation mécanique quantique moléculaire, entre 8 et 12 molécules d'eau pourrait s'associer à chaque molécule de l'une des N‐hydroxyglycine, N‐hydroxyserine ou lL‐homosérine. Tous les acides aminés modifiés sont efficaces et conduisent à une absorbance d'eau similaire ou supérieure par rapport aux composés hydratants établis tels que l'acide hyaluronique, la glycérine et l'urée dans la peau de serpent. Incorporée à 10% dans Oilatum, la N‐hydroxyserine induit une plus grande absorption de l'humidité dans la peau de serpent sèche de 200% par rapport au traitement avec de l'eau seule, avec une efficacité liée à la structure des molécules et la capacité de se lier à 12 molécules d'eau. Une crème Oilatum renforcée avec tous nos hydrotropes d'acides aminés non naturels augmente l'absorption d'eau dans la peau de serpent par rapport à Oilatum seul.
La série des composés a été conçue pour élucider certaines relations structure ‐ efficacité. La chiralité des acides aminés n'a pas affecté la capacité de rétention d'eau, mais a affecté l'absorption dans la peau. Les composés ayant des points de fusion et des énergies de liaison ont tendance à diminuer la capacité de rétention d'eau. Avec le remplacement isostérique, les atomes plus électronégatifs ont donné une plus grande capacité de rétention d'eau.
Conclusions
Ce travail démontre le potentiel des acides aminés non naturels hydrotropes comme hydratants pour la peau et a développé des «règles» de prédiction pour poursuivre la conception et l'amélioration des structures chimiques.
Chemically‐modified linear amino acids, based on the Natural Moisturising Factor constituents glycine and serine, were designed, synthesised and evaluated as moisturisers. Deliquescence relative humidity demonstrated increased water‐scavenging ability of the compounds compared to their parent amino acids whereas thermo‐gravimetric analysis and quantum mechanics molecular modelling quantified and depicted water‐binding to the new hydrotropes. Moisturisation was demonstrated in a snake skin model, and together with results from natural amino acids, structure‐efficacy relationships were developed for the water‐holding abilities of linear amino acid moisturisers.</abstract><cop>England</cop><pub>John Wiley and Sons Inc</pub><pmid>27380298</pmid><doi>10.1111/ics.12351</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0142-5463 |
| ispartof | International journal of cosmetic science, 2017-02, Vol.39 (1), p.72-82 |
| issn | 0142-5463 1468-2494 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_5244679 |
| source | MEDLINE; Access via Wiley Online Library |
| subjects | Amino Acids - chemistry Animals chemical synthesis deliquescence relative humidity delivery Humans hygroscopic Magnetic Resonance Spectroscopy natural moisturizing factor Original Powder Diffraction skin barrier Skin Physiological Phenomena Snakes Spectrophotometry, Infrared Thermogravimetry Water Loss, Insensible |
| title | Design, synthesis and characterization of linear unnatural amino acids for skin moisturization |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-11T15%3A41%3A21IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Design,%20synthesis%20and%20characterization%20of%20linear%20unnatural%20amino%20acids%20for%20skin%20moisturization&rft.jtitle=International%20journal%20of%20cosmetic%20science&rft.au=Arezki,%20N.%20R.&rft.date=2017-02&rft.volume=39&rft.issue=1&rft.spage=72&rft.epage=82&rft.pages=72-82&rft.issn=0142-5463&rft.eissn=1468-2494&rft_id=info:doi/10.1111/ics.12351&rft_dat=%3Cproquest_pubme%3E1826712135%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1826712135&rft_id=info:pmid/27380298&rfr_iscdi=true |