Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology
Azelaic acid (AzA) and its derivatives have been known to be effective in the treatment of acne and various cutaneous hyperpigmentary disorders. The esterification of azelaic acid with lauryl alcohol (LA) to produce dilaurylazelate using immobilized lipase B from Candida antarctica (Novozym 435) is...
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MDPI AG
2018-02-01
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| Series: | Molecules |
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| author | Nurshafira Khairudin Mahiran Basri Hamid Reza Fard Masoumi Shazwani Samson Siti Efliza Ashari |
| author_facet | Nurshafira Khairudin Mahiran Basri Hamid Reza Fard Masoumi Shazwani Samson Siti Efliza Ashari |
| author_sort | Nurshafira Khairudin |
| collection | DOAJ |
| description | Azelaic acid (AzA) and its derivatives have been known to be effective in the treatment of acne and various cutaneous hyperpigmentary disorders. The esterification of azelaic acid with lauryl alcohol (LA) to produce dilaurylazelate using immobilized lipase B from Candida antarctica (Novozym 435) is reported. Response surface methodology was selected to optimize the reaction conditions. A well-fitting quadratic polynomial regression model for the acid conversion was established with regards to several parameters, including reaction time and temperature, enzyme amount, and substrate molar ratios. The regression equation obtained by the central composite design of RSM predicted that the optimal reaction conditions included a reaction time of 360 min, 0.14 g of enzyme, a reaction temperature of 46 °C, and a molar ratio of substrates of 1:4.1. The results from the model were in good agreement with the experimental data and were within the experimental range (R2 of 0.9732).The inhibition zone can be seen at dilaurylazelate ester with diameter 9.0±0.1 mm activities against Staphylococcus epidermidis S273. The normal fibroblasts cell line (3T3) was used to assess the cytotoxicity activity of AzA and AzA derivative, which is dilaurylazelate ester. The comparison of the IC50 (50% inhibition of cell viability) value for AzA and AzA derivative was demonstrated. The IC50 value for AzA was 85.28 μg/mL, whereas the IC50 value for AzA derivative was more than 100 μg/mL. The 3T3 cell was still able to survive without any sign of toxicity from the AzA derivative; thus, it was proven to be non-toxic in this MTT assay when compared with AzA. |
| first_indexed | 2024-12-19T16:39:03Z |
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| last_indexed | 2024-12-19T16:39:03Z |
| publishDate | 2018-02-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj.art-02759a3ffef2475a9175b716752dba402022-12-21T20:13:51ZengMDPI AGMolecules1420-30492018-02-0123239710.3390/molecules23020397molecules23020397Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface MethodologyNurshafira Khairudin0Mahiran Basri1Hamid Reza Fard Masoumi2Shazwani Samson3Siti Efliza Ashari4Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang 43400, Selangor, MalaysiaDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang 43400, Selangor, MalaysiaDepartment of Biomaterials, Iran Polymer and Petrochemical Institute, Tehran 14977-13115, IranDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang 43400, Selangor, MalaysiaDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang 43400, Selangor, MalaysiaAzelaic acid (AzA) and its derivatives have been known to be effective in the treatment of acne and various cutaneous hyperpigmentary disorders. The esterification of azelaic acid with lauryl alcohol (LA) to produce dilaurylazelate using immobilized lipase B from Candida antarctica (Novozym 435) is reported. Response surface methodology was selected to optimize the reaction conditions. A well-fitting quadratic polynomial regression model for the acid conversion was established with regards to several parameters, including reaction time and temperature, enzyme amount, and substrate molar ratios. The regression equation obtained by the central composite design of RSM predicted that the optimal reaction conditions included a reaction time of 360 min, 0.14 g of enzyme, a reaction temperature of 46 °C, and a molar ratio of substrates of 1:4.1. The results from the model were in good agreement with the experimental data and were within the experimental range (R2 of 0.9732).The inhibition zone can be seen at dilaurylazelate ester with diameter 9.0±0.1 mm activities against Staphylococcus epidermidis S273. The normal fibroblasts cell line (3T3) was used to assess the cytotoxicity activity of AzA and AzA derivative, which is dilaurylazelate ester. The comparison of the IC50 (50% inhibition of cell viability) value for AzA and AzA derivative was demonstrated. The IC50 value for AzA was 85.28 μg/mL, whereas the IC50 value for AzA derivative was more than 100 μg/mL. The 3T3 cell was still able to survive without any sign of toxicity from the AzA derivative; thus, it was proven to be non-toxic in this MTT assay when compared with AzA.http://www.mdpi.com/1420-3049/23/2/397azelaic acidanti-acneenzymatic reactionNovozym 435response surface methodology (RSM) |
| spellingShingle | Nurshafira Khairudin Mahiran Basri Hamid Reza Fard Masoumi Shazwani Samson Siti Efliza Ashari Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology Molecules azelaic acid anti-acne enzymatic reaction Novozym 435 response surface methodology (RSM) |
| title | Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology |
| title_full | Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology |
| title_fullStr | Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology |
| title_full_unstemmed | Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology |
| title_short | Enhancing the Bioconversion of Azelaic Acid to Its Derivatives by Response Surface Methodology |
| title_sort | enhancing the bioconversion of azelaic acid to its derivatives by response surface methodology |
| topic | azelaic acid anti-acne enzymatic reaction Novozym 435 response surface methodology (RSM) |
| url | http://www.mdpi.com/1420-3049/23/2/397 |
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