Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) introduced in the 1960s and widely used as an analgesic, anti-inflammatory, and antipyretic. In its acid form, the solubility of 21 mg/L greatly limits its bioavailability. Since the bioavailability of a drug product plays a critical role in...
Main Authors: | , , , , , |
---|---|
Format: | Article |
Language: | English |
Published: |
MDPI AG
2021-03-01
|
Series: | International Journal of Molecular Sciences |
Subjects: | |
Online Access: | https://www.mdpi.com/1422-0067/22/6/3066 |
id |
doaj-aea344ecb8374993b94819642c1ece24 |
---|---|
record_format |
Article |
spelling |
doaj-aea344ecb8374993b94819642c1ece242021-03-18T00:02:21ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-03-01223066306610.3390/ijms22063066Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic MediaFederico Zappaterra0Maria Elena Maldonado Rodriguez1Daniela Summa2Bruno Semeraro3Stefania Costa4Elena Tamburini5Department of Life Sciences and Biotechnology, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Biotechnology Engineering of the RRNN, Salesian Polytechnic University, Av. 12 de Octubre y Wilson, Quito 170109, EcuadorDepartment of Life Sciences and Biotechnology, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyGATE SRL, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Life Sciences and Biotechnology, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Life Sciences and Biotechnology, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyIbuprofen is a nonsteroidal anti-inflammatory drug (NSAID) introduced in the 1960s and widely used as an analgesic, anti-inflammatory, and antipyretic. In its acid form, the solubility of 21 mg/L greatly limits its bioavailability. Since the bioavailability of a drug product plays a critical role in the design of oral administration dosage, this study investigated the enzymatic esterification of ibuprofen as a strategy for hydrophilization. This work proposes an enzymatic strategy for the covalent attack of highly hydrophilic molecules using acidic functions of commercially available bioactive compounds. The poorly water-soluble drug ibuprofen was esterified in a hexane/water biphasic system by direct esterification with sorbitol using the cheap biocatalyst porcine pancreas lipase (PPL), which demonstrated itself to be a suitable enzyme for the effective production of the IBU-sorbitol ester. This work reports the optimization of the esterification reaction.https://www.mdpi.com/1422-0067/22/6/3066ibuprofensorbitolesterificationporcine pancreas lipaseprodrug |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Federico Zappaterra Maria Elena Maldonado Rodriguez Daniela Summa Bruno Semeraro Stefania Costa Elena Tamburini |
spellingShingle |
Federico Zappaterra Maria Elena Maldonado Rodriguez Daniela Summa Bruno Semeraro Stefania Costa Elena Tamburini Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media International Journal of Molecular Sciences ibuprofen sorbitol esterification porcine pancreas lipase prodrug |
author_facet |
Federico Zappaterra Maria Elena Maldonado Rodriguez Daniela Summa Bruno Semeraro Stefania Costa Elena Tamburini |
author_sort |
Federico Zappaterra |
title |
Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media |
title_short |
Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media |
title_full |
Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media |
title_fullStr |
Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media |
title_full_unstemmed |
Biocatalytic Approach for Direct Esterification of Ibuprofen with Sorbitol in Biphasic Media |
title_sort |
biocatalytic approach for direct esterification of ibuprofen with sorbitol in biphasic media |
publisher |
MDPI AG |
series |
International Journal of Molecular Sciences |
issn |
1661-6596 1422-0067 |
publishDate |
2021-03-01 |
description |
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) introduced in the 1960s and widely used as an analgesic, anti-inflammatory, and antipyretic. In its acid form, the solubility of 21 mg/L greatly limits its bioavailability. Since the bioavailability of a drug product plays a critical role in the design of oral administration dosage, this study investigated the enzymatic esterification of ibuprofen as a strategy for hydrophilization. This work proposes an enzymatic strategy for the covalent attack of highly hydrophilic molecules using acidic functions of commercially available bioactive compounds. The poorly water-soluble drug ibuprofen was esterified in a hexane/water biphasic system by direct esterification with sorbitol using the cheap biocatalyst porcine pancreas lipase (PPL), which demonstrated itself to be a suitable enzyme for the effective production of the IBU-sorbitol ester. This work reports the optimization of the esterification reaction. |
topic |
ibuprofen sorbitol esterification porcine pancreas lipase prodrug |
url |
https://www.mdpi.com/1422-0067/22/6/3066 |
work_keys_str_mv |
AT federicozappaterra biocatalyticapproachfordirectesterificationofibuprofenwithsorbitolinbiphasicmedia AT mariaelenamaldonadorodriguez biocatalyticapproachfordirectesterificationofibuprofenwithsorbitolinbiphasicmedia AT danielasumma biocatalyticapproachfordirectesterificationofibuprofenwithsorbitolinbiphasicmedia AT brunosemeraro biocatalyticapproachfordirectesterificationofibuprofenwithsorbitolinbiphasicmedia AT stefaniacosta biocatalyticapproachfordirectesterificationofibuprofenwithsorbitolinbiphasicmedia AT elenatamburini biocatalyticapproachfordirectesterificationofibuprofenwithsorbitolinbiphasicmedia |
_version_ |
1724218021653774336 |