Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids

The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-I...

Full description

Main Authors: Moshikur, R.M., Chowdhury, M.R., Wakabayashi, R., Tahara, Y., Moniruzzaman, M., Goto, M.
Format: Article
Institution: Universiti Teknologi Petronas
Record Id / ISBN-0: utp-eprints.21449 /
Published: Elsevier B.V. 2018
Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85047271527&doi=10.1016%2fj.ijpharm.2018.05.021&partnerID=40&md5=e6b2e5435aa4949bbb4ffa718024e2bd
http://eprints.utp.edu.my/21449/
Tags: Add Tag
No Tags, Be the first to tag this record!
id utp-eprints.21449
recordtype eprints
spelling utp-eprints.214492018-09-25T06:33:47Z Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids Moshikur, R.M. Chowdhury, M.R. Wakabayashi, R. Tahara, Y. Moniruzzaman, M. Goto, M. The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs. © 2018 Elsevier B.V. Elsevier B.V. 2018 Article NonPeerReviewed https://www.scopus.com/inward/record.uri?eid=2-s2.0-85047271527&doi=10.1016%2fj.ijpharm.2018.05.021&partnerID=40&md5=e6b2e5435aa4949bbb4ffa718024e2bd Moshikur, R.M. and Chowdhury, M.R. and Wakabayashi, R. and Tahara, Y. and Moniruzzaman, M. and Goto, M. (2018) Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids. International Journal of Pharmaceutics, 546 (1-2). pp. 31-38. http://eprints.utp.edu.my/21449/
institution Universiti Teknologi Petronas
collection UTP Institutional Repository
description The technological utility of active pharmaceutical ingredients (APIs) is greatly enhanced when they are transformed into ionic liquids (ILs). API-ILs have better solubility, thermal stability, and the efficacy in topical delivery than solid or crystalline drugs. However, toxicological issue of API-ILs is the main challenge for their application in drug delivery. To address this issue, 11 amino acid esters (AAEs) were synthesized and investigated as biocompatible counter cations for the poorly water-soluble drug salicylic acid (Sal) to form Sal-ILs. The AAEs were characterized using 1H and 13C NMR, FTIR, elemental, and thermogravimetric analyses. The cytotoxicities of the AAE cations, Sal-ILs, and free Sal were investigated using mammalian cell lines (L929 and HeLa). The toxicities of the AAE cations greatly increased with inclusion of long alkyl chains, sulfur, and aromatic rings in the side groups of the cations. Ethyl esters of alanine, aspartic acid, and proline were selected as a low cytotoxic AAE. The cytotoxicities of the Sal-ILs drastically increased compared with the AAEs on incorporation of Sal into the cations, and were comparable to that of free Sal. Interestingly, the water miscibilities of the Sal-ILs were higher than that of free Sal, and the Sal-ILs were miscible with water at any ratio. A skin permeation study showed that the Sal-ILs penetrated through skin faster than the Sal sodium salt. These results suggest that AAEs could be used in biomedical applications to eliminate the use of traditional toxic solvents for transdermal delivery of poorly water-soluble drugs. © 2018 Elsevier B.V.
format Article
author Moshikur, R.M.
Chowdhury, M.R.
Wakabayashi, R.
Tahara, Y.
Moniruzzaman, M.
Goto, M.
spellingShingle Moshikur, R.M.
Chowdhury, M.R.
Wakabayashi, R.
Tahara, Y.
Moniruzzaman, M.
Goto, M.
Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
author_sort Moshikur, R.M.
title Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
title_short Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
title_full Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
title_fullStr Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
title_full_unstemmed Characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
title_sort characterization and cytotoxicity evaluation of biocompatible amino acid esters used to convert salicylic acid into ionic liquids
publisher Elsevier B.V.
publishDate 2018
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85047271527&doi=10.1016%2fj.ijpharm.2018.05.021&partnerID=40&md5=e6b2e5435aa4949bbb4ffa718024e2bd
http://eprints.utp.edu.my/21449/
_version_ 1741196461393051648
score 11.62408

Similar Items