Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity

Ksenija Pavlović; Ljubica Grbović; Milica Karadžić Banjac; Strahinja  Kovačević; Anamarija Mandić; Sanja Podunavac-Kuzmanović; Bojana Vasiljević

doi:10.20450/mjcce.2023.2707

Authors

Ksenija Pavlović Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, Novi Sad, Serbia https://orcid.org/0000-0001-6339-1350
Ljubica Grbović Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences,University of Novi Sad, Trg DositejaObradovića 3, Novi Sad, Serbia
Milica Karadžić Banjac Faculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, Serbia https://orcid.org/0000-0002-0514-4033
Strahinja Kovačević Faculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, Serbia https://orcid.org/0000-0002-5619-9894
Anamarija Mandić University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, Serbia https://orcid.org/0000-0002-5492-7237
Sanja Podunavac-Kuzmanović Faculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, Serbia https://orcid.org/0000-0002-4269-9206
Bojana Vasiljević University of Belgrade, Mike Petrovića Alasa 12-14, Vinča, Serbia https://orcid.org/0000-0002-0335-1987

DOI:

https://doi.org/10.20450/mjcce.2023.2707

Keywords:

chenodeoxycholic acid esters, diols, lipophilicity, liquid chromatography, microwaves

Abstract

In this study, eco-friendly microwave-assisted esterification reactions of chenodeoxycholic acid with medium-chain diols (1,2-ethanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, and 1,10-decanediol) or tetraethylene glycol were accomplished. The synthesized bile acid esters were obtained with high yields (up to 81 %) and purity in a short reaction time (15 min). It is shown that the microwave technique is a suitable method for the preparation of chenodeoxycholic acid esters. In order to obtain detailed insight into the lipophilic behavior of the studied chenodeoxycholic acid esters, a comparative study of chromatographic behavior and lipophilicity was performed. Also, the present study deals with the estimation of pH – logD profiles in order to get an overview of the changes in lipophilicity related to the pH value changes. The obtained results indicate that studied compounds have logD values in the range acceptable for potential drug candidates. Chromatographic lipophilicity of synthesized chenodeoxycholic acid esters successfully correlate with in silico lipophilicity descriptors.

Author Biographies

Anamarija Mandić, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, Serbia

Institute of Food Technology

Bojana Vasiljević, University of Belgrade, Mike Petrovića Alasa 12-14, Vinča, Serbia

Vinča Institute of Nuclear Sciences

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Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity

Authors

DOI:

Keywords:

Abstract

Author Biographies

Anamarija Mandić, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, Serbia

Bojana Vasiljević, University of Belgrade, Mike Petrovića Alasa 12-14, Vinča, Serbia

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