Data on biosynthesis of BPAF glucuronide, enzyme kinetics of BPAF glucuronidation, and molecular modeling

Darja Gramec Skledar; Jurij Trontelj; Johanna Troberg; Tihomir Tomašič; Anamarija Zega; Moshe Finel; Lucija Peterlin Mašič

doi:10.1016/j.dib.2018.12.033

Data on biosynthesis of BPAF glucuronide, enzyme kinetics of BPAF glucuronidation, and molecular modeling

Data Brief. 2018 Dec 17:22:977-986. doi: 10.1016/j.dib.2018.12.033. eCollection 2019 Feb.

Authors

Darja Gramec Skledar¹, Jurij Trontelj¹, Johanna Troberg², Tihomir Tomašič¹, Anamarija Zega¹, Moshe Finel², Lucija Peterlin Mašič¹

Affiliations

¹ Faculty of Pharmacy, Aškerčeva 7, 1000 Ljubljana, Slovenia.
² Division of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Helsinki, Helsinki, Finland.

Abstract

Bisphenol AF (BPAF) is in the body mainly metabolized to the corresponding bisphenol AF glucuronide (BPAF-G). While BPAF-G is not commercially available, enzyme-assisted synthesis of BPAF-G using the human recombinant enzyme UGT2A1, purification of BPAF-G by solid phase extraction and semi-preparative HPLC and chemical characterization of BPAF-G by NMR and LC-MS/MS were performed and are described here. Furthermore, BPAF glucuronidation kinetics with the UGT enzymes that showed the highest glucuronidation activity in previous studies (i.e hepatic UGTs 1A3, 2B7, and 2B17, intestinal UGT 1A10 and UGT 2A1 that is present in airways) was performed and data is presented. Hepatic enzymes exhibited high affinities toward BPAF, while extrahepatic UGTs 2A1 and 1A10 showed the high v_max values (3.3 and 3.0 nmol/min/mg, respectively). To understand molecular interactions of BPA, BPAF and BPAF-G with ligand biding sites of several nuclear receptors, molecular modeling was performed and data on the binding modes of BPAF, BPA, and BPAF-G in the ligand-binding sites of nuclear receptors are presented. This article is related to "Endocrine activities and adipogenic effects of bisphenol AF and its main metabolite" (Skledar et al., 2019).