Design, synthesis and P-gp induction activity of aryl phosphonate esters: identification of tetraethyl-2-phenylethene-1,1-diyldiphosphonate as an orally bioavailable P-gp inducer

MedChemComm
2016.0

Abstract

The clearance of amyloid-beta is mediated by P-glycoprotein (P-gp) transporter pump located at the blood brain barrier. Therefore, the induction of P-gp has been considered as a potential therapeutic strategy for treatment of Alzheimer's disease. The expression of P-gp is regulated through a nuclear receptor - pregnane-X-receptor (PXR). Thus, herein we investigated the potential of a known pregnane-X-receptor (PXR) activator diphosphonate ester SR12813 (6a) for P-gp induction activity and further studied its structure-activity relationship. A diphosphonate ester SR12813 along with a three series of analogs viz. aryl alkylidene, aryl alkynyl, and aryl α-amino phosphonate esters were synthesized and screened for P-gp induction activity in P-gp overexpressing adenocarcinoma LS180 cells using rhodamine-123 efflux assay. The parent compound SR12813 along with several new analogs displayed P-gp induction activity at 5 µM. The western-blot analysis indicated that tetraethyl-2 phenylethene-1,1-diyldiphosphonate (6c) and tetraethyl-2-(anthracene-10-yl)ethene-1,1-diyldiphosphonate (6s) showed 7-8 fold increase in P-gp expression in LS180 cells. The diphosphonate ester 6c displayed excellent aqueous solubility, no cytochrome P450 inhibition liability and no efflux pump substrate liability. Furthermore, it possesses excellent oral pharmacokinetic profile in BALB/c mice with AUC0-∞ of 2067 ng·h/mL and 37.6% oral bioavailability. The results presented here clearly indicate the potential of this scaffold to increase the clearance of brain Aβ across the BBB and thus its promise for development as potential anti-Alzheimer agents.

Knowledge Graph

Similar Paper

Design, synthesis and P-gp induction activity of aryl phosphonate esters: identification of tetraethyl-2-phenylethene-1,1-diyldiphosphonate as an orally bioavailable P-gp inducer
MedChemComm 2016.0
Functional induction of P-glycoprotein efflux pump by phenyl benzenesulfonamides: Synthesis and biological evaluation of T0901317 analogs
European Journal of Medicinal Chemistry 2016.0
Discovery of a marine-derived bis-indole alkaloid fascaplysin, as a new class of potent P-glycoprotein inducer and establishment of its structure–activity relationship
European Journal of Medicinal Chemistry 2016.0
Brain penetrant liver X receptor (LXR) modulators based on a 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole core
Bioorganic & Medicinal Chemistry Letters 2016.0
SAR study on arylmethyloxyphenyl scaffold: Looking for a P-gp nanomolar affinity
European Journal of Medicinal Chemistry 2014.0
Structure−Activity Relationships Studies in a Series of N,N-Bis(alkanol)amine Aryl Esters as P-Glycoprotein (Pgp) Dependent Multidrug Resistance (MDR) Inhibitors
Journal of Medicinal Chemistry 2010.0
Novel Insight in Structure−Activity Relationship and Bioanalysis of P-Glycoprotein Targeting Highly Potent Tetrakishydroxymethyl Substituted 3,9-Diazatetraasteranes
Journal of Medicinal Chemistry 2008.0
Modulation of the spacer in N,N-bis(alkanol)amine aryl ester heterodimers led to the discovery of a series of highly potent P-glycoprotein-based multidrug resistance (MDR) modulators
European Journal of Medicinal Chemistry 2019.0
Synthesis and evaluation of dihydropyrimidinone-derived selenoesters as multi-targeted directed compounds against Alzheimer’s disease
Bioorganic & Medicinal Chemistry 2016.0
Design, synthesis and biological evaluation of stereo- and regioisomers of amino aryl esters as multidrug resistance (MDR) reversers
European Journal of Medicinal Chemistry 2019.0