Bisphenolic compounds that enhance cell cation transport are found in commercial phenol red

Journal of Medicinal Chemistry
P R KymJ A Katzenellenbogen

Abstract

We have isolated two bisphenolic compounds (4 and 5) that have a marked effect on K+ and Na+ concentrations in human cells from commercial preparations of the pH indicator dye phenol red (phenolsulfonphthalein). We used a bioassay to identify active chromatographic fractions from the lipophilic impurities present in phenol red, and we determined the structure of two active components (4 and 5) by 1H and 13C NMR and mass spectrometry. When added to human fibroblasts in serum-free medium, the bisphenol fluorene derivative 9,9-bis(4'-hydroxyphenyl)-3-hydroxyfluorene (5) produced a rapid loss of K+ and a gain of Na+, at low concentrations, with an EC50 between 30 and 60 ng/mL (80-160 nM). The 2- and 4-hydroxy isomers of the fluorene 5 (i.e., compounds 6 and 7), prepared by synthesis, had similar activity, although compound 6 was somewhat less potent. The bisphenol xanthene derivative 9,9-bis(4'-hydroxyphenyl)xanthene (4) elicited a similar biological response but was less potent than 5-7; it also had a strong effect on cell adhesion, causing release of cells from the plastic substrate at concentrations as low as 2-5 microg/mL (5.5-14 microM). The structures of xanthene (4) and fluorene (5) bisphenols have been confirmed by synthesi...Continue Reading

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Citations

Aug 28, 2003·Clinical and Experimental Pharmacology & Physiology·Robert W MasonLaszlo Hopp
Mar 22, 2005·British Journal of Pharmacology·Brian F KingGeoffrey Burnstock
Jul 6, 2015·European Journal of Medicinal Chemistry·Aurélien CholletMichel Baltas
Mar 15, 2006·Bioorganic & Medicinal Chemistry Letters·Thomas A SpencerChristopher J Fielding
Feb 9, 2008·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Katie ShorterValerie A Randall

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