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Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study
1Department of Pediatrics, Jefferson Medical College, Alfred I. duPont Hospital for Children, Wilmington, Delaware 19803, USA.
Journal of Medicinal Chemistry
|October 23, 1998
Summary
Phenolphthalein and a related compound, 4,4'-(9-fluorenylidene)diphenol, induce potassium and water efflux from colon cells. Compound 2 is significantly more potent than phenolphthalein in this cellular efflux assay.
Area of Science:
- Pharmacology
- Cell Biology
- Gastroenterology
Background:
- The laxative effect of phenolphthalein is linked to potassium and water efflux from colon epithelium.
- A contaminant in phenol red also promotes potassium efflux in cultured cells.
Purpose of the Study:
- To investigate the chemical structures responsible for inducing ion and water efflux.
- To compare the potency of phenolphthalein and related compounds in a cellular efflux model.
Main Methods:
- Tested six structurally related compounds for their ability to induce 86Rubidium efflux from COS-7 cells.
- Utilized a quantitative isotope efflux assay to measure cellular ion release.
Main Results:
- 4,4'-(9-fluorenylidene)diphenol (2) induced significant 86Rubidium efflux at 100 nM, outperforming phenolphthalein (5).
- Phenolphthalein required 1-2 orders of magnitude higher concentrations for similar activity.
- Active compounds share a common structural feature: a five-membered ring with disubstituted p-hydroxyphenyl residues.
Conclusions:
- The structural motif of a five-membered ring with specific substitutions is crucial for inducing ion efflux.
- Compound 2 is a highly potent inducer of ion efflux, offering a valuable tool for mechanistic studies.
- Further comparative studies on the cellular mechanisms of these biphenols are warranted.