| Bisphenols that stimulate cells to release alkali metal cations: a structure-activity study. | |
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MedLine Citation:
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PMID: 9784117 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The laxative action of phenolphthalein (5) is believed to result from induction of potassium and water efflux from the colon epithelium. In cultured cells, K+ efflux is promoted by 5 and by a contaminant (1) present in commercial phenol red. Six compounds with chemical structures related to those of 5 and 1 were tested for ability to induce the release of 86Rb from COS-7 cells preloaded with this isotope: 4,4'-(9-fluorenylidene)diphenol (2), 4, 4'-(9-fluorenylidene)dianiline, 4, 4'-(9-fluorenylidene)bisphenoxyethanol, 1,1'-bi-2-naphthol, 4, 4'-biphenol, and bis(4-hydroxyphenyl)methane. With one exception these compounds were all inactive at a concentration of 10 microM. However, 2 caused profound 86Rb efflux at concentrations as low as 100 nM. Concentrations of 5 1-2 orders of magnitude higher were needed to achieve similar levels of activity. The three compounds known to be active in this experimental system share a common feature that is absent in all the inactive compounds: a five-membered ring structure, one of whose carbon atoms is disubstituted with p-hydroxyphenyl residues. Because 2 and 5 are readily available, comparative studies on the mechanism of action of these biphenols at the cellular level can now be undertaken. |
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Authors:
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L Hopp; S O Megee; J B Lloyd |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of medicinal chemistry Volume: 41 ISSN: 0022-2623 ISO Abbreviation: J. Med. Chem. Publication Date: 1998 Oct |
Date Detail:
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Created Date: 1998-11-23 Completed Date: 1998-11-23 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9716531 Medline TA: J Med Chem Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 4421-3 Citation Subset: IM |
Affiliation:
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Department of Pediatrics, Jefferson Medical College, Alfred I. duPont Hospital for Children, Wilmington, Delaware 19803, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals COS Cells Cathartics / chemistry, pharmacology* Cations, Monovalent / metabolism* Metals, Alkali / metabolism* Phenolphthaleins / chemistry, pharmacology* Phenolsulfonphthalein / chemistry, pharmacology* Rubidium Radioisotopes / metabolism Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Cathartics; 0/Cations, Monovalent; 0/Metals, Alkali; 0/Phenolphthaleins; 0/Rubidium Radioisotopes; 143-74-8/Phenolsulfonphthalein |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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