ArticleProceedings of the National Academy of Sciences of the United States of America1996
4-Oxoretinol, a new natural ligand and transactivator of the retinoic acid receptors.
Article in Proceedings of the National Academy of Sciences of the United States of America, 1996. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 113 citations in OpenAlex.
- Nature of back slopping kombucha fermentation process: insights from the microbial succession, metabolites composition changes and their correlations.Frontiers in microbiology · 2024Article
- Retinoid metabolism: new insights.Journal of molecular endocrinology · 2022Review
- Mechanisms of Feedback Regulation of Vitamin A Metabolism.Nutrients · 2022Review
- Anterior patterning genes induced by Zic1 are sensitive to retinoic acid and its metabolite, 4-oxo-RA.Developmental dynamics : an official publication of the American Association of Anatomists · 2022Article
- Altered vitamin A metabolism in human liver slices corresponds to fibrogenesis.Clinical and translational science · 2021Article
- Ethanol promotes differentiation of embryonic stem cells through retinoic acid receptor-γ.The Journal of biological chemistry · 2019Article
- Vitamin A Deficiency and the Lung.Nutrients · 2018Review
- An Assessment of Oxidative Damage and Non-Enzymatic Antioxidants Status Alteration in Relation to Disease Progression in Breast Diseases.Medical sciences (Basel, Switzerland) · 2016Article
- Stereoselective formation and metabolism of 4-hydroxy-retinoic Acid enantiomers by cytochrome p450 enzymes.The Journal of biological chemistry · 2012Article
- UVA/B exposure promotes the biosynthesis of dehydroretinol in cultured human keratinocytes.Molecular and cellular biochemistry · 2012Article
- Retinyl ester hydrolases and their roles in vitamin A homeostasis.Biochimica et biophysica acta · 2012Review
- Retinoids regulate stem cell differentiation.Journal of cellular physiology · 2011Review
- Retinoid pathway and cancer therapeutics.Advanced drug delivery reviews · 2010Review
- From carrot to clinic: an overview of the retinoic acid signaling pathway.Cellular and molecular life sciences : CMLS · 2010Review
- Acidic retinoids synergize with vitamin A to enhance retinol uptake and STRA6, LRAT, and CYP26B1 expression in neonatal lung.Journal of lipid research · 2010Article
- Kidneys of Alb/TGF-beta1 transgenic mice are deficient in retinoic acid and exogenous retinoic acid shows dose-dependent toxicity.Nephron. Experimental nephrology · 2010Article
- Metabolism and regulation of gene expression by 4-oxoretinol versus all-trans retinoic acid in normal human mammary epithelial cells.Journal of cellular physiology · 2009Article
- LIF removal increases CRABPI and CRABPII transcripts in embryonic stem cells cultured in retinol or 4-oxoretinol.Molecular and cellular endocrinology · 2008Article
- Dynamic expression of retinoic acid-synthesizing and -metabolizing enzymes in the developing mouse inner ear.The Journal of comparative neurology · 2006Article
- Metabolism and transactivation activity of 13,14-dihydroretinoic acid.The Journal of biological chemistry · 2005Article
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Authors and funding
11 authors at 1 institution in 1 country.
Funding
Abstract
All-trans-retinoic acid (at-RA) induces cell differentiation in a wide variety of cell types, including F9 embryonic teratocarcinoma cells, and can influence axial pattern formation during embryonic development. We now identify a novel retinoid synthetic pathway in differentiating F9 cells that results in the intracellular production of 4-oxoretinol (4-oxo-ROL) from retinol (vitamin A). Approximately 10-15% of the total retinol in the culture is metabolized to 4-hydroxyretinol and 4-oxo-ROL by the at-RA-treated, differentiating F9 cells over an 18-hr period, but no detectable metabolism of all-trans-retinol to at-RA or 9-cis-retinoic acid is observed in these cells. Remarkably, we show that 4-oxo-ROL can bind and activate transcription of the retinoic acid receptors whereas all-trans-retinol shows neither activity. Low doses of 4-oxo-ROL (e.g., 10(-9) or 10(-10 M) can activate the retinoic acid receptors even though, unlike at-RA, 4-oxo-ROL does not contain an acid moiety at the carbon 15 position. 4-oxo-ROL does not bind or transcriptionally activate the retinoid X receptors. Treatment of F9 cells with 4-oxo-ROL induces differentiation without conversion to the acid and 4-oxo-ROL is active in causing axial truncation when administered to Xenopus embryos at the blastula stage. Thus, 4-oxo-ROL is a natural, biologically active retinoid that is present in differentiated F9 cells. Our data suggest that 4-oxo-ROL may be a novel signaling molecule and regulator of cell differentiation.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.