Search results for "Retinoic Acid"
showing 10 items of 107 documents
Retinoid dynamics in chicken eye during pre- and postnatal development.
1994
Changes in the steady state level of retinols, retinaldehydes and retinyl esters in the trans and 11-cis forms and trans retinoic acid were measured in whole chicken eye during development from day 6 in ovo to day 3 post-hatch. These retinoids, quantified by different HPLC systems, were detected in this time sequence: trans-retinol and trans-retinyl esters in the first week in ovo, 11-cis-retinol in the second week. The highest level of 11-cis-retinaldehyde and 11-cis-retinyl esters was reached at the end of development in ovo; however, their levels increased further after hatching. The retinoic acid level decreased at the end of the first week, rising again at the end of the second week. T…
Retinoic Acid and the Gut Microbiota in Alzheimer’s Disease: Fighting Back-to-Back?
2019
Background:There is growing evidence that the gut microbiota may play an important role in neurodegenerative diseases such as Alzheimer’s disease. However, how these commensals influence disease risk and progression still has to be deciphered.Objective:The objective of this review was to summarize current knowledge on the interplay between gut microbiota and retinoic acid. The latter one represents one of the important micronutrients, which have been correlated to Alzheimer’s disease and are used in initial therapeutic intervention studies.Methods:A selective overview of the literature is given with the focus on the function of retinoic acid in the healthy and diseased brain, its metabolism…
Trienediolates of hexadienoic acids in synthesis. synthesis of retinoic and nor-retinoic acids.
1993
Abstract Double deprotonation of either (E,E)-3-methyl-2,4-hexadienoic acid 2, or 4,6-dimethyldihydro-2-pyrone 3 generates apparently the same lithium trienediolate, which affords ω-hydroxy acids 9 on reaction with ketones 7. Hydroxy acids 9 are easily dehydrated to octatrienoic acids 5, which are structurally related to retinoic acid. Similarly, sorbic acid 1 leads to nor-retinoic acid analogs 6.
Convenient Synthesis of Biologically Important Retinoids
1995
The toxic and teratogenic effects caused by the highly biologically active (all-E)-retinoic acid and its derivatives prompted us to synthesize a number of retinoids. We developed synthetic approaches to (all-E)-retinyl β-D-glucuronide 3, methyl (retinoyl β-D-glucopyranoside)uronate 5, (all-E)-retinoic acid β-D-glucopyranosyl ester 8 and (all-E)-retinoyl β-D-glucuronide 6 in high purity and yield. Compound 3 was synthesized under Koenigs-Knorr conditions from (all-E)-retinol and an α-halogenose. Compounds 5 and 8 were prepared by esterification of a silver salt of (all-E)-retinoic acid with an α-glycosyl halide in pyridine. (all-E)-Retinoyl β-D-glucuronide 6 was prepared by reaction of (all-…
ChemInform Abstract: Trienediolates of Hexadienoic Acids in Synthesis. Synthesis of Retinoic and nor-Retinoic Acids.
2010
Abstract Double deprotonation of either (E,E)-3-methyl-2,4-hexadienoic acid 2, or 4,6-dimethyldihydro-2-pyrone 3 generates apparently the same lithium trienediolate, which affords ω-hydroxy acids 9 on reaction with ketones 7. Hydroxy acids 9 are easily dehydrated to octatrienoic acids 5, which are structurally related to retinoic acid. Similarly, sorbic acid 1 leads to nor-retinoic acid analogs 6.
Retinoid acid and analogs as potent inducers of differentiation and apoptosis. New promising chemopreventive and chemotherapeutic agents in oncology
2001
Abstract In this report we will describe the preparation and the biological activity of a novel class of heterocyclic arotinoids endowed with potent cytotoxic and apoptotic acitivity. Structureactivity relationship studies revealed that the different stereochemistry at the C9 double bond of retinoids seems associated with a different biological activity: potent apoptotic activity for the cis-isomers, whereas differentiating activity for the trans structures. An interesting modified Wittig procedure that allows easily to arotinoids will also be described. The substitution of the alkenyl portion with a more flexible oxymethyl or aminomethyl moiety gave compounds with poor activity, whereas i…
Effect of cytochrome P450 inhibitors (diethyl dithiocarbamate, ketoconazole and grapefruit juice) on the pharmacokinetics of all-trans-retinoic acid.
2004
Diethyl dithiocarbamate (DEDTC) has been reported to be a more powerful inhibitor of all-trans-retinoic acid (ATRA) in vitro metabolism than the well-established cytochrome P450 (CYP) inhibitor ketoconazole (KC). In recent years grapefruit juice (GJ) has been shown to be able to increase the oral bioavailability of several drugs by inhibiting intestinal CYP. This study investigated the in vivo effect of these CYP inhibitors on the pharmacokinetics of ATRA. The latter was administered to rats as a constant-rate intravenous (i.v.) infusion (0.48 mg h(-1) kg(-1)) during 10 h and orally (1.6 mg kg(-1)). DEDTC (320 mg kg(-1) x 2 i.v., 6.4 and 32 mg kg(-1) per os (p.o.)) did not change the ATRA c…
Regulation of the activity of the Cholesteryl Ester Tranfer Protein (CETP) : electrostatics interactions with carboxylic derivatives (Non Esterified …
1997
In human plasma, the cholesteryl ester transfer protein (CETP) plays a key role in lipoprotein metabolism by promoting the net mass transfer of cholesteryl esters from HDL towards apoB-containing lipoproteins, and the transfer of triglycerides from VLDL towards HDL and LDL. Thus CETP arises as a potentially important factor in plasma lipoproteins metabolism, a statement which raised a considerable interest in identifying the factors which may regulate CETP activity.In our in vitro studies, we demonstrated that amphipathic molecules (non esterified fatty acids and retinoic acids) constituted of one carboxylic head group and one hydrophobic carbon chain are able to increase the cholesteryl es…
Discovery of Retinoic Acid-Related Orphan Receptor γt Inverse Agonists via Docking and Negative Image-Based Screening
2018
Retinoic acid-related orphan receptor γt (RORγt) has a vital role in the differentiation of T-helper 17 (TH17) cells. Potent and specific RORγt inverse agonists are sought for treating TH17-related diseases such as psoriasis, rheumatoid arthritis, and type 1 diabetes. Here, the aim was to discover novel RORγt ligands using both standard molecular docking and negative image-based screening. Interestingly, both of these in silico techniques put forward mostly the same compounds for experimental testing. In total, 11 of the 34 molecules purchased for testing were verified as RORγt inverse agonists, thus making the effective hit rate 32%. The pIC50 values for the compounds varied from 4.9 (11 μ…
Uniform response of c-raf expression to differentiation induction and inhibition of proliferation in a rat rhabdomyosarcoma cell line
1990
The clonal rat rhabdomyosarcoma cell line BA-HAN-1C is composed of proliferating mononuclear cells, some of which spontaneously fuse to terminally differentiated myotube-like giant cells. Both the induction of differentiation by retinoic acid (RA) and by sodium butyrate (NaBut), as well as the inhibition of proliferation by fetal calf serum (FCS)-depleted medium uniformly resulted in the same effects. There was a significant (p less than 0.001) inhibition of proliferation and induction of cellular differentiation, as evidenced by a significant (p less than 0.05) increase in creatine kinase activity. Furthermore, after exposure to RA-supplemented or FCS-depleted medium, a significant (p less…