1184-20-9Relevant academic research and scientific papers
Novel 3,4-seco bile acid diamides as selective anticancer proliferation and migration agents
Mao, Shi-Wei,Chen, Huang,Yu, Li-Fang,Lv, Fang,Xing, Ya-Jing,Liu, Ting,Xie, Jia,Tang, Jie,Yi, Zhengfang,Yang, Fan
, p. 574 - 583 (2016)
A series of new seco-A ring bile acid diamides were synthesized, and their antiproliferative activities against PC3M (prostate), HT29 (colon) and ES-2 (ovarian) cancer cell lines were investigated using SRB assays. Most synthesized compounds presented improved antiproliferative activities compared to the parent bile acids (IC50> 80 μM), especially the piperazine conjugated compound 27 with IC50values of 1.07, 4.58 and 3.86 μM against PC3M, HT29 and ES-2 cancer cell lines, respectively. In addition, all the tested compounds showed less cytotoxic activity on a noncancerous cell line (HAF), and the most active compound 27 exhibited the highest selectivity (Selectivity Index, SIPC3M= 26.3). Furthermore, 27 could also enhance G1 arrest in PC3M cell, revealed by cell cycle analysis, and increase anti-migration activity on PC3M cells, confirmed by transwell migration assay.
Synthesis and biological activity of cyclopropyl Δ7-dafachronic acids as DAF-12 receptor ligands
Carotti, Andrea,Ceccarelli, Giada,Gioiello, Antimo,Goracci, Laura,Mancino, Valentina,Passeri, Daniela,Pellicciari, Roberto,Sardella, Roccaldo
, p. 5403 - 5412 (2021)
The four cyclopropyl stereoisomers of Δ7-dafachronic acids were prepared from the bile acid hyodeoxycholic acid and employed as chemical tools to exploit the importance of the orientation and spatial disposition of the carboxyl tail and the C25-methyl gro
Chemical synthesis of the 3-sulfooxy-7-N-acetylglucosaminyl-24-amidated conjugates of 3β,7β-dihydroxy-5-cholen-24-oic acid, and related compounds: Unusual, major metabolites of bile acid in a patient with Niemann-Pick disease type C1
Iida, Takashi,Kakiyama, Genta,Hibiya, Yohei,Miyata, Shohei,Inoue, Takehiko,Ohno, Kohsaku,Goto, Takaaki,Mano, Nariyasu,Goto, Junichi,Nambara, Toshio,Hofmann, Alan F.
, p. 18 - 29 (2006)
The chemical synthesis of 3β,7β-dihydroxy-5-cholen-24-oic acid, triply conjugated by sulfuric acid at C-3, by N-acetylglucosamine (GlcNAc) at C-7, and by glycine or taurine at C-24, is described. These are unusual, major metabolites of bile acid found to
A concise synthesis of 25-Hydroxycholesterol from hyodesoxycholic Acid
Jin, Can,Wang, Yulei,Sun, Bin,Su, Weike
, p. 96 - 99 (2018/03/21)
A simple, efficient and economical method has been developed for the synthesis of 25-hydroxycholesterol in seven steps from hyodesoxycholic acid with an overall yield of 39%. The preparation of the 3β-tetrahydropyranyloxychol-5-en-24-al from 3β-tetrahydropyranyloxychol-5-en-24-oic acid methyl ester with di-isobutylaluminium hydride was achieved instead of using the conventional two-step reaction, thus avoiding the use of the toxic oxidant CrO3. The terminal product was obtained by hydroxybromination of desmosterol with N-bromosuccinimide/H2O, followed by reduction and deprotection of the halohydrins with LiAlH4. This simplified route gave an increased overall yield and used economical and environmentally benign reagents.
OXYSTEROLS AND METHODS OF USE THEREOF
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Paragraph 00750, (2018/05/16)
Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.
Investigation on bile acid receptor regulators. Discovery of cholanoic acid derivatives with dual G-protein coupled bile acid receptor 1 (GPBAR1) antagonistic and farnesoid X receptor (FXR) modulatory activity
Sepe, Valentina,Renga, Barbara,Festa, Carmen,Finamore, Claudia,Masullo, Dario,Carino, Adriana,Cipriani, Sabrina,Distrutti, Eleonora,Fiorucci, Stefano,Zampella, Angela
, p. 59 - 67 (2015/12/24)
Bile acids, the end products of cholesterol metabolism, activate multiple mechanisms through the interaction with membrane G-protein coupled receptors including the bile acid receptor GPBAR1 and nuclear receptors such as the bile acid sensor, farnesoid X receptor (FXR). Even if dual FXR/GPBAR1 agonists are largely considered a novel opportunity in the treatment of several liver and metabolic diseases, selective targeting of one of these receptors represents an attractive therapeutic approach for a wide range of disorders in which dual modulation is associated to severe side effects. In the present study we have investigated around the structure of LCA generating a small library of cholane derivatives, endowed with dual FXR agonism/GPBAR1 antagonism. To the best of our knowledge, this is the first report of bile acid derivatives able to antagonize GPBAR1.
Design and synthesis of a crosslinker for studying intracellular steroid trafficking pathways
Byrd, Katherine M.,Arieno, Marcus D.,Kennelly, Megan E.,Estiu, Guillermina,Wiest, Olaf,Helquist, Paul
, p. 3843 - 3851 (2015/07/27)
A crosslinker was designed and synthesized as a molecular tool for potential use in probing the intracellular trafficking pathways of steroids. The design was guided by computational modeling based upon a model for the transfer of cholesterol between two
NEUROACTIVE STEROIDS AND METHODS OF USE THEREOF
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Paragraph 00276, (2014/10/15)
3beta, 17beta disubstituted steroidal compounds, pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof, are provided for the prevention and treatment of a variety of CNS-related conditions.
Total synthesis and pharmacological characterization of solomonsterol A, a potent marine pregnane-X-receptor agonist endowed with anti-inflammatory activity
Sepe, Valentina,Ummarino, Raffaella,D Auria, Maria Valeria,Mencarelli, Andrea,D Amore, Claudio,Renga, Barbara,Zampella, Angela,Fiorucci, Stefano
scheme or table, p. 4590 - 4599 (2011/09/14)
Recently, we reported the identification of a novel class of pregnane-X-receptor (PXR) agonists, solomonsterols A and B, isolated from the marine sponge Theonella swinhoei. Preliminary pharmacological studies demonstrated that these natural compounds are potential leads for the treatment of human disorders characterized by dysregulation of innate immunity. In this article, we describe the first total synthesis of solomonsterol A and its in vivo characterization in animal models of colitis. Using transgenic mice expressing the human PXR, we found that administration of synthetic solomonsterol A effectively protects against development of clinical signs and symptoms of colitis and reduced the generation of TNFα, a signature cytokine for this disorder. In addition, we have provided the first evidence that solomonsterol A might act by triggering the expression of TGFβ and IL-10, potent counter-regulatory cytokines in inflammatory bowel diseases (IBD). Finally, we have shown that solomonsterol A inhibits NF-κB activation by a PXR dependent mechanism. In summary, solomonsterol A is a marine PXR agonist that holds promise in the treatment of inflammation-driven immune dysfunction in clinical settings.
