ArticleJournal of medicinal chemistry2008
Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of SRC homology 2 domain-containing protein tyrosine phosphatase-2 activity.
Article in Journal of medicinal chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 37 citations in OpenAlex.
- Recent advances in adamantane-linked heterocycles: synthesis and biological activity.Molecular diversity · 2026Review
- Synthesis and evaluation of nitroheterocyclic aromatic adamantane amides with trypanocidal activity. Part II.RSC medicinal chemistry · 2026Article
- Grb2 binding induces phosphorylation-independent activation of Shp2.Communications biology · 2021Article
- Synthesis and evaluation of novel 2,4-disubstituted arylthiazoles againstRSC medicinal chemistry · 2020Article
- 3-Cl-AHPC inhibits pro-HGF maturation by inducing matriptase/HAI-1 complex formation.Journal of cellular and molecular medicine · 2019Article
- Nuclear receptor 4A (NR4A) family - orphans no more.The Journal of steroid biochemistry and molecular biology · 2016Article
- Insights into Orphan Nuclear Receptors as Prognostic Markers and Novel Therapeutic Targets for Breast Cancer.Frontiers in endocrinology · 2015Review
- Therapeutic potential of targeting the oncogenic SHP2 phosphatase.Journal of medicinal chemistry · 2014Article
- Minireview: role of orphan nuclear receptors in cancer and potential as drug targets.Molecular endocrinology (Baltimore, Md.) · 2014Review
- Loss of SHP-2 activity in CD4+ T cells promotes melanoma progression and metastasis.Scientific reports · 2013Article
- Targeting protein tyrosine phosphatase SHP2 for the treatment of PTPN11-associated malignancies.Molecular cancer therapeutics · 2013Article
- The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.Chemical reviews · 2013Review
- Ion-exchange-resin-catalyzed adamantylation of phenol derivatives with adamantanols: Developing a clean process for synthesis of 2-(1-adamantyl)-4-bromophenol, a key intermediate of adapalene.Beilstein journal of organic chemistry · 2012Article
- Anti-tumor activity of a novel HS-mimetic-vascular endothelial growth factor binding small molecule.PloS one · 2012Article
- Role of nuclear receptor SHP in metabolism and cancer.Biochimica et biophysica acta · 2011Review
- Ligand-dependent regulation of the activity of the orphan nuclear receptor, small heterodimer partner (SHP), in the repression of bile acid biosynthetic CYP7A1 and CYP8B1 genes.Molecular endocrinology (Baltimore, Md.) · 2011Article
- Article
- Insights into the binding mode and mechanism of action of some atypical retinoids as ligands of the small heterodimer partner (SHP).Journal of computer-aided molecular design · 2010Article
- Novel polymorphisms of nuclear receptor SHP associated with functional and structural changes.The Journal of biological chemistry · 2010Article
- Targeting protein tyrosine phosphatases for anticancer drug discovery.Current pharmaceutical design · 2010Review
Corrections and comments
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Authors and funding
22 authors at 1 institution in 2 countries.
Funding
Abstract
(E)-4-[3-(1-Adamantyl)-4'-hydroxyphenyl]-3-chlorocinnamic acid (3-Cl-AHPC) induces the cell-cycle arrest and apoptosis of leukemia and cancer cells. Studies demonstrated that 3-Cl-AHPC bound to the atypical orphan nuclear receptor small heterodimer partner (SHP). Although missing a DNA-binding domain, SHP heterodimerizes with the ligand-binding domains of other nuclear receptors to repress their abilities to induce or inhibit gene expression. 3-Cl-AHPC analogues having the 1-adamantyl and phenolic hydroxyl pharmacophoric elements replaced with isosteric groups were designed, synthesized, and evaluated for their inhibition of proliferation and induction of human cancer cell apoptosis. Structure-anticancer activity relationship studies indicated the importance of both groups to apoptotic activity. Docking of 3-Cl-AHPC and its analogues to an SHP computational model that was based on the crystal structure of ultraspiracle complexed with 1-stearoyl-2-palmitoylglycero-3-phosphoethanolamine suggested why these 3-Cl-AHPC groups could influence SHP activity. Inhibitory activity against Src homology 2 domain-containing protein tyrosine phosphatase 2 (Shp-2) was also assessed. The most active Shp-2 inhibitor was found to be the 3'-(3,3-dimethylbutynyl) analogue of 3-Cl-AHPC.
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Registered trials
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.