Aliphatic Substitution of &lt;i&gt;o&lt;/i&gt;-Carboranyl Phenols Enhances Estrogen Receptor Beta Selectivity

Ohta, Kiminori; Ogawa, Tokuo; Kaise, Asako; Oda, Akifumi; Endo, Yasuyuki

doi:10.1248/cpb.c13-00796

Cited by 19 publications

(10 citation statements)

References 34 publications

(46 reference statements)

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“…In particular, n -propyl-substituted o -carborane 42 (Fig. 9) shows an interesting 7.4-fold beta selectivity in ER-binding assays, with RBA values of 11.8% on ERα and of 87% on ERβ [118]. Most importantly, this compound displayed only moderate estrogenic activity in MCF-7 cells and, therefore, may constitute a promising starting point for the development of ERβ-selective carborane-containing ligands.…”

Section: Update On Chemical Classes Comprising Erα and Erβ Modulatorsmentioning

confidence: 99%

Estrogen receptors alpha (ERα) and beta (ERβ): Subtype-selective ligands and clinical potential

et al. 2014

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Estrogen receptors alpha (ERα) and beta (ERβ) are nuclear transcription factors that are involved in the regulation of many complex physiological processes in humans. Modulation of these receptors by prospective therapeutic agents is currently being considered for prevention and treatment of a wide variety of pathological conditions, such as, cancer, metabolic and cardiovascular diseases, neurodegeneration, inflammation, and osteoporosis. This review provides an overview and update of compounds that have been recently reported as modulators of ERs, with a particular focus on their potential clinical applications.

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Section: Update On Chemical Classes Comprising Erα and Erβ Modulatorsmentioning

confidence: 99%

Estrogen receptors alpha (ERα) and beta (ERβ): Subtype-selective ligands and clinical potential

et al. 2014

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“…29 More recently, the same group worked on the synthesis and biological evaluation of carboranyl-based compounds with selective affinity for specific ER subtypes. 30 Nuclear ERs exist in fact as two major subtypes, a and b, which are composed of several domains: DNA binding, hormone binding and activation of transcription domains. A variety of nuclear responses are mediated through the binding of estrogens (17b-estradiol, estrone, estriol, estetrol), or estrogen analogues, to the ligand binding domain (LBD), which transactivates gene expression upon ligand binding.…”

Section: Estrogen Receptor Ligandsmentioning

confidence: 99%

New keys for old locks: carborane-containing drugs as platforms for mechanism-based therapies

et al. 2019

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Icosahedral carboranes in medicine are still an emerging class of compounds with potential beneficial applications in drug design. These highly hydrophobic clusters are potential ''new keys for old locks'' which open up an exciting field of research for well-known, but challenging important therapeutic substrates, as demonstrated by the numerous examples discussed in this review.Key learning points 1. Highlight important receptors (''old locks'') as targets for efficient therapeutic treatments and propose carboranes as new class of drugs (''new keys''). 2. Present the benefits of carboranes as building block in drug design and outline novel carborane-based receptor ligands. 3. Guideline for readers through the versatility of potential medical applications of carborane-containing agents. 4. Current challenges of this novel strategy and the possibilities for structural modifications for enhancing drug properties and effects. 5. Molecular docking strategies available for carborane-based receptor ligands.

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“…Owing to these distinctive properties, carboranes have been regarded as one of the most excellent organic groups to improve performance of organic polymers with remarkable thermal stability . Therefore, carboranes were incorporated into many traditional polymers to improve their thermal stability including epoxy resins, phenolic resins, polyurethanes, organic silicone polymers, benzoxazine resins, polyimides, and so forth.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of carborane‐containing polyester with excellent thermal and ultrahigh char yield

Zeng

et al. 2016

J of Applied Polymer Sci

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A series of wholly carborane‐containing polyesters with high thermostability were successfully synthesized by the catalytic polycondensation of carborane diol monomers with carborane diacid chlorides. They can be used for the preparation of materials of high temperature resistant coatings and adhesive. The influence of solvent, reaction temperature, and reaction time on the molecular weight and yield of the polymers were studied. In comparison with the carborane‐free polyester, the carborane‐containing polyesters showed higher degradation temperature and char yield and lower degradation rate. The thermal gravimetric analyzer (TGA) curves indicate that the carborane group could effectively reduce the degradation rate of carborane‐containing polyesters, which give a char yield of exceeding 64% under air (47% under N2) at 700 °C. Such data are superior to the carborane‐free polyester, which showed a low char yield of around 0.3% under air (5% under N2) at the same condition. Moreover, the thermal transition mechanism of carborane‐containing polyesters was also studied. The FTIR spectra and TG‐FTIR analysis indicate that the carborane cage could react with oxygen to form BOB and BC linkages at elevated temperatures, which postpones the thermal decomposition of polyester and accounts for the high char yield. The newly prepared kind of high temperature polyesters have enormous technical and economic value, especially in the high temperature fields. They can be widely used as raw materials to prepare the high temperature resistant coatings or adhesives for automotive engine, aircraft and other equipments worked in high‐temperature environments. Under high environmental temperature, the good thermal stability is capable of keeping polyesters stable and expanding their service lives. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 44202.

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Aliphatic Substitution of <i>o</i>-Carboranyl Phenols Enhances Estrogen Receptor Beta Selectivity

Cited by 19 publications

References 34 publications

Estrogen receptors alpha (ERα) and beta (ERβ): Subtype-selective ligands and clinical potential

Estrogen receptors alpha (ERα) and beta (ERβ): Subtype-selective ligands and clinical potential

New keys for old locks: carborane-containing drugs as platforms for mechanism-based therapies

Synthesis and characterization of carborane‐containing polyester with excellent thermal and ultrahigh char yield

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