Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Development of subtype-selective estrogen receptor modulators using the bis(4-hydroxyphenyl)silanol core as a stable isostere of bis(4-hydroxyphenyl)methanol.

ABSTRACT: In this study, we synthesized and evaluated silanol-based bisphenol derivatives as stable isosteres of bis(4-hydroxyphenyl)methanol. The developed silanols exhibited estrogen receptor (ER)-modulating activity. Among them, bis(4-hydroxyphenyl)(methyl)silanol (5a) showed a characteristic ER subtype selectivity, namely, antagonistic activity toward ERα and agonistic activity toward ERβ. Docking simulation indicated that the silanol moiety plays a key role in this selectivity. Our results suggest that silanol-based bisphenols offer a unique scaffold for biologically active compounds.

SUBMITTER: Matsumoto Y

PROVIDER: S-EPMC10496907 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Development of subtype-selective estrogen receptor modulators using the bis(4-hydroxyphenyl)silanol core as a stable isostere of bis(4-hydroxyphenyl)methanol.

Matsumoto Yuichiro Y Hashimoto Yuichi Y Fujii Shinya S

RSC advances 20230912 39

In this study, we synthesized and evaluated silanol-based bisphenol derivatives as stable isosteres of bis(4-hydroxyphenyl)methanol. The developed silanols exhibited estrogen receptor (ER)-modulating activity. Among them, bis(4-hydroxyphenyl)(methyl)silanol (5a) showed a characteristic ER subtype selectivity, namely, antagonistic activity toward ERα and agonistic activity toward ERβ. Docking simulation indicated that the silanol moiety plays a key role in this selectivity. Our results suggest th ...[more]

PMID: 37705989

Similar Datasets

Synthesis and Evaluation of a Stable Isostere of Malonyllysine.

Project description:Lysine malonylation is a recently characterized post-translational modification involved in the regulation of energy metabolism and gene expression. One unique feature of this post-translational modification is its potential susceptibility to decarboxylation, which poses possible challenges to its study. As a step towards addressing these challenges, we report the synthesis and evaluation of a stable isostere of malonyllysine. First, we find that synthetic substitution of the malonyl group with a tetrazole isostere results in amino acid's resistant to thermal decarboxylation. Next, we demonstrate that protected variants of this amino acid are readily incorporated into peptides. Finally, we show that tetrazole isosteres of malonyllysine can be recognized by anti-malonyllysine antibodies and histone deacylases, validating their ability to mimic features of the endogenous lysine modification. Overall, this study establishes a new chemical strategy for stably mimicking a metabolite-derived post-translational modification, providing a foothold for tool development and functional analyses.

| S-EPMC10262540 | biostudies-literature

A Stable Silanol Triad in the Zeolite Catalyst SSZ-70.

Project description:Nests of three silanol groups are located on the internal pore surface of calcined zeolite SSZ-70. 2D 1 H double/triple-quantum single-quantum correlation NMR experiments enable a rigorous identification of these silanol triad nests. They reveal a close proximity to the structure directing agent (SDA), that is, N,N'-diisobutyl imidazolium cations, in the as-synthesized material, in which the defects are negatively charged (silanol dyad plus one charged SiO- siloxy group) for charge balance. It is inferred that ring strain prevents the condensation of silanol groups upon calcination and removal of the SDA to avoid energetically unfavorable three-rings. In contrast, tetrad nests, created by boron extraction from B-SSZ-70 at various other locations, are not stable and silanol condensation occurs. Infrared spectroscopic investigations of adsorbed pyridine indicate an enhanced acidity of the silanol triads, suggesting important implications in catalysis.

| S-EPMC7317713 | biostudies-literature

Synthesis and evaluation of 4-(substituted styryl/alkenyl)-3,5-bis(4-hydroxyphenyl)-isoxazoles as ligands for the estrogen receptor.

Project description:A series of 3,5-bis (4-hydroxyphenyl) isoxazoles bearing a styryl/alkyl vinyl group at the 4-position were prepared and evaluated as ligands for the estrogen receptor-alpha (ERα). The target compounds were prepared using the Suzuki reaction to couple an iodo-isoxazole intermediate with a series of styryl/alkenyl boronic acids, followed by O-demethylation. The products were evaluated for their estrogen receptor-α ligand binding domain (ERα-LBD) binding affinity using a competitive binding assay. The 4-(4-hydroxystyryl) derivative 4h displays binding properties similar to those of the previously described pyrazole class of ER ligands, indicating that the ERα-LBD tolerates the presence of the added vinyl group at the 4-position of the isoxazole ring.

| S-EPMC3444814 | biostudies-literature

Bis[μ-2-(4-hydroxyphenyl)acetato]-κO,O':O;κO:O,O'-bis{aqua(4,4'-bi-pyri-dine-κN)bis[2-(4-hydroxyphenyl)acetato-κO,O']gadolinium(III)} monohydrate.

Project description:In the dinuclear title complex, [Gd(2)(C(8)H(7)O(3))(6)(C(10)H(8)N(2))(2)(H(2)O)(2)]·H(2)O, the two Gd(III) ions are nine-coordinated by seven O atoms from four deprotonated p-hy-droxy-phenyl-acetic acid (PAA) ligands, one water O atom and an N atom from a 4,4'-bypyridine (bipy) ligand in a distorted tricapped trigonal-prismatic geometry. The deprotonated PAA ligands are coordinated to the Gd(III) atom either as chelating on the same metal or in a tridentate bridging mode. Numerous O-H⋯O and O-H⋯N hydrogen bonds involving hydroxyl, coordinated and uncoordinated water mol-ecules build up an intricate three-dimensional network.

| S-EPMC3009044 | biostudies-literature

1,5-Bis[(E)-1-(2-hydroxyphenyl)ethyl-idene]thiocarbonohydrazide mono-hydrate.

Project description:In the title compound, C(17)H(18)N(4)O(2)S·H(2)O, the thio-urea derivative is almost planar, with an r.m.s. deviation for the non-H atoms of 0.057?Å. The hydroxyl groups lie to the same side of the mol-ecule as the thione S atom, a conformation that allows the formation of intra-molecular O-H?S and O-H?N hydrogen bonds. In the crystal structure, the thio-urea and water mol-ecules self-assemble into a two-dimensional array by a combination of O(water)-H?O(hydrox-yl), N-H?O(water) and O(water)-H?S hydrogen bonds and C-H?? inter-actions.

| S-EPMC2983601 | biostudies-literature

Bis[(1-methyl-1H-benzimidazol-2-yl)methanol-κN,O]bis-(thio-cyanato-κN)cobalt(II) methanol solvate.

Project description:In the mononuclear title complex, [Co(NCS)(2)(C(9)H(10)N(2)O)(2)]·CH(3)OH, the cobalt(II) ion is surrounded by two (1-methyl-1H-benzimidazol-2-yl)methanol bidentate ligands and two thio-cyanate ligands, and exhibits a distorted octa-hedral coordination by four N atoms and two O atoms. The structure is consolidated by hydrogen bonds between the organic ligand, thio-cyanate anion and the uncoordinated methanol mol-ecule, leading to a chain along [100].

| S-EPMC2979919 | biostudies-literature

Bis(ethyl-enediamine-κ(2)N,N')bis-(methanol-κO)copper(II) benzene-1,4-dicarboxyl-ate methanol disolvate.

Project description:In the cation of the title compound, [Cu(C(2)H(8)N(2))(2)(CH(3)OH)(2)](C(8)H(4)O(4))·2CH(3)OH, the Cu(II) atom lies on an inversion centre. The four N atoms of two ethyl-enediamine ligands around the Cu(II) atom form the equatorial plane, while two methanol O atoms in the axial positions complete a Jahn-Teller distorted octa-hedral coordination. The benzene-1,4-dicarboxyl-ate anion is centrosymmetric. In the crystal, C-H⋯O, N-H⋯O and O-H⋯O hydrogen bonds link the cations, the anions and the methanol solvent mol-ecules.

| S-EPMC3393248 | biostudies-literature

Synthesis of 9,9-bis(4-hydroxyphenyl) fluorene catalyzed by bifunctional ionic liquids.

Project description:Through structural design, a series of bifunctional ionic liquids (BFILs) containing sulfonic acid (-SO3H) and sulfhydryl groups (-SH) were synthesized and characterized by NMR and MS. The acidity of these BFILs was measured by the Hammett acidity (H 0) and the effective sulfhydryl molar content of BFILs was determined by Ellman's method. Moreover, BFIL's catalytic properties in the condensation reaction of 9-fluorenone and phenol were studied. BFIL catalyst 6c can achieve nearly 100% conversion of 9-fluorenone with a high selectivity of 9,9-bis(4-hydroxyphenyl) fluorene (95.2%).

| S-EPMC9041788 | biostudies-literature

trans-Bis(1,3-diphenyl-propane-1,3-dionato)(methanol)oxidovanadium(IV) methanol disolvate.

Project description:In the title compound, [V(C15H11O2)2O(CH3OH)]·2CH3OH, the V(IV) atom is coordinated by two 1,3-diphenyl-propane-1,3-dionate ligands and an oxide ligand in an axial position. The sixth position is occupied by the O atom of a methanol group bonded trans to the oxide atom. The octa-hedral geometry is significantly distorted, with the V(IV) atom lying 0.330 (3) Å above the equatorial plane formed by the O atoms of the two β-diketonate ligands. In the crystal, O-H⋯O hydrogen bonds between the coordinating methanol group in the complex and the two methanol solvent mol-ecules lead to the formation of polymeric chains along the c-axis direction. Weak C-H⋯O contacts are also observed.

| S-EPMC3588710 | biostudies-literature

Bis(methanol-κO)bis-(1,2-diamino-2-hy-droxy-imino-ethanone oximato-κ(2)N,N')copper(II) bis-(oxamide dioxime) methanol disolvate.

Project description:In the title compound, [Cu(C(2)H(5)N(4)O(2))(2)(CH(3)OH)(2)]·2C(2)H(6)N(4)O(2)·2CH(3)OH, the Cu(II) atom, lying on an inversion center, is coordinated by four N atoms from two 1,2-diamino-2-hy-droxy-imino-ethanone oximate anion and two O atoms from two methanol mol-ecules in a distorted octa-hedral geometry. The two uncoordinating oxamide dioxime mol-ecules, each lying on an inversion center, adopt a trans conformation. In the crystal, O-H⋯O, N-H⋯O and N-H⋯N hydrogen bonds link the complex mol-ecules and the oxamide dioxime and methanol mol-ecules.

| S-EPMC3470128 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data