6967-44-8Relevant academic research and scientific papers
Optical control of protein activity and gene expression by photoactivation of caged cyclofen
Hamouri, Fatima,Zhang, Weiting,Aujard, Isabelle,Le Saux, Thomas,Ducos, Bertrand,Vriz, Sophie,Jullien, Ludovic,Bensimon
, p. 1 - 23 (2019/05/07)
The use of light to control the expression of genes and the activity of proteins is a rapidly expanding field. While many of these approaches use a fusion between a light activatable protein and the protein of interest to control the activity of the latter, it is also possible to control the activity of a protein by uncaging a specific ligand. In that context, controlling the activation of a protein fused to the modified estrogen receptor (ERT) by uncaging its ligand cyclofen-OH has emerged as a generic and versatile method to control the activation of proteins quantitatively, quickly and locally in a live organism. Here, we present the experimental details behind this approach.
POLYMER AND METHOD FOR USING THE SAME
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Page/Page column 12-13, (2018/05/03)
The invention relates to a polymer derived from: reaction of glycidyl (meth)acrylate, allyl glycidyl ether or [(vinyloxy)methyl]oxirane with ammonia or primary amine to obtain a mixture of monomer compounds; reaction of the mixture of monomer compounds with at least one of acrylic acid, vinyl alcohol, vinyl acetate, acrylamide, methylacrylic acid, and methylacrylamide to obtain an intermediate polymer; and reaction of the intermediate polymer with a dithiocarbamic acid salt. Methods for using the polymer are also described herein.
SYNTHESIS OF PHOTOACTIVABLE CAGED CYCLOFEN-OH AND DERIVATIVES THEREOF
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Page/Page column 18, (2018/01/15)
The present invention relates to a new process of manufacturing of caged cyclofen-OH and derivatives thereof, of formula (I) or salts thereof, wherein n, R1, R1 ', R2, and R3 are as defined in the claims.
Synthesis and evaluation of fluoroethyl cyclofenil analogs: Models for potential estrogen receptor imaging agent
Zhu, Hua,Yang, Zhi,Lin, Jian-Guo,Luo, Shi-Neng,Shen, Yu-Mei
scheme or table, p. 46 - 52 (2012/07/28)
Cyclofenil analogs (2a-2f) and their fluorine-containing derivatives (3a-3f) were synthesized and evaluated as candidate ligands for positron emission tomography (PET) imaging of estrogen receptors. Most of them show relatively high binding affinities comparable with estradiol (E2). (4-Fluoroethoxyphenyl)-(4-hydroxyphenyl) methylenecyclopentane (3a) showed both the highest binding affinity for ERs (88.6 for ERβ, 13.8 for ERα) and highest β/α ratio (β/α for 6.4-fold). The radioactive compound [18F]3a was prepared via displacement of the corresponding mesylate precursor 4 with [18F]fluoride (18F: β+; 96.7%, T1/2 = 109.8 min). The biodistribution studies in immature female SD rats demonstrated that the uptake in the uterus and ovaries were 1.358 ± 0.089% ID/g, 1.439 ± 0.214% ID/g, respectively, both of the ratios of uterus/blood and ovaries/blood was less than 2:1. Micro-PET imaging of immature female SD rats has also been reported.
SILICONE (METH)ACRYLAMIDE MONOMER, POLYMER, OPHTHALMIC LENS, AND CONTACT LENS
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Page/Page column 37, (2011/10/10)
The present invention relates to a silicone (meth)acrylamide monomer, and this silicone (meth)acrylamide monomer is particularly suitable for use in contact lenses, intraocular lenses, artificial cornea, and the like.
Photocontrol of protein activity in cultured cells and zebrafish with one- and two-photon illumination
Sinha, Deepak Kumar,Neveu, Pierre,Gagey, Nathalie,Aujard, Isabelle,Benbrahim-Bouzidi, Chouaha,Le Saux, Thomas,Rampon, Christine,Gauron, Carole,Goetz, Bernard,Dubruille, Sylvie,Baaden, Marc,Volovitch, Michel,Bensimon, David,Vriz, Sophie,Jullien, Ludovic
experimental part, p. 653 - 663 (2011/03/17)
We have implemented a noninvasive optical method for the fast control of protein activity in a live zebrafish embryo. It relies on releasing a protein fused to a modified estrogen receptor ligand binding domain from its complex with cytoplasmic chaperones, upon the local photoactivation of a nonendogenous caged inducer. Molecular dynamics simulations were used to design cyclofen-OH, a photochemically stable inducer of the receptor specific for 4-hydroxy-tamoxifen (ERT2). Cyclofen-OH was easily synthesized in two steps with good yields. At submicromolar concentrations, it activates proteins fused to the ERT2 receptor. This was shown in cultured cells and in zebrafish embryos through emission properties and subcellular localization of properly engineered fluorescent proteins. Cyclofen-OH was successfully caged with various photolabile protecting groups. One particular caged compound was efficient in photoinducing the nuclear translocation of fluorescent proteins either globally (with 365 nm UV illumination) or locally (with a focused UV laser or with two-photon illumination at 750 nm). The present method for photocontrol of protein activity could be used more generally to investigate important physiological processes (e.g., in embryogenesis, organ regeneration and carcinogenesis) with high spatiotemporal resolution.
Practical synthesis of FEt-penta-cyclofenil and its derivatives for potential PET imaging
Zhu, Hua,Huang, Liliang,Xu, Xiaoping,Shen, Yu-Mei
experimental part, p. 3322 - 3331 (2011/01/04)
Generally, FEt-penta-cyclofenil and its derivatives have greater relative binding affinity to estradiol receptors than estradiol. (4-Fluoroethoxyphenyl)- (4'-hydroxyphenyl) methylenecyclopentane and its derivatives were synthesized for potential radioactive image agents, and their structures were characterized by ultraviolet, infrared, 1H NMR, 19F NMR, and high-resolution mass spectrometry. Copyright
Characterization of the pharmacophore properties of novel selective estrogen receptor downregulators (SERDs)
Kieser, Karen J.,Kim, Dong Wook,Carlson, Kathryn E.,Katzenellenbogen, Benita S.,Katzenellenbogen, John A.
scheme or table, p. 3320 - 3329 (2010/09/11)
Selective estrogen receptor (ER) down-regulators (SERDs) reduce ERα protein levels as well as block ER activity and therefore are promising therapeutic agents for the treatment of hormone refractory breast cancer. Starting with the triarylethylene acrylic acid SERD 4, we have investigated how alterations in both the ligand core structure and the appended acrylic acid substituent affect SERD activity. The new ligands were based on high affinity, symmetrical cyclofenil or bicyclo[3.3.1]nonane core systems, and in these, the position of the carboxyl group was extended from the ligand core, either retaining the vinylic linkage of the substituent or replacing it with an ether linkage. Although most structural variants showed binding affinities for ERα and ERβ higher than that of 4, only the compounds preserving the acrylic acid side chain retained SERD activity, although they could possess varying core structures. Hence, the acrylic acid moiety of the ligand is crucial for SERD-like blockade of ER activities.
Design, synthesis, and evaluation of cyclofenil derivatives for potential SPECT imaging agents
Zhu, Hua,Huang, Liliang,Zhang, Yuanqing,Xu, Xiaoping,Sun, Yanhong,Shen, Yu-Mei
experimental part, p. 591 - 599 (2011/10/18)
To develop technetium- and rhenium-labeled nonsteroidal estrogen imaging agents for estrogen receptor (ER) positive breast tumors, two groups of rhenium and technetium cyclofenil derivatives were synthesized and characterized. The binding affinities of the rhenium complexes for ERs were determined. The tricarbonyl rhenium complex showed the highest binding affinity for ERs (81.2 for ERβ, 16.5 for ERα). Tricarbonyl technetium cyclofenil complexes were obtained in high radiochemical purity and radiochemical yields. The results of studies of their octanol/water partition and in vitro stability are presented. These results demonstrate that these radiolabeled cyclofenil derivatives may be considered as potential breast cancer imaging agents. SBIC 2010.
Olefinically unsaturated phosphonate compounds, polymers made therefrom and their use
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Page/Page column 16, (2010/05/13)
This invention relates to compounds of formulae (1 a) and (1 b) wherein R means H or C1- to C6-alkyl, X means a bivalent linking group comprising from one to 12 carbon atoms, Y means a linking group comprising at least one carbon atom, and at least one oxygen atom, or at least one nitrogen atom or both and being at least trivalent, Z means a cation, and n means an integer being two or higher.
