Design and synthesis of novel 3-hydroxy-cyclobut-3-ene-1,2-dione derivatives as thyroid hormone receptor β (TR-β) selective ligands

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 14, 2008, Pages 3919-3924

  Raval, Saurin ^a   Raval, Preeti ^a   Bandyopadhyay, Debdutta ^a   Soni, Krunal ^a   Yevale, Digambar ^a   Jogiya, Digvijay ^a   Modi, Honey ^a   Joharapurkar, Amit ^a   Gandhi, Neha ^a   Jain, Mukul R ^a   Patel, Pankaj R ^a  

^a ZYDUS RESEARCH CENTRE   (India)

Author keywords

3 Hydroxy cyclobut 3 ene 1,2 dione; Squaric acid; Thyroid hormone receptor; Thyroid receptor assay; TR Selective

Indexed keywords

3 [3,5 DICHLORO 4 (4 HYDROXY 3 ISOPROPYLPHENOXY)PHENYLAMINO] 4 HYDROXYCYCLOBUT 3 ENE 1,2 DIONE; 3 HYDROXYCYCLOBUT 3 ENE 1,2 DIONE DERIVATIVE; THYROID HORMONE RECEPTOR BETA; THYROMIMETIC AGENT;

ARTICLE; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLOGRAPHY, X-RAY; CYCLOBUTANES; DRUG DESIGN; HUMANS; LIGANDS; LUCIFERASES; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PHENYL ETHERS; PHENYLACETATES; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; THYROID GLAND; THYROID HORMONE RECEPTORS ALPHA; THYROID HORMONE RECEPTORS BETA;

EID: 47349124043     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.038     Document Type: Article

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36. +.
37. 4 CV-1 cells were plated in each well of a 24-well cell culture plate. The cells were transfected 16 h after seeding with a plasmid bearing three copies of TRE cloned upstream of luciferase gene along with a plasmid expressing either the full length human thyroid receptor-α or -β isoform and a third plasmid expressing β-galactosidase. The transfection is carried out using polyfect reagent from Invitrogen, Inc. (Carlsbad, CA). The medium is replaced 6 h post transfection with fresh media having different concentrations of the agonist. The concentration of agonist is adjusted in such a way that the concentration of the solvent (DMSO) in each well is maintained at 1%. The plates are incubated at 37 °C for 16 h before lysing and assaying the luciferase activity using commercially available Glo-lysis kit from Promega and a standard luminometer. The β-galactosidase activity was measured by using the β-galactosidase assay kit from Promega and the absorbance was read at 415 nM.