1-Benzyl-2-phenylindole- and 1,2-diphenylindole-based antiestrogens. Estimation of agonist and antagonist activities in transfection assays

Biberger, Christian; Angerer, E. von

doi:10.1016/s0960-0760(97)00197-0

Cited by 33 publications

(25 citation statements)

References 15 publications

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“…After binding of hormonally active compounds to the ER, the resulting ER/drug conjugates interact after dimerization with the ERE at the plasmid and activate the reporter sequence which codes for luciferase. The expression of luciferase correlates very well with the estrogenic potency of the drug [19].…”

Section: Biological Activitymentioning

confidence: 91%

Synthesis, Structural Evaluation, and Estrogen Receptor Interaction of 4, 5‐Bis(4‐hydroxyphenyl)imidazoles

Gust

Keilitz

Schmidt

et al. 2002

Archiv der Pharmazie

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4,5-Bis(4-hydroxyphenyl)imidazoles with 2,2'-H (1),2,2'-F (2),2,2'-Cl (3), and 2,2'6-Cl (4) substituents in the aromatic rings were synthesized by oxidation of the respective methoxy-substituted (R,S)/(S,R)-4,5-diaryl-2-imidazolines with MnO2 and subsequent ether cleavage with BBr3. N-alkylation of 1 and 3 with ethyl iodide yielded the compounds 5 and 6. The imidazoles were characterized by NMR spectroscopy and tested for estrogen receptor binding in a competition experiment with [3H]estradiol using calf uterine cytosol. Gene activation was verified in a luciferase assay using estrogen receptor positive MCF-7-2a cells stably transfected with the plasmid ERE(wtc)luc. All halide substituted imidazoles competed with estradiol for the binding site at the estrogen receptor. The N-ethyl derivative 6 showed the highest relative binding affinity of 1.26 %. Treatment of MCF-7-2a cells, however, did not lead to gene activation. The relative activation of 6 amounted only to 10% at 1 microM compared to E2 (100%).

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Section: Biological Activitymentioning

confidence: 91%

Synthesis, Structural Evaluation, and Estrogen Receptor Interaction of 4, 5‐Bis(4‐hydroxyphenyl)imidazoles

Gust

Keilitz

Schmidt

et al. 2002

Archiv der Pharmazie

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“…In 2009, a second class of phenylindole dendrimer conjugates have been developed [162]. These class of ER ligands (2-phenylindoles) have been previously shown to inhibit mammary tumor growth [163] and, as for EDC, the polyamine conjugation process allowed indoles to retain an high binding affinity for ER [162].…”

Section: The Extranuclear Er Mechanisms As Targets For Anticancer Drugsmentioning

confidence: 99%

Current and Future Development of Estrogen Receptor Ligands: Applications in Estrogen-Related Cancers

Bolli

Marino²

2011

EMI

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17β;-Estradiol (E2), via its cognate receptors (ERs), regulates several aspects of human physiology including development, reproduction and tissue homeostasis. Consequently, E2 could also be implicated in the development or progression of several pathologies, including cancer. Two different ER subtypes are present in mammals (ERβ and ERβ), which display specific roles in E2-related cancers, different tissue distribution, and multiple action mechanisms (i.e., genomic and extranuclear mechanisms). Here, the complex pattern of the relative contribution of each ER subtype in the E2- dependent cancers has been summarized by taking into consideration the molecular events which occur both in the nucleus and in extranuclear compartments. In the second part of this paper, we reviewed the current literature available on the drug-targeting of the ERs, as well as the recent literature and patents describing new and upcoming molecules. These new molecules will probably greatly improve the repertoire of anti-hormonal therapeutic strategies. However, further new drug design programs, which should include all molecular mechanisms at the basis of ER biology, are needed to expand the anti-ER treatments in new and more efficient therapeutic directions. This review also outlines relevant patents.

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“…Several groups including our own have shown that the structure of the side chain in steroidal and non-steroidal antiestrogens is crucial for the degree of antagonism that can be reached [4,8,9] . The main role of the carrier molecule is to guarantee both receptor binding and the correct orientation of the side chain inside the binding pocket.…”

Section: Introductionmentioning

confidence: 99%

Antiestrogenic Activities of 3,8-Dihydroxy-6,11-dihydrobenzo[a]carbazoles with Sulfur-Containing Side Chains

Golob

Biberger

Walter

et al. 2000

Arch. Pharm. Pharm. Med. Chem.

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1-Benzyl-2-phenylindole- and 1,2-diphenylindole-based antiestrogens. Estimation of agonist and antagonist activities in transfection assays

Cited by 33 publications

References 15 publications

Synthesis, Structural Evaluation, and Estrogen Receptor Interaction of 4, 5‐Bis(4‐hydroxyphenyl)imidazoles

Synthesis, Structural Evaluation, and Estrogen Receptor Interaction of 4, 5‐Bis(4‐hydroxyphenyl)imidazoles

Current and Future Development of Estrogen Receptor Ligands: Applications in Estrogen-Related Cancers

Antiestrogenic Activities of 3,8-Dihydroxy-6,11-dihydrobenzo[a]carbazoles with Sulfur-Containing Side Chains

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