6′-Substituted naphthalene-2-car☐ylic acid analogs, a new class of retinoic acid receptor subtype-specific ligands

Graupner, Gerhart; Malle, Ge ́rard; Maignan, Jean; Lang, Gérard; ́ras, Michel Prunie; Pfahl, Magnus

doi:10.1016/0006-291x(91)91750-7

Cited by 67 publications

(44 citation statements)

References 23 publications

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“…Recently, the affinities of Ro13-7410, TTAB, TTNN and Am580 to the recombinant ligandbinding domains of nuclear RAR were determined (Crettaz et al, 1990). Nevertheless, the relative binding affinities of these compounds, determined by Crettaz et al are , TTAB, TTNN, Am80 and Am580 in a chloramphenicol-acetyltransferase-receptor-activation assay (Lehmann et al, 1991 ;Graupner et al, 1991) are in agreement with those determined by the absorption assay in the present study. Binding experiments carried out with nuclear extracts from COS-7 cells transfected with vectors expressing RARa (Cavey et al, 1990;Delescluse et al, 1991 ;Martin et al, 1992) show for TTAB as well higher as lower affinities for RARa compared to the data presented in this work.…”

Section: Retinoidsupporting

confidence: 89%

In vivo biological activity of retinoids partially correlates to their affinity to recombinant retinoic‐acid receptor α and recombinant‐cellular retinoic‐acid‐binding protein I

Keidel

Szardenings

Mueller

1993

European Journal of Biochemistry

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Several known and some new retinoids were synthesized and their in vivo activity was investigated by an assay, based on induction of alkaline phosphatase in P19 teratocarcinoma cells, human prostate carcinoma cells and primary cultures of neonatal rat heart cells. The assay used in this study was found to be reproducible and useful for rapid screening of retinoids for biological activity. Two newly synthesized compounds exhibit high biological activity. The biological potency of the compounds was compared to their ability to bind to recombinant retinoic-acid receptor a and to cellular retinoic-acid-binding protein I determined by Charsorb-binding assay. mRNA of both retinoic-acid-binding proteins could be detected in the three cell lines investigated. As expected from the number of different retinoic-acid receptors, the results suggest that retinoids do not need to bind retinoic-acid receptor a nor cellular retinoic-acid-binding protein I in order to exhibit biological activity, but most retinoids investigated show a clear correlation between binding to these proteins and their biological activity.

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Section: Retinoidsupporting

confidence: 89%

In vivo biological activity of retinoids partially correlates to their affinity to recombinant retinoic‐acid receptor α and recombinant‐cellular retinoic‐acid‐binding protein I

Keidel

Szardenings

Mueller

1993

European Journal of Biochemistry

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“…Abnormal expression of RAR-P mRNA has been reported for some hepatoma cells and in human oral and epidermal squamous cell carcinoma cell lines (Hu et al, 1991). RAR--mRNA has been shown to be abundantly expressed in the skin (Krust et al, 1989 Graupner et al, 1991).…”

Section: Retinoidsmentioning

confidence: 99%

“…In addition, another subfamily of nuclear receptors (termed RXRs) which might mediate some of the effects of RA or its different metabolites, has been described (Mangelsdorf et al, 1990;Yu et al, 1991;Heyman et al, 1992). It has also been shown that RA and synthetic retinoids have different receptor affinities and each receptor has a different potency in stimulating transcription of target genes (Astrom et al, 1990;Graupner et al, 1991;Delelcuse et al, 1991). Nevertheless, the exact mechanism of action by which RA and retinoids work is still to be elucidated.…”

mentioning

confidence: 99%

Retinoic acid receptors in retinoid responsive ovarian cancer cell lines detected by polymerase chain reaction following reverse transcription

Harant¹,

Korschineck²,

Krupitza³

et al. 1993

Br J Cancer

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Summary The growth inhibitory effects of all-trans and 13-cis retinoic acid (RA) and of the synthetic retinoids TTNPB, TTNPB-ethylester and TTNN were studied on seven human epithelial ovarian cancer cell lines and one ovarian teratocarcinoma cell line. Six of seven ovarian adenocarcinoma cell lines were inhibited in their growth by RA and by synthetic retinoids in a dose dependent manner. No response to these substances was observed for the ovarian teratocarcinoma cell line. The knowledge that RA and retinoids exert their action on the cells via nuclear receptors led us to examine the expression of RAR-a, -,B and -mRNA by these cell lines by polymerase chain reaction following reverse transcription. All cell lines expressed RAR-x and -mRNA and six of the eight cell lines were found to express additionally RAR-P mRNA, among them the ovarian teratocarcinoma cell line. Our data indicate that there was no direct association between the presence of RAR subtype transcripts and the response to retinoids in ovarian cancer cell lines.Retinoic acid (RA) is a morphogenic compound involved in vertebrate development (Eichele, 1989) and it plays a major role in epithelial cell growth and cellular differentiation (Sporn et al., 1984). RA induces differentiation of mouse embryonal carcinoma cells in vitro and influences the development of the regenerating amphibian limb (for review see de Luca, 1991).It has also been shown that retinoids cause growth inhibition in many hyperproliferating cell lines, a feature that makes the compounds of fundamental interest as antitumour agents. Retinoids prevent the development of cancer of the skin and are effective as agents in the treatment of human premalignant and malignant cutaneous disorders (Lippman & Meyskens, 1989). In addition, retinoids are successfully used in the therapy of the acute promyelocytic leukaemia (Meng-er et al., 1988).Several intracellular proteins interacting with RA have been identified, such as the cellular retinoic acid binding protein (CRABP) and the nuclear retinoic acid receptors (RARs). Three RAR subtypes RAR-a, -P and -y have been identified so far (Petkovich et al., 1987;Giguere et al., 1987;Benbrook et al., 1988;Brand et al., 1988;Krust et al., 1989 NIH:OVCAR-3 and the ovarian teratocarcinoma cell line CRL 1572 (PA-1) were received from the American Tissue Type Culture Collection (ATCC, Rockville, MD, USA). All cell lines were cultivated in a-MEM (Gibco, Scotland) supplemented with 10% heat-inactivated foetal calf serum (Gibco, Scotland) and were maintained in an humidified 5% CO2 atmosphere at 37°C. Cultures were refed after 4 days and passaged weekly 1:5 -1:10.All cells were used within 30 passages from the original stock.Tests for mycoplasma contamination were negative (DAPI, Boehringer Mannheim, Germany). RetinoidsAll-trans RA, 1 3-cis RA, (E)-4- [2-(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-2-naphthalenyl)-1-propenyl] benzoic acid -(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-2-

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“…To support this, RARy transcriptionally active AHPN derivatives and analogues were also reported to inhibit growth and induce apoptosis (28,48,49). Other reports present data strongly suggesting an RAR-independent pathway, such as growth inhibition and apoptosis of retinoid-resistant cancer cells (13,14,21,27,42,44,50). 3 Our results support the latter by showing that MM 11453, although unable to activate retinoid receptors on a reporter with the efficacy of standard retinoids or AHPN, strongly inhibited growth and induced apoptosis in retinoid-resistant cancer cell lines.…”

Section: Resultsmentioning

confidence: 86%

A Novel Molecular Target for Breast Cancer Prevention and Treatment

Zhang¹

2003

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6′-Substituted naphthalene-2-car☐ylic acid analogs, a new class of retinoic acid receptor subtype-specific ligands

Cited by 67 publications

References 23 publications

In vivo biological activity of retinoids partially correlates to their affinity to recombinant retinoic‐acid receptor α and recombinant‐cellular retinoic‐acid‐binding protein I

In vivo biological activity of retinoids partially correlates to their affinity to recombinant retinoic‐acid receptor α and recombinant‐cellular retinoic‐acid‐binding protein I

Retinoic acid receptors in retinoid responsive ovarian cancer cell lines detected by polymerase chain reaction following reverse transcription

A Novel Molecular Target for Breast Cancer Prevention and Treatment

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