(R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines

Fátima, Ângelo de; Kohn, Luciana Konecny; Antônio, Márcia Aparecida; Carvalho, João Ernesto de; Pilli, Ronaldo A.

doi:10.1016/j.bmc.2005.02.007

Cited by 108 publications

(73 citation statements)

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“…Interestingly, we found that (S)-goniothalamin (IC 50 = 6.4 μM) was 1,600-fold more potent than (R)-goniothalamin (IC 50 = 4.0 nM) in renal 786-0 cancer cells (de Fátima et al, 2006b). As reported for (R)-goniothalamin (Pihie et al, 1998;de Fátima et al, 2005 and cited references), we demonstrated that (S)-goniothalamin exhibited pronounced selectivity for cancer cells, while presenting minor cytotoxicity against non-tumor cells (de Fátima et al, unpublished results). The extremely high antiproliferative activity and selectivity presented by (S)-goniothalamin for 786-0 cell line (IC 50 = 4.0 nM) prompted us to synthesize eigth analogues (compounds 1-8; Fig.…”

Section: Goniothalamin: a Lead Compound For Drug Design?supporting

confidence: 75%

“…2] is the styryl lactone most extensively studied and its promising antiproliferative activity have prompted scientists to investigate with more details its potential as antitumor agent (Zhou et al, 2005;de Fátima et al, 2006a and cited references;Dumitrescu et al, 2010;Wach et al, 2010;Vendramini-Costa et al, 2010;Kasaplar et al, 2010). This natural compound displayed in vitro cytotoxic effect especially by inducing apoptosis in different cancer cell lines (Ali et al, 1997;Pihie et al, 1998;Inayat-Hussain et al, 1999;Inayat-Hussain et al, 2003;Chen et al, 2005;de Fátima et al, 2005;Chan et al, 2006;de Fátima et al, 2008b;Inayat-Hussain et al, 2010). This effect was shown to be selective for cancer cell lines with no significant cytotoxicity toward non-malignant cells (Pihie et al, 1998;de Fátima et al, 2005 and cited references).…”

Section: Goniothalamin: a Lead Compound For Drug Design?mentioning

confidence: 99%

“…This natural compound displayed in vitro cytotoxic effect especially by inducing apoptosis in different cancer cell lines (Ali et al, 1997;Pihie et al, 1998;Inayat-Hussain et al, 1999;Inayat-Hussain et al, 2003;Chen et al, 2005;de Fátima et al, 2005;Chan et al, 2006;de Fátima et al, 2008b;Inayat-Hussain et al, 2010). This effect was shown to be selective for cancer cell lines with no significant cytotoxicity toward non-malignant cells (Pihie et al, 1998;de Fátima et al, 2005 and cited references). In in vivo models, (R)-goniothalamin was reported to have tumoricidal and tumoristatic activities in Sprague-Dawley rats with 7,12-dimethylbenzanthracene (DMBA)-induced mammary tumors and in Ehrlich solid tumor in mice (Meenakshii et al, 2000;Vendramini-Costa et al, 2010).…”

Section: Goniothalamin: a Lead Compound For Drug Design?mentioning

confidence: 99%

See 2 more Smart Citations

The Medicinal Value of Biodiversity: New Hits to Fight Cancer

Justo¹,

Souza²,

Fátima³

et al. 2011

Biological Diversity and Sustainable Resources Use

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Section: Goniothalamin: a Lead Compound For Drug Design?supporting

confidence: 75%

Section: Goniothalamin: a Lead Compound For Drug Design?mentioning

confidence: 99%

Section: Goniothalamin: a Lead Compound For Drug Design?mentioning

confidence: 99%

See 1 more Smart Citation

The Medicinal Value of Biodiversity: New Hits to Fight Cancer

Justo¹,

Souza²,

Fátima³

et al. 2011

Biological Diversity and Sustainable Resources Use

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“…Studies in vitro indicated cytotoxic activity of the GTN natural enantiomer, especially in tumoral cell lineage, such as multiresistant breast cells, and also lung, melanoma, kidney, colon, ovary, and PCas (de Fatima et al 2005). Also, other studies demonstrated pro-apoptotic activity of the R-GTN by means of caspases pathway; increase of BAX pro-apoptotic protein expression; and inhibition of nitric oxide synthase (NOS) (Inayat-Hussain et al 2003, de Fatima et al 2005. Vendramini-Costa et al (2010) verified that racGTN, the same used in the study herein, showed antiedematogenic activity with simultaneous tumoral development inhibition in the solid tumor of Ehrlich.…”

Section: Discussionmentioning

confidence: 99%

“…Goniothalamin was prepared according to a published procedure (de Fatima et al 2005) and it was emulsified with 1% Tween 80 (Synth, Diadema, SP, Brazil) and dissolved in PBS, pH 7.0 (Vendramini-Costa et al 2014). Celecoxib was obtained from CELEBRA (Pfizer Pharmaceuticals LLC, Caguas, Puerto Rico), and diluted in CMC 0.05% (Sozer et al 2011).…”

Section: Drugsmentioning

confidence: 99%

Anti-inflammatory therapies in TRAMP mice: delay in PCa progression

Kido¹,

Montico²,

Sauce³

et al. 2016

Endocrine-Related Cancer

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The aim of this study was to characterize the structural and molecular biology as well as evaluate the immediate and late responses of prostatic cancer in the transgenic adenocarcinoma of the mouse prostate (TRAMP) model after treatment with goniothalamin (GTN) and celecoxib. The treated mice received GTN (150 mg/kg, gavage) or celecoxib (10 mg/kg, gavage) from 8 to 12 weeks of age. They were killed at different ages: the immediate-response groups at 12 weeks and the late-response groups at 22 weeks. The ventral prostate was collected for light microscopy, immunohistochemistry, western blotting, TUNEL, and ELISA. Morphological analyses indicated that GTN treatment delayed the progression of prostatic adenocarcinoma, leading to a significant decrease of prostatic lesion frequency in both experimental period responses to this treatment, mainly high-grade prostatic intraepithelial neoplasia and well-differentiated adenocarcinoma. Also, the celecoxib treatment showed a particular decrease in the proliferative processes (PCNA) in both the experimental periods. Despite celecoxib diminishing the COX2 and IGFR1 levels, GTN presented higher action spectrum considering the decrease of a greater molecular number involved in the proliferative and inflammatory processes in prostatic cancer. Goniothalamin attenuated the pro-inflammatory response in TRAMP prostatic microenvironment, delaying prostate cancer (PCa) progression. Celecoxib treatment was efficient in the regulation of COX2 in the TRAMP mice, mainly in the advanced disease grade. Finally, we concluded that inflammatory process control in early grades of PCa was crucial for the downregulation of the signaling pathways involved in the proliferative processes in advanced cancer grades.

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Olefin Ring‐Closing Metathesis

Yet

2016

Organic Reactions

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The olefin ring‐closing metathesis reaction catalyzed by ruthenium and molybdenum complexes has been employed in the syntheses of carbocycles, heterocycles, supramolecular compounds, and in tandem metathesis reactions. Chiral ruthenium and molybdenum catalysts have provided high enantiomeric and diastereomeric excesses in ring‐closing metathesis reactions. Many of the unsuccessful medium‐ and large‐sized ring formations which were unsuccessful by traditional methods, such as the intramolecular Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski reactions, can now be formed by olefin ring‐closing metathesis reactions. Ring‐closing metathesis has been a key step and sometimes the only successful method for the synthesis of numerous natural products and drug discovery targets. The objective of this chapter is to provide an updated, comprehensive coverage of the literature of the olefin ring‐closing metathesis reaction and related processes. Key mechanistic points are summarized.

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(R)-Goniothalamin: total syntheses and cytotoxic activity against cancer cell lines

Cited by 108 publications

References 50 publications

The Medicinal Value of Biodiversity: New Hits to Fight Cancer

The Medicinal Value of Biodiversity: New Hits to Fight Cancer

Anti-inflammatory therapies in TRAMP mice: delay in PCa progression

Olefin Ring‐Closing Metathesis

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