Cytotoxic Effect (on Tumor Cells) and in Vitro Antiviral Activity against Herpes Simplex Virus of Synthetic Spongiane Diterpenes

Betancur‐Galvis, Liliana; Zuluaga, Carmen; Arnó, Manuel; González, Miguel A.; Zaragozá, Ramón J.

doi:10.1021/np010206t

Cited by 41 publications

(38 citation statements)

References 16 publications

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“…T2 and T3 are semisynthetic compounds produced by reducing either the furan or 17β carboxylic acid functionalities in T1 , respectively. Spongian diterpenoids have been previously investigated for in vitro antiviral and antitumor activities (46). This is the first report that diterpenoids have antiandrogen activity as shown by: 1) inhibition of androgen-dependent proliferation while having no effect on cells that do not depend on AR for growth and survival; 2) blocking AR transcriptional activity measured by reporter gene constructs and endogenous gene expression; 3) specificity for AR with no effect on GR transcriptional activity and no effect on the proliferation of cells that do not express functional AR; 4) competing with androgen for the LBD; 5) blocking androgen-induced N/C interaction; and 6) reducing the weight of androgen-dependent tissue in vivo while having no effect on body weight.…”

Section: Discussionmentioning

confidence: 99%

Spongian Diterpenoids Inhibit Androgen Receptor Activity

Yang

Meimetis

Tien

et al. 2013

Molecular Cancer Therapeutics

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Androgen receptor (AR) is a ligand-activated transcription factor and a validated drug target for all stages of prostate cancer. Antiandrogens compete with physiological ligands for AR ligand-binding domain (LBD). High-throughput screening of a marine natural product library for small molecules that inhibit AR transcriptional activity yielded the furanoditerpenoid spongia-13(16),-14-dien-19-oic acid, designated terpene 1 (T1). Characterization of T1 and the structurally related semi-synthetic analogues (T2 and T3) revealed that these diterpenoids have antiandrogen properties that include inhibition of both androgen-dependent proliferation and AR transcriptional activity by a mechanism that involved competing with androgen for AR LBD and blocking essential N/C interactions required for androgen-induced AR transcriptional activity. Structure activity relationship analyses revealed some chemical features of T1 that are associated with activity and yielded T3 as the most potent analogue. In vivo, T3 significantly reduced the weight of seminal vesicles, which are an androgen-dependent tissue, thereby confirming T3’s on-target activity. The ability to create analogues of diterpenoids that have varying antiandrogen activity represents a novel class of chemical compounds for the analysis of AR ligand-binding properties and therapeutic development.

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Section: Discussionmentioning

confidence: 99%

Spongian Diterpenoids Inhibit Androgen Receptor Activity

Yang

Meimetis

Tien

et al. 2013

Molecular Cancer Therapeutics

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“…The cells were grown in MEM supplemented with 10% FBS, 100 units/ mL of penicillin, 100 mg/mL of streptomycin, 20 mg/ mL of l-glutamine, 0.14% NaHCO 3 , 1% each nonessential amino acid and a vitamin solution. The cytotoxicity of the essential oils and their components was examined in vitro with an tetrazolium-dye MTT (dimethylthiazol-2-yl]-2,5-diphenyl tetrazolium bromide) (Sigma, New Jersey, USA) assay, following a previously described protocol (Betancur-Galvis et al 2002). Briefly, cells were plated at 15 x 10 3 cells per well in a 96-well flatbottomed plate and incubated at 37 o C in a humidified incubator with 5% CO 2 .…”

Section: Methodsmentioning

confidence: 99%

Citral and carvone chemotypes from the essential oils of Colombian Lippia alba (Mill.) N.E. Brown: composition, cytotoxicity and antifungal activity

Mesa-Arango

Montiel-Ramos

Zapata

et al. 2009

Mem. Inst. Oswaldo Cruz

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118

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“…In addition to their anti-inflammatory activity, Spongia have also cytotoxic properties. Related agents, such as macrolide [24], furanoditerpene [25], polyketide [26], alkaloid, sesterterpene, triterpene, furanoterpene [10,27,28], diterpene [29], sesquiterpene and nucleoside [30], have already been isolated from other species of the genus Spongia .…”

Section: Discussionmentioning

confidence: 99%

Evaluation of antiproliferative and anti-inflammatory activities of methanol extract and its fractions from the Mediterranean sponge

Dellai

Deghrigue

Laroche-Clary

et al. 2012

Cancer Cell International

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BackgroundWithout doubt, natural products have been, and still are, the cornerstone of the health care armamentarium. Of all natural sources, the marine environment is clearly the last great frontier for pharmaceutical and medical research.MethodsThis work progresses in the direction of identifying component(s) from the Mediterranean sponge, Spongia officinalis with pharmacological activities. In the present study we investigated the efficacy of methanol extract and its semi-purified fractions (F2, F3) from Spongia officinalis for their in vivo anti-inflammatory activity using the carrageenan-induced paw edema in rats and their in vitro antiproliferative effects by their potential cytotoxic activity using the MTT colorimetric method and clonogenic inhibition against three human cancer cell lines (A549, lung cell carcinoma, HCT15, colon cell carcinoma and MCF7, breast adenocarcinoma).ResultsThe fractions F2 and F3 showed interesting anti-inflammatory and antiproliferative activities in a dose dependent manner.ConclusionsThe present study indicates that the methanolic extrac and its fractions from Spongia officinalis are a significant source of compounds with the antiproliferative and anti-inflammatory activities, and this may be useful for developing potential chemopreventive substances.

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Cytotoxic Effect (on Tumor Cells) and in Vitro Antiviral Activity against Herpes Simplex Virus of Synthetic Spongiane Diterpenes

Cited by 41 publications

References 16 publications

Spongian Diterpenoids Inhibit Androgen Receptor Activity

Spongian Diterpenoids Inhibit Androgen Receptor Activity

Citral and carvone chemotypes from the essential oils of Colombian Lippia alba (Mill.) N.E. Brown: composition, cytotoxicity and antifungal activity

Evaluation of antiproliferative and anti-inflammatory activities of methanol extract and its fractions from the Mediterranean sponge

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