Effects of natural and novel synthetic jasmonates in experimental metastatic melanoma

Reischer, Dorit; Heyfets, Alina; Shimony, Shai; Nordenberg, Jardena; Kashman, Yoel; Flescher, Eliezer

doi:10.1038/sj.bjp.0707146

Cited by 51 publications

(47 citation statements)

References 28 publications

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“…In the leukemic cell line, Molt-4, the cytotoxicity of methyl jasmonate (MJ) was shown to be transcription-and translation-independent (Flescher, 2005). In addition, the jasmonates are effective against drug-resistant cells Flescher, 2005;Reischer et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Methyl jasmonate binds to and detaches mitochondria-bound hexokinase

et al. 2008

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Section: Introductionmentioning

confidence: 99%

Methyl jasmonate binds to and detaches mitochondria-bound hexokinase

et al. 2008

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“…Likewise, it is reported the synthesis of numerous and varied series of derivatives of MeJA, predominantly halogenated (-Cl,-Br, -F) structures, which similar to JA and its derivatives, they exhibit interesting and in some cases potent anti-neoplastic properties (Ishii et al 2004;Reischer et al 2007;Park et al 2010;Zhao et al 2010), but it is noteworthy that in each of the proposed series does not have reported the production of derivatives with keto group reduced and the potential inhibition of cell growth observed with these series of compounds does not exceed the IC50 obtained with the derivatives reported here. Qian et al 2004 reported that synthetic hydroxyl-containing jasmonates may induce different levels of plant defense responses, which are associated with different levels of enhanced metabolic activity for secondary metabolite biosynthesis.…”

Section: Study On Tumor Cell Linesmentioning

confidence: 99%

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Carvajal¹,

Espinoza²,

Caggia³

et al. 2011

Electro Journal of Biotech

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Background: Several studies have shown that (-)-Jasmonic acid, (+)-7-iso-Jasmonic acid and its methyl ester, methyl jasmonate, have anti-cancer activity in vitro and in vivo, exhibiting selective cytotoxicity towards cancer cells. The degree of activity of these molecules is strongly related to their stereochemistry. The biotransformation of known compounds, natural or synthesized, related to interesting biological activities, generates new molecules displaying new improved properties compared with the original ones, increasing its value and providing new more effective products. Therefore, based on the above rationales and observations, in this work a biotransformation protocol to modify the chemical structure of the plant hormone jasmonic acid by using the fungus Gibberella fujikuroi was established. Results: The three jasmonic acid derivatives obtained, 3(S)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (1), 3(R)-Hydroxy-2(R)-(2Z-pentenyl)-cyclopentane-1(R)-acetic acid (2), 3-Hydroxy-2(S)-(2Z-pentenyl)-cyclopentane-1(S)-acetic acid (3), were tested for cell-growth inhibition activity towards the human cancer epithelial cell line, the oral squamous carcinoma cells (KB). The results obtained show that jasmonic acid derivatives (1-3) are active on human cancer cells examined in different concentration ranges, with IC50 value less than of 25 µM. The compound 3, with the same molecular structure of compounds 1 and 2, but with different stereochemistry, was more active confirming that the activity of jasmonate compounds is related to their stereochemistry and to substituents in the cyclopentane ring. In this study, we also tested the potential proapoptotic activity of compound 3, and our data suggest that it, as other jasmonate compounds, is able to trigger apoptotic death in cancer cells. This event may be correlated at an elevation of reactive oxygen species (ROS). Administration of N-acetylcysteine (NAC) prevented compound 3 cytotoxicity. Conclusions: This work shows for the by first time the production of hydroxylated derivatives of JA by biotransformation. The activity observed of these compounds in cancer cells is higher than the observed with JA and is strongly related to its stereochemistry.

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“…Jasmonate presented selective cytotoxicity in cancer cells in patients with chronic lymphocytic leukemia, leaving the nontransformed cells intact. 19,20 These compounds are poorly water-soluble, and cannot be administered intravenously or adequately absorbed by the body. However, for MJ, there are no studies on delivery systems that could circumvent these problems.…”

Section: Silva Et Almentioning

confidence: 99%

Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug

Silva¹,

Scarpa²,

Rossanezi³

et al. 2014

IJN

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Microemulsions (MEs) are colloidal systems that can be used for drug-delivery and drug-targeting purposes. These systems are able to incorporate drugs modifying bioavailability and stability and reducing toxic effects. The jasmonate compounds belong to a group of plant stress hormones, and the jasmonic acid and its methyl ester derivative have been described as having anticancer activity. However, these compounds are very poorly water-soluble, not allowing administration by an intravenous route without an efficient nanostructured carrier system. In this work, biocompatible MEs of appropriate diameter size for intravenous route administration, loaded and unloaded with methyl dihydrojasmonate (MJ), were developed and described in a pseudo-ternary phase diagram. The compositions of the MEs were carefully selected from their own regions in the pseudo-ternary phase diagram. The formulations were analyzed by light scattering, polarized light microscopy, and X-ray diffraction. Also, a study on rheological profile was performed. The results showed that the droplet size decreased with both MJ incorporation and oil phase/surfactant ratio. All compositions of the studied MEs showed rheological behavior of pseudoplastic fluid and amorphous structures. In the absence of MJ, most of the studied MEs had thixotropic characteristics, which became antithixotropic in the presence of the drug. Almost all MJ-unloaded MEs presented anisotropic characteristics, but some formulations became isotropic, especially in the presence of MJ. The results of this study support the conclusion that the studied system represents a promising vehicle for in vivo administration of the MJ antitumor drug.

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Effects of natural and novel synthetic jasmonates in experimental metastatic melanoma

Cited by 51 publications

References 28 publications

Methyl jasmonate binds to and detaches mitochondria-bound hexokinase

Methyl jasmonate binds to and detaches mitochondria-bound hexokinase

New stereoisomeric derivatives of jasmonic acid generated by biotransformation with the fungus Gibberella fujikuroi affect the viability of human cancer cells

Development and characterization of biocompatible isotropic and anisotropic oil-in-water colloidal dispersions as a new delivery system for methyl dihydrojasmonate antitumor drug

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