Synthesis of 4′-ester analogs of resveratrol and their evaluation in malignant melanoma and pancreatic cell lines

Wong, Yong; Osmond, Gregory W.; Brewer, Kenneth I.; Tyler, Douglas S.; Andrus, Merritt B.

doi:10.1016/j.bmcl.2009.12.006

Cited by 20 publications

(14 citation statements)

References 19 publications

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Section: Resveratrol and Skin Diseases: Promises And Prospectsmentioning

confidence: 99%

“…For example, Wong et al synthesized 4'-ester analogs of resveratrol via decarbonylative Heck coupling to assemble the protected stilbene core structure [75]. These analogs were then tested against melanoma cells [75]. It was found that four of the synthesized compounds are more effective in killing the melanoma cells than resveratrol, and that two out of four compounds had no cytotoxic effects on normal human dermal fibroblasts.…”

Section: Resveratrol and Skin Diseases: Promises And Prospectsmentioning

confidence: 99%

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The grape antioxidant resveratrol for skin disorders: Promise, prospects, and challenges

Ndiaye¹,

Philippe²,

Mukhtar³

et al. 2011

Archives of Biochemistry and Biophysics

169

119

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Resveratrol, a phytoalexin antioxidant found in red grapes, has been shown to have both chemopreventive and therapeutic effects against many diseases and disorders, including those of the skin. Studies have shown protective effects of resveratrol against ultraviolet radiation mediated oxidative stress and cutaneous damages including skin cancer. Because many of the skin conditions stem from ultraviolet radiation and oxidative stress, this antioxidant appears to have promise and prospects against a wide range of cutaneous disorders including skin aging and skin cancers. However, there are a few roadblocks in the way of this promising agent regarding its translation from the bench to the bedside. This review discusses the promise and prospects of resveratrol in the management of skin disorders and the associated challenges.

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Section: Resveratrol and Skin Diseases: Promises And Prospectsmentioning

confidence: 99%

Section: Resveratrol and Skin Diseases: Promises And Prospectsmentioning

confidence: 99%

The grape antioxidant resveratrol for skin disorders: Promise, prospects, and challenges

Ndiaye¹,

Philippe²,

Mukhtar³

et al. 2011

Archives of Biochemistry and Biophysics

169

119

View full text Add to dashboard Cite

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“…Other modifications of the aromatic rings of resveratrol have been developed, notably addition of more hydroxy groups or acyloxy groups as substituents were found to be effective. In this regard, E -3,4,5,4’-tetrahydroxystilbene (at 500 nM) activated apoptosis in transformed fibroblasts with 100-fold higher potency than in non-transformed fibroblasts (27), while trans -resveratrol analogues bearing various acyl residues at C-4’ were effective in the 10-50 µM range with human melanoma and pancreatic cancer cells (28). …”

Section: Introductionmentioning

confidence: 99%

Anti-tumor properties of cis-resveratrol methylated analogs in metastatic mouse melanoma cells

et al. 2015

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Resveratrol (E-3,5,4’-trihydroxystilbene) is a polyphenol found in red wine that has been shown to have multiple anti-cancer properties. Although cis (Z) and trans (E) isomers of resveratrol occur in nature, the cis form is not biologically active. However, methylation at key positions of the cis form results in more potent anti-cancer properties. This study determined that synthetic cis-polymethoxystilbenes (methylated analogues of cis-resveratrol) inhibited cancer-related phenotypes of metastatic B16 F10 and non-metastatic B16 F1 mouse melanoma cells. In contrast with cis or trans-resveratrol and trans-polymethoxystilbene which were ineffective at 10 μM, cis-polymethoxystilbenes inhibited motility and proliferation of melanoma cells with low micromolar specificity (IC50 <10 μM). Inhibitory effects by cis-polymethoxystilbenes were significantly stronger with B16 F10 cells and were accompanied by decreased expression of β-tubulin and pleckstrin homology domain-interacting protein, a marker of metastatic B16 cells. Thus, cis-polymethoxystilbenes have potential as chemotherapeutic agents for metastatic melanoma.

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“…We have previously reported that RESV is selectively and considerably cytotoxic to malignantly transformed melanocytes, sparing normal human fibroblasts [9,10]. However, the impressive in vitro effects of RESV did not translate to a mouse xenograft model, with administration of daily intraperitoneal injections [10].…”

Section: Introductionmentioning

confidence: 99%

In vitro and in vivo evaluation of resveratrol and 3,5-dihydroxy-4'-acetoxy-trans-stilbene in the treatment of human prostate carcinoma and melanoma

Osmond¹,

Masko²,

Tyler³

et al. 2013

Journal of Surgical Research

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Synthesis of 4′-ester analogs of resveratrol and their evaluation in malignant melanoma and pancreatic cell lines

Cited by 20 publications

References 19 publications

The grape antioxidant resveratrol for skin disorders: Promise, prospects, and challenges

The grape antioxidant resveratrol for skin disorders: Promise, prospects, and challenges

Anti-tumor properties of cis-resveratrol methylated analogs in metastatic mouse melanoma cells

In vitro and in vivo evaluation of resveratrol and 3,5-dihydroxy-4'-acetoxy-trans-stilbene in the treatment of human prostate carcinoma and melanoma

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