A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (−)-epigallocatechin gallate [(−)-EGCG]

Lam, Wai Har; Kazi, Aslamuzzaman; Kuhn, Deborah J.; Chow, Larry M.C.; Chan, Albert S. C.; Dou, Q. Ping; Chan, Tak Hang

doi:10.1016/j.bmc.2004.08.002

Cited by 127 publications

(128 citation statements)

References 26 publications

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“…It has been shown that proteasome inhibitors cooperate with TRAIL in inducing apoptosis in cancers with over expression of bcl2 (Nencioni et al, 2005). Our results demonstrate that EGCG that has also been shown to act as a proteasome inhibitor (Lam et al, 2004;Landis-Piwowar et al, 2005) might actually synergize with TRAIL in inducing apoptosis in LNCaP cells. Interestingly our results suggest that pretreatment of cells with either EGCG or TRAIL does not result in modulation of expression of antiapoptotic molecules such as Bcl XL , and Bcl 2 , however, a combinatorial treatment led to twofold decrease in their expression (Figures 2b and 4) suggesting that both compounds act synergistically in repressing their expression.…”

Section: Discussionsupporting

confidence: 50%

Green tea polyphenol EGCG sensitizes human prostate carcinoma LNCaP cells to TRAIL-mediated apoptosis and synergistically inhibits biomarkers associated with angiogenesis and metastasis

et al. 2007

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Section: Discussionsupporting

confidence: 50%

Green tea polyphenol EGCG sensitizes human prostate carcinoma LNCaP cells to TRAIL-mediated apoptosis and synergistically inhibits biomarkers associated with angiogenesis and metastasis

et al. 2007

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“…7 Recently, it has been suggested that the peracetate of EGCG could be useful as a prodrug due to the limited stability and bioavailability of EGCG itself. 8 It has been reported that overexpression of 15-LO in human prostate cancer cells increases tumorigenesis. 9 Furthermore it is generally hypothesized that dietary polyphenols may reduce the risk of disorders associated with enhanced production of reactive oxygen and nitrogen species, such as coronary heart disease, stroke and inflammatory diseases as well as cancer.…”

Section: Figurementioning

confidence: 99%

Antioxidant activity of O-protected derivatives of (-)-epigallocatechin-3-gallate: inhibition of soybean and rabbit 15-lipoxygenases

Utenova¹,

Malterud²,

Rise³

2006

Arkivoc

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Abstract(-)-Epigallocatechin-3-gallate (EGCG) was protected at all eight phenolic groups as the methyl ether or acetate, propionate or butyrate esters. The synthetic derivatives were examined for antioxidant activities. The compounds were tested as potential diphenylpicrylhydrazyl (DPPH) radical scavengers and as inhibitors of 15-lipoxygenase (15-LO) enzymes from soybeans and rabbit reticulocytes. The O-protected EGCG derivatives were essentially inactive as DPPH scavengers but showed profound inhibiting effects on both types of 15-LO, and the inhibitory effects towards the two enzymes were significantly correlated. The O-protected EGCG derivatives inhibited 15-LO more strongly that EGCG itself. EGCG and its O-protected derivatives were also screened for antibacterial activity against M. tuberculosis.

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“…Purified Celastrol (>98%) was purchased from Calbiochem, Inc., (San Diego, CA). Synthesis of Pro-EGCG from (-)-EGCG was done as previously described (11,18). Daunorubicin, Cytarabine (Ara-C), Dimethylsulfoxide (DMSO) and trypan blue dye were purchased from Sigma-Aldrich (St. Louis, MO).…”

Section: Methodsmentioning

confidence: 99%

“…However, (-)-EGCG is relatively unstable under neutral or alkaline conditions. In an attempt to enhance the stability of (-)-EGCG, peracetate-protecting groups were introduced to the reactive hydroxyls to form Pro-EGCG (11).…”

Section: Introductionmentioning

confidence: 99%

Celastrol and an EGCG pro-drug exhibit potent chemosensitizing activity in human leukemia cells

et al. 2010

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Abstract. Chemotherapy remains the staple of treatment for many types of leukemia. Despite the positive impact on extending overall survival in patients with hematological malignancies, new treatment strategies are needed to reduce the nonspecific toxicity and improve the efficacy of treatment. Celastrol, derived from the 'Thunder God Vine' and Pro-EGCG, a pre-drug version of green tea polyphenol EGCG have shown potent biological activity in vitro and in vivo. Whether these natural products augment the efficacy of conventional chemotherapy in the treatment of leukemia cells has yet to be demonstrated. Here we demonstrate that these natural products could sensitize the effect of chemotherapy in both K-562 and Jurkat T human leukemia cells. Accordingly, this potent biological activity was associated with increased levels of leukemia cell killing, caspase 3 activation, and poly(ADPribose) polymerase cleavage. Furthermore, the higher levels of apoptotic indices were associated with decreased levels of Bcr-Abl oncoprotein in K-562 cells. Taken together, our findings present a compelling rationale for the development of combination strategies using natural products in the treatment of hematological malignancies.

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A potential prodrug for a green tea polyphenol proteasome inhibitor: evaluation of the peracetate ester of (−)-epigallocatechin gallate [(−)-EGCG]

Cited by 127 publications

References 26 publications

Green tea polyphenol EGCG sensitizes human prostate carcinoma LNCaP cells to TRAIL-mediated apoptosis and synergistically inhibits biomarkers associated with angiogenesis and metastasis

Green tea polyphenol EGCG sensitizes human prostate carcinoma LNCaP cells to TRAIL-mediated apoptosis and synergistically inhibits biomarkers associated with angiogenesis and metastasis

Antioxidant activity of O-protected derivatives of (-)-epigallocatechin-3-gallate: inhibition of soybean and rabbit 15-lipoxygenases

Celastrol and an EGCG pro-drug exhibit potent chemosensitizing activity in human leukemia cells

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