Interaction of curcumin with glutathione

Mathews, Susan; Rao, M. N. A.

doi:10.1016/0378-5173(91)90278-v

Cited by 28 publications

(18 citation statements)

References 5 publications

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“…Two of the studies imply the operation of such an interaction between curcumin and glutathione (GSH), but the products from the reactions are complex and ill-defined. 13,14 One investigation isolated two isomers from the combination of 1 and GSH separable by preparative high-performance liquid chromatography (HPLC). Both compounds by mass spectrometry furnished a molecu- lar weight (m/z) of 675.8, corresponding to a monoglutathionyl-curcumin adduct: 1-GSH.…”

Section: Michael Acceptors Increase Anticarcinogenic Potencymentioning

confidence: 99%

Highly Active Anticancer Curcumin Analogues

Mosley¹,

Liotta²,

Snyder³

2007

Advances in Experimental Medicine and Biology

133

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Curcumin, a compound in the human food supply, represents a near-perfect starting point for drug discovery. Consequently, a number of research groups have taken the natural product as a starting point to prepare and biologically evaluate a wide variety of curcumin analogues. One widely used structural modification truncates the central conjugated beta-diketone in curcumin to the monocarbonyl dienone. A diverse array of the latter compounds exhibit cytotoxicities against an equally diverse set of cancer-related cell lines. Importantly, these compounds still retain toxicity profiles in rodents comparable to the parent natural product, whereas some analogues (e.g., EF-24, 41) exhibit good oral bioavailability and good pharmacokinetics in mice. Thiol conjugates of EF-24 analogues have been prepared that address stability and solubility issues while demonstrating cellular activities similar to the unmodified dienones. In parallel experiments, the factor VIIa-tissue factor complex (fVIIa-TF) has been exploited to develop a targeting strategy for the analogues. In particular, the EF24-FFRck-fVIIa protein conjugate is not only somewhat more effective relative to the drug alone against breast cancer and melanocyte cells. Both simple curcumin analogues and the protein conjugate evidence antiangiogenic activity in cell culture. The implication is that the fVIIa-TF targeting process, like the dienone drugs, permits a double-pronged attack with the potential to destroy a tumor directly by apoptosis.

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Section: Michael Acceptors Increase Anticarcinogenic Potencymentioning

confidence: 99%

Highly Active Anticancer Curcumin Analogues

Mosley¹,

Liotta²,

Snyder³

2007

Advances in Experimental Medicine and Biology

133

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“…Incubation of curcumin with increasing concentrations of GSH led to a proportional (Mathews and Rao, 1991) and time-dependent (Awasthi et al, 2000) decrease in (Fig. 1A) and the trans and cis notations refer to the -C d -C g -C b -segment of the methine bridge (Kolev et al, 2005).…”

Section: H-bond Accepting Capacity Of the Methoxy Groupsmentioning

confidence: 99%

“…Michael additions to curcumin have been described for molecular targets such as reduced glutathione (GSH) (Mathews and Rao, 1991;Awasthi et al, 2000), glutathione S-transferase (GST) (van Iersel et al, 1996(van Iersel et al, , 1997, TrxR (Fang et al, 2005), interleukin (IL)-1 receptorassociated kinase (IRAK) (Jurrmann et al, 2005), the histone acetyltransferase E1A binding protein p300 (Marcu et al, 2006), calcium release-activated calcium channel protein 1 (Shin et al, 2012), and human ErbB-2 (HER2) , which is addressed separately in section III.E.1. The atoms through which the target molecules undergo a Michael addition include thiols (Mathews and Rao, 1991;Awasthi et al, 2000;Fang et al, 2005;Jurrmann et al, 2005) and selenols (Fang et al, 2005), both of which are mostly associated with a (seleno)cysteine residue.…”

Section: H-bond Accepting Capacity Of the Methoxy Groupsmentioning

confidence: 99%

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The Molecular Basis for the Pharmacokinetics and Pharmacodynamics of Curcumin and Its Metabolites in Relation to Cancer

Golen²,

et al. 2013

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“…103 This observation could be explained on the basis of a Michael-type addition reaction of GSH (as a nucleophile) in the chromophore region of curcumin (as an electrophile), which would result in the depletion of cellular GSH defense. 104 However, curcumin antioxidant activity still imparted some degree of GSH salvation, as GSH levels were shown to increase significantly in the pretreatment and posttreatment groups. 18 ISO administration resulted in an increase in the level of free radicals, which, in turn, induced cellular damage, and this observation could be substantiated by the low levels of free-radical scavenging enzymes such as catalase, superoxide dismutase, glutathione peroxidase, and glutathione-S-transferase (GST) that formed the first line of cellular defense against the oxidation injury.…”

Section: Antioxidant Effect Of Curcuminmentioning

confidence: 98%

Cardioprotective Effects of Curcumin

Miriyala

Panchatcharam²,

Rengarajulu³

Advances in Experimental Medicine and Biology

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Curcumin, a major active component of turmeric, is extracted from the powdered dry rhizome of Curcuma longa Linn (Zingiberaceae) and it has been used for centuries in indigenous medicine. We have shown that curcumin has a protective role against myocardial necrosis in rats. The antioxidant activity of curcumin could be attributed to the phenolic and methoxy groups in conjunction with the 1,3-diketone-conjugated diene system, for scavenging of the oxygen radicals. In addition, curcumin is shown to enhance the activities of detoxifying enzymes such as glutathione-S-transferase in vivo. We have also shown that oxygen free radicals exacerbate cardiac damage and curcumin induces cardioprotective effect and it also inhibits free-radical generation in myocardial ischemia in rats. This chapter on the cardioprotective effects of curcumin covers the following aspects: (1) the history of curcumin and its discovery as a potent drug with relevance to cardiovascular diseases; (2) mechanistic role of curcumin in vitro, emphasizing the antiplatelet and anticoagulant effects; (3) cardiovascular properties of curcumin; (4) application of curcumin in different animal models (viz. myocardial ischemia, myocardial infarction, cardiomyopathy, and arrhythmia in vitro and in vivo); (5) curcumin free-radical scavenging activity, particularly against O2 radical and depletion of the oxidative stress.

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Interaction of curcumin with glutathione

Cited by 28 publications

References 5 publications

Highly Active Anticancer Curcumin Analogues

Highly Active Anticancer Curcumin Analogues

The Molecular Basis for the Pharmacokinetics and Pharmacodynamics of Curcumin and Its Metabolites in Relation to Cancer

Cardioprotective Effects of Curcumin

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