Comparative nuclease and anti-cancer properties of the naturally occurring malabaricones

Birija S. Patro; Mrityunjay Tyagi; Jayati Saha; Subrata Chattopadhyay

doi:10.1016/j.bmc.2010.08.011

Comparative nuclease and anti-cancer properties of the naturally occurring malabaricones

Birija S. Patro, Mrityunjay Tyagi, Jayati Saha, Subrata Chattopadhyay

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

The nuclease activities of the malabaricones have been studied so as to establish a structure-activity correlation and deduce the mechanistic pathway of the process. The inactivity of malabaricone A and malabaricone D revealed that the resorcinol moiety, present in the malabaricones did not contribute to the nuclease activity. Amongst the test compounds, malabaricone C (mal C) containing a B-ring catechol moiety showed significantly better Cu(II)-dependent nuclease activity than the partially methylated catechol derivative, mal B and curcumin. Mal C was found to bind efficiently with Cu(II) and DNA to facilitate the DNA nicking via a site-specifically generated Cu(I)-peroxo complex. Consistent with its Cu(II)-dependent nuclease property, mal C showed better cytotoxicity (IC₅₀ = 5.26 ± 1.20 μM) than curcumin (IC₅₀ = 24.46 ± 3.32 μM) against the MCF-7 human breast cancer cell line. The mal C-induced killing of the MCF-7 cells followed an apoptotic pathway involving oxidative damage to the cellular DNA.

Original language	English (US)
Pages (from-to)	7043-7051
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	18
Issue number	19
DOIs	https://doi.org/10.1016/j.bmc.2010.08.011
State	Published - Oct 1 2010
Externally published	Yes

Keywords

Anti-cancer
DNA cleavage
Malabaricone

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2010.08.011

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abstract = "The nuclease activities of the malabaricones have been studied so as to establish a structure-activity correlation and deduce the mechanistic pathway of the process. The inactivity of malabaricone A and malabaricone D revealed that the resorcinol moiety, present in the malabaricones did not contribute to the nuclease activity. Amongst the test compounds, malabaricone C (mal C) containing a B-ring catechol moiety showed significantly better Cu(II)-dependent nuclease activity than the partially methylated catechol derivative, mal B and curcumin. Mal C was found to bind efficiently with Cu(II) and DNA to facilitate the DNA nicking via a site-specifically generated Cu(I)-peroxo complex. Consistent with its Cu(II)-dependent nuclease property, mal C showed better cytotoxicity (IC50 = 5.26 ± 1.20 μM) than curcumin (IC50 = 24.46 ± 3.32 μM) against the MCF-7 human breast cancer cell line. The mal C-induced killing of the MCF-7 cells followed an apoptotic pathway involving oxidative damage to the cellular DNA.",

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AU - Patro, Birija S.

AU - Tyagi, Mrityunjay

AU - Saha, Jayati

AU - Chattopadhyay, Subrata

PY - 2010/10/1

Y1 - 2010/10/1

N2 - The nuclease activities of the malabaricones have been studied so as to establish a structure-activity correlation and deduce the mechanistic pathway of the process. The inactivity of malabaricone A and malabaricone D revealed that the resorcinol moiety, present in the malabaricones did not contribute to the nuclease activity. Amongst the test compounds, malabaricone C (mal C) containing a B-ring catechol moiety showed significantly better Cu(II)-dependent nuclease activity than the partially methylated catechol derivative, mal B and curcumin. Mal C was found to bind efficiently with Cu(II) and DNA to facilitate the DNA nicking via a site-specifically generated Cu(I)-peroxo complex. Consistent with its Cu(II)-dependent nuclease property, mal C showed better cytotoxicity (IC50 = 5.26 ± 1.20 μM) than curcumin (IC50 = 24.46 ± 3.32 μM) against the MCF-7 human breast cancer cell line. The mal C-induced killing of the MCF-7 cells followed an apoptotic pathway involving oxidative damage to the cellular DNA.

AB - The nuclease activities of the malabaricones have been studied so as to establish a structure-activity correlation and deduce the mechanistic pathway of the process. The inactivity of malabaricone A and malabaricone D revealed that the resorcinol moiety, present in the malabaricones did not contribute to the nuclease activity. Amongst the test compounds, malabaricone C (mal C) containing a B-ring catechol moiety showed significantly better Cu(II)-dependent nuclease activity than the partially methylated catechol derivative, mal B and curcumin. Mal C was found to bind efficiently with Cu(II) and DNA to facilitate the DNA nicking via a site-specifically generated Cu(I)-peroxo complex. Consistent with its Cu(II)-dependent nuclease property, mal C showed better cytotoxicity (IC50 = 5.26 ± 1.20 μM) than curcumin (IC50 = 24.46 ± 3.32 μM) against the MCF-7 human breast cancer cell line. The mal C-induced killing of the MCF-7 cells followed an apoptotic pathway involving oxidative damage to the cellular DNA.

KW - Anti-cancer

KW - DNA cleavage

KW - Malabaricone

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Comparative nuclease and anti-cancer properties of the naturally occurring malabaricones

Abstract

Keywords

UN SDGs

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